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Revision as of 08:48, 20 December 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey← Previous edit Latest revision as of 11:33, 1 June 2023 edit undoGraeme Bartlett (talk | contribs)Administrators249,701 edits added Category:Oxygen heterocycles using HotCat 
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{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 414650012
| Watchedfields = changed
⚫ | ImageFile = cavicularin.png
⚫ | verifiedrevid = 466832860
⚫ | ImageFile = Cavicularin.svg
| ImageSize = 200px | ImageSize = 200px
| IUPACName = 9,10,18,19-Tetrahydro-5,8:15,17-diethenobenzonaphthoxacyclotetradecin-3,12,21-triol | IUPACName = 9,10,18,19-Tetrahydro-5,8:15,17-diethenobenzonaphthoxacyclotetradecin-3,12,21-triol
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 178734-41-3 | CASNo = 178734-41-3
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem =
| UNII = B6Y87G6TOX
⚫ | ChemSpiderID = 26323925
⚫ | PubChem = 11316166
⚫ | SMILES = c1cc2ccc1CCc3cc(ccc3-c4c(ccc5c4-c6cc(c(cc6CC5)O)O2)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | InChI = 1/C28H22O4/c29-20-8-11-22-18(13-20)4-1-16-2-9-21(10-3-16)32-26-15-23-19(14-25(26)31)6-5-17-7-12-24(30)28(22)27(17)23/h2-3,7-15,29-31H,1,4-6H2
⚫ | ChemSpiderID = 9491133
| InChIKey = URQGPPCZQAUJRX-UHFFFAOYAK
⚫ | SMILES = c1cc2ccc1CCc3cc(ccc3-c4cc-5c(cc4O)CCc6c5c(c(cc6)O)O2)O
⚫ | StdInChI = 1S/C28H22O4/c29-20-8-11-22-18(13-20)4-1-16-2-9-21(10-3-16)32-26-15-23-19(14-25(26)31)6-5-17-7-12-24(30)28(22)27(17)23/h2-3,7-15,29-31H,1,4-6H2
⚫ | InChI = 1/C28H22O4/c29-20-8-11-22-18(13-20)4-1-16-2-9-21(10-3-16)32-28-25(30)12-7-17-5-6-19-14-26(31)24(22)15-23(19)27(17)28/h2-3,7-15,29-31H,1,4-6H2
⚫ | StdInChIKey = URQGPPCZQAUJRX-UHFFFAOYSA-N
| InChIKey = MCFLLKAHGNIXPF-UHFFFAOYAB
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | StdInChI = 1S/C28H22O4/c29-20-8-11-22-18(13-20)4-1-16-2-9-21(10-3-16)32-28-25(30)12-7-17-5-6-19-14-26(31)24(22)15-23(19)27(17)28/h2-3,7-15,29-31H,1,4-6H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ | StdInChIKey = MCFLLKAHGNIXPF-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=28 | H=22 | O=4 | C=28 | H=22 | O=4
| Appearance = | Appearance =
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| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}


'''Cavicularin''' is a ]ic ] isolated from the ] '']''. This ] is unusual because it was the first compound isolated from nature displaying ] due to the presence of ] and ]. The ] for (+)-cavicularin is +168.2°.<ref>{{cite journal | title = (+)-Cavicularin: A Novel Optically Active Cyclic Bibenzyl-Dihydrophenanthrene Derivative from the Liverwort Cavicularia densa Steph | author = M. Toyota, T. Yoshida, Y. Kan, S. Takaoka, Y. Asakawa | journal = Tetrahedron Letters | year = 1996 | pages = 4745–4748 | url = http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THS-3V99257-14&_user=1065764&_handle=V-WA-A-W-CD-MsSAYVA-UUA-U-AAWAUAUZVD-AAAYCEAVVD-AZVWVYEDB-CD-U&_fmt=summary&_coverDate=07%2F01%2F1996&_rdoc=32&_orig=browse&_srch=%23toc%235290%231996%23999629972%2339771!&_cdi=5290&view=c&_acct=C000051225&_version=1&_urlVersion=0&_userid=1065764&md5=4e93161113dd5af8dad768dd3c3d842a | doi = 10.1016/0040-4039(96)00956-2 | volume = 37 | issue = 27}}</ref> It is also a very ] molecule. It incorporates a benzene ring that is bent 17° out of planarity. This type of ] in aromatic compounds is normally reserved for synthetic ]s. '''Cavicularin''' is a ]ic ] isolated from the ] '']''. This ] is unusual because it was the first compound isolated from nature displaying ] solely due to the presence of ] and ]. The ] for (+)-cavicularin is +168.2°.<ref>{{cite journal | title = (+)-Cavicularin: A Novel Optically Active Cyclic Bibenzyl-Dihydrophenanthrene Derivative from the Liverwort Cavicularia densa Steph |author1=M. Toyota |author2=T. Yoshida |author3=Y. Kan |author4=S. Takaoka |author5=Y. Asakawa | journal = Tetrahedron Letters | year = 1996 | pages = 4745–4748 | doi = 10.1016/0040-4039(96)00956-2 | volume = 37 | issue = 27}}{{dead link|date=March 2019|bot=medic}}{{cbignore|bot=medic}}</ref> It is also a very ] molecule. The ''para''-substituted phenol ring is bent about 15° out of planarity, adopting a somewhat ]. This type of ] in aromatic compounds is normally reserved for synthetic ]s.


:]{{clear-left}} ]


The ] was obtained from ] in the district of ]. The material was dried for one day, ground to a powder and 5&nbsp;grams were ]ed in ] for 4 months to yield 2.5&nbsp;mg (0.049%) of cavicularin after ] and ]. In 2005, the compound was prepared by ] together with the unstrained compound '''riccardin C'''.<ref>{{cite journal | title = Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration | author = David C. Harrowven, Timothy Woodcock , Peter D. Howes | journal = Angewandte Chemie | volume = 44 | issue = 25 | pages = 3899–3901 | year = 2005 | url = http://www3.interscience.wiley.com/cgi-bin/abstract/110498256/ABSTRACT | doi = 10.1002/anie.200500466 | pmid = 15900530}}</ref><ref>Kostiuk, S. L., Woodcock, T., Dudin, L. F., Howes, P. D. and Harrowven, D. C. (2011), Unified Syntheses of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene Adopting a Boat Configuration. Chemistry - A European Journal, 17: 10906–10915. {{doi|10.1002/chem.201101550}}</ref> The ] was obtained from ] in the district of ]. The material was dried for one day, ground to a powder and 5&nbsp;grams were ]ed in ] for 4 months <sup></sup> to yield 2.5&nbsp;mg (0.049%) of cavicularin after ] and ].


== Total synthesis ==
:]{{clear-left}}
In 2005<ref>{{cite journal | title = Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration |author1=David C. Harrowven |author2=Timothy Woodcock |author3=Peter D. Howes | journal = Angewandte Chemie | volume = 44 | issue = 25 | pages = 3899–3901 | year = 2005 | doi = 10.1002/anie.200500466 | pmid = 15900530}}</ref> and again in 2011,<ref>{{cite journal | last1 = Kostiuk | first1 = S. L. | last2 = Woodcock | first2 = T. | last3 = Dudin | first3 = L. F. | last4 = Howes | first4 = P. D. | last5 = Harrowven | first5 = D. C. | year = 2011 | title = Unified Syntheses of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene Adopting a Boat Configuration | journal = Chemistry: A European Journal | volume = 17 | issue = 39| pages = 10906–10915 | doi = 10.1002/chem.201101550 | pmid = 21932232 }}</ref> the compound was prepared by ] together with the unstrained compound ]. In 2013, several other syntheses were reported for it<ref>{{cite journal | last1 = Takiguchi | first1 = H. | last2 = Ohmori | first2 = K. | last3 = Suzuki | first3 = K. | year = 2013 | title = Synthesis and Determination of the Absolute Configuration of Cavicularin by a Symmetrization/Asymmetrization Approach | journal = Angew. Chem. Int. Ed. | volume = 52 | issue = 40| pages = 10472–10476 | doi = 10.1002/anie.201304929 | pmid = 23956143 }}</ref><ref>{{cite journal | last1 = Zhao | first1 = Peng | last2 = Beaudry | first2 = Christopher M. | year = 2013 | title = Total Synthesis of (±)-Cavicularin: Control of Pyrone Diels–Alder Regiochemistry Using Isomeric Vinyl Sulfones | journal = Organic Letters | volume = 15 | issue = 2| pages = 402–405 | doi = 10.1021/ol303390a | pmid=23301524}}</ref> and a racemic synthesis.<ref>{{cite journal | last1 = Harada | first1 = Kenichi | last2 = Makino | first2 = Kosho | last3 = Shima | first3 = Naoki | last4 = Okuyama | first4 = Haruka | last5 = Esumi | first5 = Tomoyuki | last6 = Kubo | first6 = Miwa | last7 = Hioki | first7 = Hideaki | last8 = Asakawa | first8 = Yoshinori | last9 = Fukuyama | first9 = Yoshiyasu | year = 2013 | title = Total synthesis of riccardin C and (±)-cavicularin via Pd-catalyzed Ar–Ar cross couplings | journal = Tetrahedron | volume = 69 | issue = 34| pages = 6959–6968 | doi = 10.1016/j.tet.2013.06.064 }}</ref>


== References == == References ==
{{reflist}} {{reflist|2}}


{{Dihydrostilbenoid}}
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{{Phenanthrenes}}

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