(1S,3S,3aR,7aS)-1-ethenyl-1,2,3,3a,7,7a-hexahydro-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylene-4H-inden-4-one | 216753-27-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3S,3aR,7aS)-1-ethenyl-1,2,3,3a,7,7a-hexahydro-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylene-4H-inden-4-one
• 英文别名: (1S,3S,3aR,4S,7aS)-1,2,3,3a,7,7a-hexahydro-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-(vinyl)inden-4-one；(1S,3S,3aR,7aS)-1,2,3,3a,7,7a-hexahydro-3-(3-hydroxy-4-methoxybenzyl)-7-methylene-1-vinylindene-4-one；(+)-ottelione A；ottelione A；RPR112378；RPR-112378；(1S,3S,3aR,7aS)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1H-inden-4-one
• CAS: 216753-27-4
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: ODHHTIYRUDURPW-IPZZXCBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3S,3aR,7aS)-1-ethenyl-1,2,3,3a,7,7a-hexahydro-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylene-4H-inden-4-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 以83%的产率得到(1S,3S,3aS,7aS)-1-ethenyl-1,2,3,3a,7,7a-hexahydro-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylene-4H-inden-4-one
  参考文献：
  名称：

  （+）-和（-）-ottelione A和（+）-和（-）-ottelione B的对映选择性总合成。具有生物活性的新型天然产物的绝对构型

  摘要：

  继我们最近以消旋形式对具有生物活性的天然产物otteliones A和B的全合成后，我们现在通过对映异构策略从现成的环戊二烯的Diels-Alder加成物中完成了otteliones A和B的对映体的全合成。和对苯醌。这些努力导致阐明了天然存在的蝶毛虫A和B的绝对构型。

  DOI：

  10.1016/s0040-4039(03)01643-5
• 作为产物：
  描述：

  (1S,3S,3aR,4S,7aS)-3-(3-dichloroacetoxy-4-methoxybenzyl)-1,2,3,3a,7,7a-hexahydro-7-methylene-1-(vinyl)inden-4-one 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到(1S,3S,3aR,7aS)-1-ethenyl-1,2,3,3a,7,7a-hexahydro-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylene-4H-inden-4-one
  参考文献：
  名称：

  otteliones A和B，来自淡水植物的新型有效抗肿瘤剂的总合成和绝对构型。

  摘要：

  [反应：见正文]虫A和B的第一个对映选择性全合成已成功实现，这是生物学上重要的，结构上新颖的天然产物。该总合成充分证实了这些天然产物的绝对构型。

  DOI：

  10.1021/ol035443x

文献信息

• Enantioselective total syntheses of (+)- and (−)-ottelione A and (+)- and (−)-ottelione B. Absolute configuration of the novel, biologically active natural products
  作者：Goverdhan Mehta、Kabirul Islam

  DOI：10.1016/s0040-4039(03)01643-5

  日期：2003.8

  recent total synthesis of the biologically potent natural products otteliones A and B in racemic form, we have now accomplished the total synthesis of both the enantiomers of otteliones A and B through an enantiodivergent strategy emanating from the readily available Diels–Alder adduct of cyclopentadiene and p-benzoquinone. These endeavors have led to the elucidation of the absolute configuration of naturally

  继我们最近以消旋形式对具有生物活性的天然产物otteliones A和B的全合成后，我们现在通过对映异构策略从现成的环戊二烯的Diels-Alder加成物中完成了otteliones A和B的对映体的全合成。和对苯醌。这些努力导致阐明了天然存在的蝶毛虫A和B的绝对构型。
• Total Synthesis and Absolute Configuration of Otteliones A and B, Novel and Potent Antitumor Agents from a Freshwater Plant
  作者：Hiroshi Araki、Munenori Inoue、Tadashi Katoh

  DOI：10.1021/ol035443x

  日期：2003.10.1

  [reaction: see text] The first enantioselective total synthesis of otteliones A and B, biologically important and structurally novel natural products, has been successfully achieved. This total synthesis fully confirms the absolute configuration of these natural products.

  [反应：见正文]虫A和B的第一个对映选择性全合成已成功实现，这是生物学上重要的，结构上新颖的天然产物。该总合成充分证实了这些天然产物的绝对构型。
• Modified chalcone compounds as antimitotic agents
  申请人：Arizona Biomedical Research Commission

  公开号：EP2447248A2

  公开（公告）日：2012-05-02

  Antimitotic agents comprising a modified chalcone or modified chalcone derivative are disclosed. The modified chalcone or modified chalcone derivative compounds are of the general formula CHAL-LIN-COV, wherein CHAL is a chalcone or chalcone derivative portion, LIN is an optional linker portion, and COV is a covalent bonding portion (e.g., an a,ss-unsaturated thiol ester group). The modified chalcone or modified chalcone derivative compounds provide an improved method of interference with tubulin polymerization, for example by covalent (and essentially irreversible) bonding between tubulin and the covalent bonding portion, potentially resulting in a decrease in tumor size and/or disappearance of the cancer, to the benefit of cancer patients.

  本发明公开了包含改性查尔酮或改性查尔酮衍生物的抗硝化剂。改性查尔酮或改性查尔酮衍生物化合物的通式为 CHAL-LIN-COV，其中 CHAL 为查尔酮或查尔酮衍生物部分，LIN 为任选连接部分，COV 为共价键部分（例如，a,s-不饱和硫醇酯基）。改性查尔酮或改性查尔酮衍生物化合物提供了一种改进的干扰小管蛋白聚合的方法，例如通过小管蛋白与共价键部分之间的共价键（且基本上不可逆），可能导致肿瘤体积减小和/或癌症消失，从而使癌症患者受益。
• Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms
  作者：Derrick L. J. Clive、Dazhan Liu

  DOI：10.1021/jo702635t

  日期：2008.4.1

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.
• Synthesis of the Otteliones A and B: Use of a Cyclopropyl Group as Both a Steric Shield and a Vinyl Equivalent
  作者：Derrick L. J. Clive、Dazhan Liu

  DOI：10.1002/anie.200700517

  日期：2007.5.11