(1R,2R,3R,5S,6S)-2,3-dihydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester | 188885-73-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R,3R,5S,6S)-2,3-dihydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester
• 英文别名: ethyl (1R,2R,3R,5S,6S)-2,3-dihydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylate
• CAS: 188885-73-6
• 化学式: C₉H₁₂O₅
• 分子量: 200.191
• InChiKey: DOYAOYBNARKQCO-USOLSPIOSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  341.8±42.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,5S,6S)-2,3-dihydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 在 palladium on activated charcoal 甲基磺酰氯 、 三乙胺 、 氢气 、 N,N-二异丙基乙胺 作用下， 以57%的产率得到(1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  萜烯A和B的合成：使用环丙基作为空间屏蔽和乙烯基等同物。

  摘要：

  DOI：

  10.1002/anie.200700517
• 作为产物：
  描述：

  ethyl (1R,2R,3S,4S,6R)-5-oxospiro[7,9-dioxatricyclo[4.3.0.02,4]nonane-8,1'-cyclohexane]-3-carboxylate 在 三氟乙酸 作用下， 以50%的产率得到(1R,2R,3R,5S,6S)-2,3-dihydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Asymmetric synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740)

  摘要：

  The asymmetric synthesis of(+)-2-aminobicyclo[3.1.0]hexane-2, 6-dicarboxylic acid (LY354740) 1, a potent and selective group 2 mGluR agonist, has been accomplished starting from the readily available enantiomerically pure cyclopentenone 4. Thus, cyclopropanation with ethyl(dimethylsulfuranylidene)acetate generated in situ with DBU, followed by deketalization gave rise to the dihydroxy bicyclic ketone 9. After protecting the ketone as 1,3-dioxolane and its transformation to the orthoformate 11, this was pyrolytically deoxygenated in a sealed tube to the bicyclic enone 13. The Synthesis was completed after hydrogenation, stereoselective Bucherer-Bergs reaction and hydantoin hydrolysis, yielding LY354740 (+)-1 with an e.e. greater than or equal to 98%. (C) 1997 Elsevier Science Ltd. rights reserved.

  DOI：

  10.1016/s0957-4166(97)00001-3

文献信息

• 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.