(1R,2S,3R,4S)-<3--2-bornyl>-2-oxo-cyclohexenecarboxylate | 170211-93-5

• 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: (1R,2S,3R,4S)-<3--2-bornyl>-2-oxo-cyclohexenecarboxylate
• 英文别名: [(1R,2S,3R,4S)-3-[N-(benzenesulfonyl)-3,5-dimethylanilino]-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 6-oxocyclohexene-1-carboxylate
• CAS: 170211-93-5
• 化学式: C₃₁H₃₇NO₅S
• 分子量: 535.704
• InChiKey: BTLFQKHPKPIOHG-JBGDWIKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-溴丙烯 、 (1R,2S,3R,4S)-<3--2-bornyl>-2-oxo-cyclohexenecarboxylate 在 叔丁基锂 、 lithium,azanidylidenemethylidenecopper,2H-thiophen-2-ide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到(1R,2S,3R,4S)-<3--2-bornyl>-(6R)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate
  参考文献：
  名称：

  Enantiomerically Pure 6-Substituted 2-Oxo-cyclohexanecarboxylates by Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates

  摘要：

  Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols In and Ix and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 degrees C and deprotection by methanolysis gave enantiomerically pure 6-substituted 2-oxo-cyclohexanecarboxylates 14-19 and ent-14-19, valuable as chiral building blocks in natural product synthesis.

  DOI：

  10.1016/0040-4020(95)00676-y
• 作为产物：
  描述：

  2-hydroxy-1-cyclohexenecarboxylic acid ethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 52.0h， 生成 (1R,2S,3R,4S)-<3--2-bornyl>-2-oxo-cyclohexenecarboxylate
  参考文献：
  名称：

  Enantiomerically Pure 6-Substituted 2-Oxo-cyclohexanecarboxylates by Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates

  摘要：

  Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols In and Ix and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 degrees C and deprotection by methanolysis gave enantiomerically pure 6-substituted 2-oxo-cyclohexanecarboxylates 14-19 and ent-14-19, valuable as chiral building blocks in natural product synthesis.

  DOI：

  10.1016/0040-4020(95)00676-y

文献信息

• EPC Synthesis of 6-Substituted 2-Oxo-cyclohexanecarboxylates via Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates
  作者：E Urban

  DOI：10.1016/00404-0399(50)0886h-

  日期：1995.7.3
• Diastereoselective Aziridination of Chiral α-Carbonyl Enoates¹
  作者：Stefania Fioravanti、Alberto Morreale、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1021/jo025670x

  日期：2002.7.1

  Nosyloxycarbamates very efficiently aziridinate optically active a-carbonyl enoates with high levels of diastereoselectivity under mild conditions and in a straightforward process.
• Enantiomerically Pure 6-Substituted 2-Oxo-cyclohexanecarboxylates by Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates
  作者：Ernst Urban、Gerhard Richs、Guido Knühl

  DOI：10.1016/0040-4020(95)00676-y

  日期：1995.10

  Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols In and Ix and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 degrees C and deprotection by methanolysis gave enantiomerically pure 6-substituted 2-oxo-cyclohexanecarboxylates 14-19 and ent-14-19, valuable as chiral building blocks in natural product synthesis.