(1S,2R,5R)-2-Hydroxy-5-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopentanecarboxylic acid methyl ester | 552320-57-7

• 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,2R,5R)-2-Hydroxy-5-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopentanecarboxylic acid methyl ester
• 英文别名: methyl (1S,2R,5R)-2-hydroxy-5-[[(1S,2R,4R)-2-methoxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methylsulfanyl]cyclopentane-1-carboxylate
• CAS: 552320-57-7
• 化学式: C₁₈H₃₀O₄S
• 分子量: 342.5
• InChiKey: QVHFCKSJFWYKHH-PCBKOEHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R)-2-Hydroxy-5-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopentanecarboxylic acid methyl ester 在 镍 作用下， 以 甲醇 为溶剂， 以83%的产率得到甲基(1S,2R)-2-羟基环戊烷羧酸酯
  参考文献：
  名称：

  Asymmetric Michael–aldol tandem cyclization of ω-oxo-α,β-unsaturated esters with 10-mercaptoisoborneol methyl ether

  摘要：

  The asymmetric reaction of omega-oxo-alpha,beta-unsaturated esters with lithium chiral thiolates afforded the Michael-aldol tandem cyclization products in high yield and good stereo selectivity. Reductive desulfurization gave the corresponding optically pure 2-hydroxycycloalkanecarboxylates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00253-3
• 作为产物：
  描述：

  (1S,2R,5R)-2-((1S,2R,4R)-2-Methoxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-5-phenylcarbamoyloxy-cyclopentanecarboxylic acid methyl ester 在 三氯硅烷 、 三乙胺 作用下， 以 苯 为溶剂， 反应 12.0h， 以99%的产率得到(1S,2R,5R)-2-Hydroxy-5-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylsulfanyl)-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Michael–aldol tandem cyclization of ω-oxo-α,β-unsaturated esters with 10-mercaptoisoborneol methyl ether

  摘要：

  The asymmetric reaction of omega-oxo-alpha,beta-unsaturated esters with lithium chiral thiolates afforded the Michael-aldol tandem cyclization products in high yield and good stereo selectivity. Reductive desulfurization gave the corresponding optically pure 2-hydroxycycloalkanecarboxylates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00253-3