(1S,4S,5R)-5-chloro-4-(-)-menthyloxy-3-oxabicyclo[3.2.0]heptan-2-one | 185122-89-8

• 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,4S,5R)-5-chloro-4-(-)-menthyloxy-3-oxabicyclo[3.2.0]heptan-2-one
• 英文别名: (1S,4S,5R)-5-chloro-4-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3-oxabicyclo[3.2.0]heptan-2-one
• CAS: 185122-89-8
• 化学式: C₁₆H₂₅ClO₃
• 分子量: 300.826
• InChiKey: ZCCDYPDJOROTBF-KDNIGHMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基锂 、 (1S,4S,5R)-5-chloro-4-(-)-menthyloxy-3-oxabicyclo[3.2.0]heptan-2-one 在 cerium(III) chloride 作用下， 生成 2-[(1R,2R)-2-(1-Hydroxy-1-methyl-ethyl)-cyclobutyl]-propan-2-ol
  参考文献：
  名称：

  Synthesis and characterization of both enantiomers of trans-1,2-di-(2-hydroxy-2-propyl)-cyclobutane

  摘要：

  Both enantiomers of the title compound are synthesized for the first time in four steps including a [2+2]-photocycloaddition to build up the cyclobutane backbone and a cerium supported reductive permethylation. During the cerium supported process a complete and selective change in the configuration of the cyclobutane ring takes place. The substituents are transformed from the cis- to the trans-geometry. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00386-2
• 作为产物：
  描述：

  L-薄荷醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 (1S,4S,5R)-5-chloro-4-(-)-menthyloxy-3-oxabicyclo[3.2.0]heptan-2-one
  参考文献：
  名称：

  Synthesis and characterization of both enantiomers of trans-1,2-di-(2-hydroxy-2-propyl)-cyclobutane

  摘要：

  Both enantiomers of the title compound are synthesized for the first time in four steps including a [2+2]-photocycloaddition to build up the cyclobutane backbone and a cerium supported reductive permethylation. During the cerium supported process a complete and selective change in the configuration of the cyclobutane ring takes place. The substituents are transformed from the cis- to the trans-geometry. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00386-2

文献信息

• Synthesis and characterization of both enantiomers of trans-1,2-di-(2-hydroxy-2-propyl)-cyclobutane
  作者：Frank W. Curtius、Hans-Dieter Scharf

  DOI：10.1016/0957-4166(96)00386-2

  日期：1996.10

  Both enantiomers of the title compound are synthesized for the first time in four steps including a [2+2]-photocycloaddition to build up the cyclobutane backbone and a cerium supported reductive permethylation. During the cerium supported process a complete and selective change in the configuration of the cyclobutane ring takes place. The substituents are transformed from the cis- to the trans-geometry. Copyright (C) 1996 Published by Elsevier Science Ltd