(3R)-5-cyclohexylsulfanyl-3-methyl-5-oxopentanoic acid | 1042981-58-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R)-5-cyclohexylsulfanyl-3-methyl-5-oxopentanoic acid
• CAS: 1042981-58-7
• 化学式: C₁₂H₂₀O₃S
• 分子量: 244.355
• InChiKey: AKPPZYVFYRFUDS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-5-cyclohexylsulfanyl-3-methyl-5-oxopentanoic acid 在 lithium hydroxide 、 sodium tetrahydroborate 、 lithium perchlorate 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 (S)-5-Hydroxy-3-methyl-pentanoic acid
  参考文献：
  名称：

  Organocatalytic Asymmetric Addition of Alcohols and Thiols to Activated Electrophiles: Efficient Dynamic Kinetic Resolution and Desymmetrization Protocols

  摘要：

  [GRAPHICS]Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile. The optimum catalyst is remarkably insensitive to the steric bulk of the amino acid residue, allowing alanine, methionine, and phenylalanine-derived azalactones to undergo DKR with unprecedented levels of enantio selectivity using a synthetic catalyst. The first DKR of these substrates by thiols and the highly enantioselective desymmetrization of a meso-glutaric anhydride by thiolysis are also reported.

  DOI：

  10.1021/jo801158g
• 作为产物：
  描述：

  3-甲基戊二酸酐 、 环己硫醇 在 dihydroquinine-derived chiral catalyst 作用下， 以 various solvent(s) 为溶剂， 反应 48.0h， 生成 (3R)-5-cyclohexylsulfanyl-3-methyl-5-oxopentanoic acid 、
  参考文献：
  名称：

  Organocatalytic Asymmetric Addition of Alcohols and Thiols to Activated Electrophiles: Efficient Dynamic Kinetic Resolution and Desymmetrization Protocols

  摘要：

  [GRAPHICS]Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile. The optimum catalyst is remarkably insensitive to the steric bulk of the amino acid residue, allowing alanine, methionine, and phenylalanine-derived azalactones to undergo DKR with unprecedented levels of enantio selectivity using a synthetic catalyst. The first DKR of these substrates by thiols and the highly enantioselective desymmetrization of a meso-glutaric anhydride by thiolysis are also reported.

  DOI：

  10.1021/jo801158g

文献信息

• Organocatalytic Asymmetric Addition of Alcohols and Thiols to Activated Electrophiles: Efficient Dynamic Kinetic Resolution and Desymmetrization Protocols
  作者：Aldo Peschiulli、Cormac Quigley、Seán Tallon、Yuri K. Gun’ko、Stephen J. Connon

  DOI：10.1021/jo801158g

  日期：2008.8.1

  [GRAPHICS]Bifunctional urea-based cinchona alkaloid derivatives have been shown to promote highly efficient DKR reactions of azalactones using an alcohol nucleophile. The optimum catalyst is remarkably insensitive to the steric bulk of the amino acid residue, allowing alanine, methionine, and phenylalanine-derived azalactones to undergo DKR with unprecedented levels of enantio selectivity using a synthetic catalyst. The first DKR of these substrates by thiols and the highly enantioselective desymmetrization of a meso-glutaric anhydride by thiolysis are also reported.