(R)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)-4-methylpentan-1-one | 924265-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)-4-methylpentan-1-one
• 英文别名: (3R)-3-hydroxy-4-methyl-1-[(4S)-2-sulfanylidene-4-(2,4,6-trimethylphenyl)-1,3-thiazolidin-3-yl]pentan-1-one
• CAS: 924265-95-2
• 化学式: C₁₈H₂₅NO₂S₂
• 分子量: 351.534
• InChiKey: YVDRXSZLWKMIMR-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)-4-methylpentan-1-one 生成 (R)-4-methyl-pentane-1,3-diol
  参考文献：
  名称：

  Highly Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries

  摘要：

  Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and alpha,beta-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).

  DOI：

  10.1021/ol062688b
• 作为产物：
  描述：

  (S)-4-mesitylthiazolidine-2-thione 在 四氯化钛 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-3-hydroxy-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)-4-methylpentan-1-one
  参考文献：
  名称：

  Highly Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries

  摘要：

  Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and alpha,beta-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).

  DOI：

  10.1021/ol062688b