(S)-3-Hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-5-methyl-hex-4-en-1-one | 101979-54-8

• 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: (S)-3-Hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-5-methyl-hex-4-en-1-one
• 英文别名: (3S)-3-hydroxy-5-methyl-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]hex-4-en-1-one
• CAS: 101979-54-8
• 化学式: C₁₃H₂₁NO₂S₂
• 分子量: 287.447
• InChiKey: RMAVCSAXBZBBHC-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 (R)-1-(4-异丙基-2-硫氧代噻唑啉-3-基)乙酮 在 N-乙基哌啶 、 tin(II) trifluoromethanesulfonate 作用下， 生成 (S)-3-Hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-5-methyl-hex-4-en-1-one 、 (R)-3-Hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-5-methyl-hex-4-en-1-one
  参考文献：
  名称：

  New C-4-chiral 1,3-thiazolidine-2-thiones: excellent chiral auxiliaries for highly diastereo-controlled aldol-type reactions of acetic acid and .alpha.,.beta.-unsaturated aldehydes

  摘要：

  DOI：

  10.1021/jo00362a047

文献信息

• Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione
  作者：Mathis B. Hodge、Horacio F. Olivo

  DOI：10.1016/j.tet.2004.08.008

  日期：2004.10

  The addition of chlorotitanium enolates of N-acetyl isopropyl thiazolidine-2-thione to aldehydes was investigated. The stereoselectivity of the aldol products was controlled by the number of equivalents of base added. The syn aldol product was obtained preferentially when 2 equiv of Lewis acid and 1 equiv of base were employed. The anti aldol product was obtained preferentially when 1 equiv of Lewis acid and 2 equiv of base were employed for unsaturated aldehydes. Unexpected results were found with hindered aldehydes when 2 equiv of base were employed. (C) 2004 Elsevier Ltd. All rights reserved.
• YOSHIMITSU NAGAO; YUICHI HAGIWARA; KUMAGAI TOSHIO; MASAHITO OCHIAI, J. ORG. CHEM., 51,(1986) N 12, 2391-2393
  作者：YOSHIMITSU NAGAO、 YUICHI HAGIWARA、 KUMAGAI TOSHIO、 MASAHITO OCHIAI

  DOI：——

  日期：——