(S)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpentan-1-one

• 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-thioxothiazolidin-3-yl)-5-phenylpentan-1-one
• 英文别名: (3S)-3-hydroxy-5-phenyl-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]pentan-1-one
• 化学式: C₁₇H₂₃NO₂S₂
• 分子量: 337.507
• InChiKey: GCCITODEFMNTGO-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  ethyl potassium malonate 、 (S)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpentan-1-one 在 咪唑 、 magnesium chloride 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以89%的产率得到ethyl (5S)-5-hydroxy-3-oxo-7-phenylheptanoate
  参考文献：
  名称：

  Versatile Asymmetric Synthesis of the Kavalactones:  First Synthesis of (+)-Kavain

  摘要：

  Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.

  DOI：

  10.1021/ol0493960
• 作为产物：
  描述：

  苯丙醛 、 (R)-1-(4-异丙基-2-硫氧代噻唑啉-3-基)乙酮 在 四氯化钛 、 鹰爪豆碱 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpentan-1-one 、 (S)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpentan-1-one
  参考文献：
  名称：

  Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.08.008

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.
• Versatile Asymmetric Synthesis of the Kavalactones:  First Synthesis of (+)-Kavain
  作者：Thomas E. Smith、Mabel Djang、Alan J. Velander、C. Wade Downey、Kathleen A. Carroll、Sophie van Alphen

  DOI：10.1021/ol0493960

  日期：2004.7.1

  Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.