(2Z,4E)-(S)-6-Hydroxy-8-((R)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-8-oxo-octa-2,4-dienoic acid methyl ester | 185749-25-1

• 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: (2Z,4E)-(S)-6-Hydroxy-8-((R)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-8-oxo-octa-2,4-dienoic acid methyl ester
• CAS: 185749-25-1
• 化学式: C₁₅H₂₁NO₄S₂
• 分子量: 343.468
• InChiKey: CAOJUBVWCLPLSC-XZOCQMPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-(S)-6-Hydroxy-8-((R)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-8-oxo-octa-2,4-dienoic acid methyl ester 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2Z,4E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-oxo-octa-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

  摘要：

  Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02055-2
• 作为产物：
  描述：

  methyl (2Z,4E)-6-oxohexa-2,4-dienolate 、 以74%的产率得到(2Z,4E)-(S)-6-Hydroxy-8-((R)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-8-oxo-octa-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

  摘要：

  Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02055-2