Hydroxy-acetic acid (4E,6E)-(1S,2S)-1,2,4-trimethyl-3-oxo-7-phenyl-hepta-4,6-dienyl ester | 139631-00-8

• 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: Hydroxy-acetic acid (4E,6E)-(1S,2S)-1,2,4-trimethyl-3-oxo-7-phenyl-hepta-4,6-dienyl ester
• 英文别名: [(2S,3S,5E,7E)-3,5-dimethyl-4-oxo-8-phenylocta-5,7-dien-2-yl] 2-hydroxyacetate
• CAS: 139631-00-8
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: PXEKHSKMLUETFY-VMLMDLBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Hydroxy-acetic acid (4E,6E)-(1S,2S)-1,2,4-trimethyl-3-oxo-7-phenyl-hepta-4,6-dienyl ester 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 Hydroxy-acetic acid (4E,6E)-(1S,2R,3S)-3-hydroxy-1,2,4-trimethyl-7-phenyl-hepta-4,6-dienyl ester 、 Hydroxy-acetic acid (4E,6E)-(1S,2R,3R)-3-hydroxy-1,2,4-trimethyl-7-phenyl-hepta-4,6-dienyl ester
  参考文献：
  名称：

  Synthesis of the lower subunit of rhizoxin

  摘要：

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.

  DOI：

  10.1021/jo00034a010
• 作为产物：
  描述：

  ethyl (2S,3S)-3-((tert-butyldimethylsilyl)oxy)-2-methylbutanoate 在 sodium hydride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Hydroxy-acetic acid (4E,6E)-(1S,2S)-1,2,4-trimethyl-3-oxo-7-phenyl-hepta-4,6-dienyl ester
  参考文献：
  名称：

  Synthesis of the lower subunit of rhizoxin

  摘要：

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.

  DOI：

  10.1021/jo00034a010