Hept-6-enoic acid (S)-1-acetyl-but-3-enyl ester | 252265-29-5

• 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: Hept-6-enoic acid (S)-1-acetyl-but-3-enyl ester
• 英文别名: [(3S)-2-oxohex-5-en-3-yl] hept-6-enoate
• CAS: 252265-29-5
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: UBMJRBOLUXGWRK-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Hept-6-enoic acid (S)-1-acetyl-but-3-enyl ester 在 Grubbs catalyst first generation 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (Z)-(S)-10-[(E)-1-Methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one
  参考文献：
  名称：

  Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylation

  摘要：

  An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01659-7
• 作为产物：
  描述：

  三甲基(1-甲基戊-1,4-二烯氧基)硅烷 在 4-二甲氨基吡啶 、 α-AD mix {K4[Fe(CN)6], OsO4, Na2CO3, (DHQ)2-PHAL} 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.0h， 生成 Hept-6-enoic acid (S)-1-acetyl-but-3-enyl ester
  参考文献：
  名称：

  Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylation

  摘要：

  An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01659-7