(E)-7-Benzyloxy-4,4-dimethyl-hept-5-en-2-ol | 160509-04-6

• 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: (E)-7-Benzyloxy-4,4-dimethyl-hept-5-en-2-ol
• 英文别名: (E)-4,4-dimethyl-7-phenylmethoxyhept-5-en-2-ol
• CAS: 160509-04-6
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: FGZZDOFZTGMKCZ-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-7-Benzyloxy-4,4-dimethyl-hept-5-en-2-ol 在 potassium dioxotetrahydroxoosmate(VI) 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以56%的产率得到(2S,3S)-1-Benzyloxy-4,4-dimethyl-heptane-2,3,6-triol
  参考文献：
  名称：

  Intramolecular C-H Insertion by an Alkylidene Carbene: Diastereoselective Synthesis of a Taxol A Ring Synthon

  摘要：

  The first stage in a proposed total synthesis of the clinically effective anticancer agent taxol 1 is reported. A key step in this synthesis is the development of a new procedure for the generation and cyclization of the alkylidene carbene derived from ketone 9, to give cyclopentene 10 (formation of three new carbon-carbon bonds) in 72% yield. Ozonolysis of 10 followed by aldol condensation furnished the crystalline cyclohexenone 4.

  DOI：

  10.1021/jo00099a035
• 作为产物：
  描述：

  (E)-4,4-Dimethyl-7-(phenylmethoxy)-5-hepten-2-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以91%的产率得到(E)-7-Benzyloxy-4,4-dimethyl-hept-5-en-2-ol
  参考文献：
  名称：

  Intramolecular C-H Insertion by an Alkylidene Carbene: Diastereoselective Synthesis of a Taxol A Ring Synthon

  摘要：

  The first stage in a proposed total synthesis of the clinically effective anticancer agent taxol 1 is reported. A key step in this synthesis is the development of a new procedure for the generation and cyclization of the alkylidene carbene derived from ketone 9, to give cyclopentene 10 (formation of three new carbon-carbon bonds) in 72% yield. Ozonolysis of 10 followed by aldol condensation furnished the crystalline cyclohexenone 4.

  DOI：

  10.1021/jo00099a035

文献信息

• Intramolecular C-H Insertion by an Alkylidene Carbene: Diastereoselective Synthesis of a Taxol A Ring Synthon
  作者：Douglass F. Taber、Rainer Walter、Robert P. Meagley

  DOI：10.1021/jo00099a035

  日期：1994.10

  The first stage in a proposed total synthesis of the clinically effective anticancer agent taxol 1 is reported. A key step in this synthesis is the development of a new procedure for the generation and cyclization of the alkylidene carbene derived from ketone 9, to give cyclopentene 10 (formation of three new carbon-carbon bonds) in 72% yield. Ozonolysis of 10 followed by aldol condensation furnished the crystalline cyclohexenone 4.