(E)-12-methyltetradec-10-en-1-ol | 666704-47-8

• 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: (E)-12-methyltetradec-10-en-1-ol
• 英文别名: trans-12-Methyl-10-tetradecen-1-ol
• CAS: 666704-47-8
• 化学式: C₁₅H₃₀O
• 分子量: 226.403
• InChiKey: FPGFUNXGRLIJCY-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-12-methyltetradec-10-en-1-ol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到12-methyltetradecan-1-ol
  参考文献：
  名称：

  摘要：

  Reaction of 2-vinyltetrahydrofuran and 2-vinyltetrahydropyran with ethylmagnesium bromude in the presence ot titanium(IV) isopropoxide afforded in moderate selectivity trans-4-octen-1-ol and trans-5-nonen-1-ol respectively. Best yields and high stereochemical purity of products were obtained in ethylation under these conditions of 2-(cis-1-propenyl)tetrahydrofuran, 2-(cis-1-proprnyl)- and 2- (trans-1-propenyl) tetrahydropyran. It is assumed that the key organometallic intermediate formed was diisopropoxy-titanacycloprpopane, and direction of its addition to the doubel bond governed the streochemistry of the resulting product. The obtained trans-4-octen-1-ol and trans-7-methyl-5-nonen-1-ol were applied as initial products in the synthesis of sex pheromones of lesser plum worm (Grafolita funebrana) and tea leaf roller moth (Adoxophyes sp).

  DOI：

  10.1023/a:1026047515568
• 作为产物：
  描述：

  (E)-2-(prop-1-en-1-yl)tetrahydro-2H-pyran 在 titanium(IV) isopropylate 、 magnesium 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 3.0h， 生成 (E)-12-methyltetradec-10-en-1-ol
  参考文献：
  名称：

  摘要：

  Reaction of 2-vinyltetrahydrofuran and 2-vinyltetrahydropyran with ethylmagnesium bromude in the presence ot titanium(IV) isopropoxide afforded in moderate selectivity trans-4-octen-1-ol and trans-5-nonen-1-ol respectively. Best yields and high stereochemical purity of products were obtained in ethylation under these conditions of 2-(cis-1-propenyl)tetrahydrofuran, 2-(cis-1-proprnyl)- and 2- (trans-1-propenyl) tetrahydropyran. It is assumed that the key organometallic intermediate formed was diisopropoxy-titanacycloprpopane, and direction of its addition to the doubel bond governed the streochemistry of the resulting product. The obtained trans-4-octen-1-ol and trans-7-methyl-5-nonen-1-ol were applied as initial products in the synthesis of sex pheromones of lesser plum worm (Grafolita funebrana) and tea leaf roller moth (Adoxophyes sp).

  DOI：

  10.1023/a:1026047515568

文献信息

• ——
  作者：E. A. Matyushenkov、D. G. Churikov、N. A. Sokolov、O. G. Kulinkovich

  DOI：10.1023/a:1026047515568

  日期：——

  Reaction of 2-vinyltetrahydrofuran and 2-vinyltetrahydropyran with ethylmagnesium bromude in the presence ot titanium(IV) isopropoxide afforded in moderate selectivity trans-4-octen-1-ol and trans-5-nonen-1-ol respectively. Best yields and high stereochemical purity of products were obtained in ethylation under these conditions of 2-(cis-1-propenyl)tetrahydrofuran, 2-(cis-1-proprnyl)- and 2- (trans-1-propenyl) tetrahydropyran. It is assumed that the key organometallic intermediate formed was diisopropoxy-titanacycloprpopane, and direction of its addition to the doubel bond governed the streochemistry of the resulting product. The obtained trans-4-octen-1-ol and trans-7-methyl-5-nonen-1-ol were applied as initial products in the synthesis of sex pheromones of lesser plum worm (Grafolita funebrana) and tea leaf roller moth (Adoxophyes sp).