1-hydroxytetradeca-7(Z),10(E)-diene trimethylsilyl ether | 188579-57-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-hydroxytetradeca-7(Z),10(E)-diene trimethylsilyl ether
• CAS: 188579-57-9
• 化学式: C₁₇H₃₄OSi
• 分子量: 282.542
• InChiKey: XHWZYCPPVRYDDW-LFOHPMNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  19.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-hydroxytetradeca-7(Z),10(E)-diene trimethylsilyl ether 在 六甲基磷酰三胺 、 三甲基氯硅烷 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 23.17h， 生成 methyl 2-methoxy-6-(pentadeca-8(Z),11(E)-dienyl)benzoate
  参考文献：
  名称：

  Synthesis of polyunsaturated constituents of phenolic lipids

  摘要：

  The diene, (ZZ)-[(8,11)-pentadecadienyl]salicylic acid, (or 2-hydroxy-6-[(ZZ)-pentadeca-8,11-dienyl]benzoic acid), has been synthesised by two routes. In the first, the key intermediate methyl or ethyl 2-hydroxy-6-(7-bromoheptyl)benzoate has been converted to methyl or ethyl 2-hydroxy-6-(10-hydroxydec-8-ynyl)benzoate and thence by reaction of the corresponding bromide with 1-pentynylmagnesium bromide to methyl or ethyl 2-hydroxy-6-(pentadeca-8,11-dienyl)benzoate. Selective reduction afforded methyl or ethyl 2-hydroxy-6-[(ZZ)-pentadeca-8,11-dienyl]benzoate. An attempt to employ the Grignard reagent from methyl 2-methoxy-6-(non-8-ynyl)benzoate and reaction with 1-bromohex-2-yne was ineffective because of a side reaction of the former with ethylmagnesium bromide to give a ketone. In the third approach ethyl 2-methoxy-6-methylbenzoate was alkylated with 1-iodotetradeca-7,10-diyne and the product selectively reduced as before to the O-methyl ether ethyl ester. A variety of C-14 intermediates has been prepared for the derivation of the 8(E), 11(E), 8(E), 11(Z) and 8(2), 11(E) stereoisomers by the alkylation procedure. A similar methodology of alkylation can be adopted for obtaining corresponding trienes in which some progress has been made commencing with the synthesis of the 8(2),11(2),14 compound. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(96)02654-0
• 作为产物：
  描述：

  6-氯-1-己醇 在 吡啶 、 盐酸 、 甲醇 、 六甲基磷酰三胺 、 diisoamyl borane 、 乙基溴化镁 、 氨 、 对甲苯磺酸 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-hydroxytetradeca-7(Z),10(E)-diene trimethylsilyl ether
  参考文献：
  名称：

  Synthesis of polyunsaturated constituents of phenolic lipids

  摘要：

  The diene, (ZZ)-[(8,11)-pentadecadienyl]salicylic acid, (or 2-hydroxy-6-[(ZZ)-pentadeca-8,11-dienyl]benzoic acid), has been synthesised by two routes. In the first, the key intermediate methyl or ethyl 2-hydroxy-6-(7-bromoheptyl)benzoate has been converted to methyl or ethyl 2-hydroxy-6-(10-hydroxydec-8-ynyl)benzoate and thence by reaction of the corresponding bromide with 1-pentynylmagnesium bromide to methyl or ethyl 2-hydroxy-6-(pentadeca-8,11-dienyl)benzoate. Selective reduction afforded methyl or ethyl 2-hydroxy-6-[(ZZ)-pentadeca-8,11-dienyl]benzoate. An attempt to employ the Grignard reagent from methyl 2-methoxy-6-(non-8-ynyl)benzoate and reaction with 1-bromohex-2-yne was ineffective because of a side reaction of the former with ethylmagnesium bromide to give a ketone. In the third approach ethyl 2-methoxy-6-methylbenzoate was alkylated with 1-iodotetradeca-7,10-diyne and the product selectively reduced as before to the O-methyl ether ethyl ester. A variety of C-14 intermediates has been prepared for the derivation of the 8(E), 11(E), 8(E), 11(Z) and 8(2), 11(E) stereoisomers by the alkylation procedure. A similar methodology of alkylation can be adopted for obtaining corresponding trienes in which some progress has been made commencing with the synthesis of the 8(2),11(2),14 compound. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(96)02654-0