(2R,3R)-1,2-epoxy-3-dodecanol tert-butyldimethylsilyl ether | 1314116-35-2

• 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: (2R,3R)-1,2-epoxy-3-dodecanol tert-butyldimethylsilyl ether
• 英文别名: tert-butyl-dimethyl-[(1R)-1-[(2R)-oxiran-2-yl]decoxy]silane
• CAS: 1314116-35-2
• 化学式: C₁₈H₃₈O₂Si
• 分子量: 314.584
• InChiKey: IWJSKXQPTZAZMB-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,2-epoxy-3-dodecanol tert-butyldimethylsilyl ether 在 正丁基锂 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 75.0h， 生成 (9S,10R)-9,10-epoxy-nonadec-6-yne
  参考文献：
  名称：

  Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)

  摘要：

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.015
• 作为产物：
  描述：

  ethyl (2S,3R)-2,3-O-isopropylidene-dodecancarboxylate 在 咪唑 、 lithium aluminium tetrahydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.25h， 生成 (2R,3R)-1,2-epoxy-3-dodecanol tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)

  摘要：

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.015

文献信息

• Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)
  作者：David I. MaGee、Peter J. Silk、Junping Wu、Peter D. Mayo、Krista Ryall

  DOI：10.1016/j.tet.2011.05.015

  日期：2011.7

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.