(E)-3-Decen-1-yl tert-butyldimethylsilyl ether | 150667-85-9

• 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: (E)-3-Decen-1-yl tert-butyldimethylsilyl ether
• 英文别名: (E)-1-(tert-butyldimethylsilyloxy)-3-decene；(E)-1-t-butyldimethylsilyloxy-3-decene；tert-butyl-[(E)-dec-3-enoxy]-dimethylsilane
• CAS: 150667-85-9
• 化学式: C₁₆H₃₄OSi
• 分子量: 270.531
• InChiKey: ZTDPDYWJQUCXNW-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-Decen-1-yl tert-butyldimethylsilyl ether 在 四氧化锇 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 27.0h， 生成 (3S*,4S*)-1-t-butyldimethylsilyloxy-3,4-isopropylidenedioxydecane
  参考文献：
  名称：

  Mori, K.; Abe, K., Polish Journal of Chemistry, 1994, vol. 68, # 11, p. 2255 - 2264

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Decyn-1-yl tert-butyldimethylsilyl ether 在 氨 、 sodium 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到(E)-3-Decen-1-yl tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Metal/ammonia reduction of ethers of 3-decyn-1-ol: effects of structure and conditions on cleavage and rearrangement

  摘要：

  Reduction of the THP, ethyl, tert-butyl and tert-butyldimethylsilyl (TBDMS) ethers of 3-decyn-1-ol with sodium in ammonia/THF results in extensive hydrogenolysis of the carbon-oxygen bond and concomitant bond migration, producing a mixture of 2- and 3-decenes and a very low yield of the desired (E)-homoallylic ether. Reduction in the presence of 2-methyl-2-propanol led to excellent yields of the desired (E)-3-decenol ethers. The 4- and 5-decyn-1-ol ethers were reduced normally to the (E)-decen-1-ol ethers except in the case of the TBDMS ethers which were cleaved to the (E)-alcohols under some of the reaction conditions.

  DOI：

  10.1021/jo00071a014

文献信息

• Mori, Kenji; Abe, Kaoru, Liebigs Annalen, 1995, # 6, p. 943 - 948
  作者：Mori, Kenji、Abe, Kaoru

  DOI：——

  日期：——
• Metal/ammonia reduction of ethers of 3-decyn-1-ol: effects of structure and conditions on cleavage and rearrangement
  作者：Robert E. Doolittle、Delrea G. Patrick、Robert H. Heath

  DOI：10.1021/jo00071a014

  日期：1993.9

  Reduction of the THP, ethyl, tert-butyl and tert-butyldimethylsilyl (TBDMS) ethers of 3-decyn-1-ol with sodium in ammonia/THF results in extensive hydrogenolysis of the carbon-oxygen bond and concomitant bond migration, producing a mixture of 2- and 3-decenes and a very low yield of the desired (E)-homoallylic ether. Reduction in the presence of 2-methyl-2-propanol led to excellent yields of the desired (E)-3-decenol ethers. The 4- and 5-decyn-1-ol ethers were reduced normally to the (E)-decen-1-ol ethers except in the case of the TBDMS ethers which were cleaved to the (E)-alcohols under some of the reaction conditions.
• Mori, K.; Abe, K., Polish Journal of Chemistry, 1994, vol. 68, # 11, p. 2255 - 2264
  作者：Mori, K.、Abe, K.

  DOI：——

  日期：——