3-trimethylsilylhept-1-en-4-ol | 344749-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-trimethylsilylhept-1-en-4-ol
• 英文别名: 3-triethylsilylhept-1-ene-4-ol
• CAS: 344749-95-7
• 化学式: C₁₀H₂₂OSi
• 分子量: 186.37
• InChiKey: GZUQZZPDGGSRAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  3-trimethylsilylhept-1-en-4-ol 在 palladium on activated charcoal 重铬酸吡啶 、 氢气 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、303.98 kPa 条件下， 反应 30.5h， 生成 (3R*,5R*,8aR*)-3-Butyl-5-propyloctahydroindolizine (GTX 223AB)
  参考文献：
  名称：

  Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion

  摘要：

  A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (-)-indolizidine 195B, (-)-indolizidine 223AB, (+)-monomorine and (-)-3-butyl-5-propyl indolizidine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.027
• 作为产物：
  描述：

  正丁醛 、 烯丙基三甲基硅烷 在 四甲基乙二胺 、 仲丁基锂 、 titanium(IV) isopropylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到3-trimethylsilylhept-1-en-4-ol
  参考文献：
  名称：

  Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion

  摘要：

  A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (-)-indolizidine 195B, (-)-indolizidine 223AB, (+)-monomorine and (-)-3-butyl-5-propyl indolizidine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.027

文献信息

• A convenient allylsilane-N-acyliminium route toward 5-alkylindolizidines. Diastereoselective synthesis of (±)-indolizidine 167B
  作者：Sandrine Peroche、Roland Remuson、Yvonne Gelas-Mialhe、Jean-Claude Gramain

  DOI：10.1016/s0040-4039(01)00822-x

  日期：2001.7

  A highly diastereostelective synthesis of 5-alkylindolizidines is described via an intermolecular addition of the allylsilyl functional group of homoallylic alcohols with an N-acyliminium ion derived from pyrrolidin-2-one. (C) 2001 Elsevier Science Ltd. All rights reserved.
• YAMAMOTO, YOSHINORI;YATAGAI, HIDETAKA;SAITO, YOSHIKAZU;MARUYAMA, KAZUHIRO, J. ORG. CHEM., 1984, 49, N 6, 1096-1104
  作者：YAMAMOTO, YOSHINORI、YATAGAI, HIDETAKA、SAITO, YOSHIKAZU、MARUYAMA, KAZUHIRO

  DOI：——

  日期：——
• Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion
  作者：Elisabeth Conchon、Yvonne Gelas-Mialhe、Roland Remuson

  DOI：10.1016/j.tetasy.2006.04.027

  日期：2006.4

  A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (-)-indolizidine 195B, (-)-indolizidine 223AB, (+)-monomorine and (-)-3-butyl-5-propyl indolizidine. (c) 2006 Elsevier Ltd. All rights reserved.