1-trimethylsilyl-3(E)-decen-1-yn-5-one | 261359-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-trimethylsilyl-3(E)-decen-1-yn-5-one
• CAS: 261359-07-3
• 化学式: C₁₃H₂₂OSi
• 分子量: 222.403
• InChiKey: YLWDZIWUSIYUDT-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-trimethylsilyl-3(E)-decen-1-yn-5-one 在 六甲基磷酰三胺 、 potassium fluoride 、 lithium aluminium tetrahydride 、 正丁基锂 、 乙醇 、 (S)-binaphthol 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 2.0h， 生成 13(S)-hydroxy-11(E)-octadecen-9-ynoic acid
  参考文献：
  名称：

  Novel Synthetic Approach to (S)-Coriolic Acid

  摘要：

  A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)-BINAL-H leads to the alcohol 2 (e.c.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01003-0
• 作为产物：
  描述：

  2-溴乙烯基三甲基硅烷 、 己酰氯 、 三甲基乙炔基硅 在 三氯化铝 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 以61%的产率得到1-trimethylsilyl-3(E)-decen-1-yn-5-one
  参考文献：
  名称：

  Novel Synthetic Approach to (S)-Coriolic Acid

  摘要：

  A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)-BINAL-H leads to the alcohol 2 (e.c.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01003-0

文献信息

• Novel Synthetic Approach to (S)-Coriolic Acid
  作者：Francesco Babudri、Vito Fiandanese、Giuseppe Marchese、Angela Punzi

  DOI：10.1016/s0040-4020(99)01003-0

  日期：2000.1

  A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)-BINAL-H leads to the alcohol 2 (e.c.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1. (C) 1999 Elsevier Science Ltd. All rights reserved.