(3R,4E)-19-methyl-1-trimethylsilyl-4-icosen-1-yn-3-ol | 249642-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4E)-19-methyl-1-trimethylsilyl-4-icosen-1-yn-3-ol
• 英文别名: (E,3R)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-ol
• CAS: 249642-31-7
• 化学式: C₂₄H₄₆OSi
• 分子量: 378.714
• InChiKey: ISNOWHLEGPHQSC-DCCWQCMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (3R,4E)-19-methyl-1-trimethylsilyl-4-icosen-1-yn-3-ol 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (3R,4E)-19-methyl-4-icosen-1-yn-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum

  摘要：

  The first stereoselective synthesis of (3R,4E)-19-methyiicos-4-en-1-yn-3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent (E)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-one in the presence of a chiral oxazaborolidine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00251-7
• 作为产物：
  描述：

  15-methyl-1-hexadecanol 在 lithium hydroxide 、 三氯化铝 、 草酰氯 、 dimethyl sulfide borane 、 (R)-1-methyl-3,3,4-triphenyl<1,3,2>oxazaborole 、 二甲基亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 18.42h， 生成 (3R,4E)-19-methyl-1-trimethylsilyl-4-icosen-1-yn-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum

  摘要：

  The first stereoselective synthesis of (3R,4E)-19-methyiicos-4-en-1-yn-3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent (E)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-one in the presence of a chiral oxazaborolidine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00251-7

文献信息

• Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum
  作者：Jordi Garcia、Marta López、Joan Romeu

  DOI：10.1016/s0957-4166(99)00251-7

  日期：1999.7

  The first stereoselective synthesis of (3R,4E)-19-methyiicos-4-en-1-yn-3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent (E)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-one in the presence of a chiral oxazaborolidine. (C) 1999 Elsevier Science Ltd. All rights reserved.