4-(tert-butyldimethylsilyloxy)hex-5-en-2-ynoic acid | 1256812-02-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(tert-butyldimethylsilyloxy)hex-5-en-2-ynoic acid
• 英文别名: 4-[Tert-butyl(dimethyl)silyl]oxyhex-5-en-2-ynoic acid
• CAS: 1256812-02-8
• 化学式: C₁₂H₂₀O₃Si
• 分子量: 240.374
• InChiKey: BNISERXCUSRFPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(tert-butyldimethylsilyloxy)hex-5-en-2-ynoic acid 、 4-(tert-butyldimethylsilyloxy)-5-(2-ethynyl-3-methoxy-5-methylphenyl)pent-2-yn-1-ol 在 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到4-(tert-butyldimethylsilyloxy)-5-(2-ethynyl-3-methoxy-5-methylphenyl)pent-2-ynyl 4-(tert-butyldimethylsilyloxy)hex-5-en-2-ynoate
  参考文献：
  名称：

  Synthesis of the Landomycinone Skeleton

  摘要：

  The synthesis of the highly functionalized tetracyclic skeleton of landomycinone (2), the aglycon of landomycins, was performed using two pivotal steps relying on metal-catalyzed reactions. They are (1) a [2 + 2 + 2] cycloaddition of alkynes promoted by Wilkinson's catalyst to build rings B and C concomitantly and (2) a ring-closing metathesis followed by aromatization to build ring D.

  DOI：

  10.1021/jo1018377
• 作为产物：
  描述：

  二氧化碳 、 3-(tert-butyldimethylsiloxy)-4-penten-1-yne 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以99%的产率得到4-(tert-butyldimethylsilyloxy)hex-5-en-2-ynoic acid
  参考文献：
  名称：

  Synthesis of the Landomycinone Skeleton

  摘要：

  The synthesis of the highly functionalized tetracyclic skeleton of landomycinone (2), the aglycon of landomycins, was performed using two pivotal steps relying on metal-catalyzed reactions. They are (1) a [2 + 2 + 2] cycloaddition of alkynes promoted by Wilkinson's catalyst to build rings B and C concomitantly and (2) a ring-closing metathesis followed by aromatization to build ring D.

  DOI：

  10.1021/jo1018377

文献信息

• Synthesis of the Landomycinone Skeleton
  作者：Xavier Bugaut、Xavier Guinchard、Emmanuel Roulland

  DOI：10.1021/jo1018377

  日期：2010.12.3

  The synthesis of the highly functionalized tetracyclic skeleton of landomycinone (2), the aglycon of landomycins, was performed using two pivotal steps relying on metal-catalyzed reactions. They are (1) a [2 + 2 + 2] cycloaddition of alkynes promoted by Wilkinson's catalyst to build rings B and C concomitantly and (2) a ring-closing metathesis followed by aromatization to build ring D.