dimethyl 2-(6-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-yn-3-yl)propanedioate | 1042163-35-8

• 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: dimethyl 2-(6-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-yn-3-yl)propanedioate
• CAS: 1042163-35-8
• 化学式: C₂₀H₃₆O₅Si
• 分子量: 384.588
• InChiKey: QNXBINOCWBPJML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(6-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-yn-3-yl)propanedioate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以75%的产率得到dimethyl 2-(6-hydroxy-2,6-dimethylhept-4-yn-3-yl)propanedioate
  参考文献：
  名称：

  An “Anti-Baldwin” 3-Exo-Dig Cyclization: Preparation of Vinylidene Cyclopropanes from Electron-Poor Alkenes

  摘要：

  Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an S(N)2' substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic; vinylidene cycloproparies can be prepared. These products are not available by standard carbene methodology.

  DOI：

  10.1021/ja803553a
• 作为产物：
  描述：

  2-isobutylidene malonic acid dimethyl ester 、 tert-butyldimethyl(1,1-dimethylprop-2-ynyloxy)silane 在 正丁基锂 、 氯化二乙基铝 作用下， 以 正己烷 为溶剂， 反应 3.75h， 以84%的产率得到dimethyl 2-(6-(tert-butyldimethylsilyloxy)-2,6-dimethylhept-4-yn-3-yl)propanedioate
  参考文献：
  名称：

  An “Anti-Baldwin” 3-Exo-Dig Cyclization: Preparation of Vinylidene Cyclopropanes from Electron-Poor Alkenes

  摘要：

  Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an S(N)2' substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic; vinylidene cycloproparies can be prepared. These products are not available by standard carbene methodology.

  DOI：

  10.1021/ja803553a