[(3R)-3-(Ethenyloxy)-3-phenylprop-1-yn-1-yl](trimethyl)silane | 825628-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3R)-3-(Ethenyloxy)-3-phenylprop-1-yn-1-yl](trimethyl)silane
• 英文别名: [(3R)-3-ethenoxy-3-phenylprop-1-ynyl]-trimethylsilane
• CAS: 825628-14-6
• 化学式: C₁₄H₁₈OSi
• 分子量: 230.382
• InChiKey: RMTBASFFCYUYPF-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(3R)-3-(Ethenyloxy)-3-phenylprop-1-yn-1-yl](trimethyl)silane 在 triazole 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 0.17h， 以81%的产率得到3-(trimethylsilyl)-5-phenylpenta-3,4-dien-1-ol
  参考文献：
  名称：

  1,2,3-Triazole Bound Au(I) (TA-Au) as Chemoselective Catalysts in Promoting Asymmetric Synthesis of Substituted Allenes

  摘要：

  The triazole-Au (TA-Au) complexes were identified as effective chemoselective catalysts In promoting propargyl ester/ether 3,3-rearrangements. The highly reactive allenes, which could not be isolated by simple cationic gold catalysts, were prepared in excellent yields (1% catalyst loading, > 90% yields). Unlike other reported Au catalysts, the TA-Au provided effective chirality transfer without racemization over a long period of time, giving enantioenriched allenes with excellent stereoselectivity (1% catalyst loading, up to 99% ee).

  DOI：

  10.1021/ol200714h

文献信息

• 1,2,3-Triazole Bound Au(I) (TA-Au) as Chemoselective Catalysts in Promoting Asymmetric Synthesis of Substituted Allenes
  作者：Dawei Wang、Lekh Nath S. Gautam、Cynthia Bollinger、Aleksandra Harris、Minyong Li、Xiaodong Shi

  DOI：10.1021/ol200714h

  日期：2011.5.20

  The triazole-Au (TA-Au) complexes were identified as effective chemoselective catalysts In promoting propargyl ester/ether 3,3-rearrangements. The highly reactive allenes, which could not be isolated by simple cationic gold catalysts, were prepared in excellent yields (1% catalyst loading, > 90% yields). Unlike other reported Au catalysts, the TA-Au provided effective chirality transfer without racemization over a long period of time, giving enantioenriched allenes with excellent stereoselectivity (1% catalyst loading, up to 99% ee).