(Z)-4-(tert-butyldimethylsilanyloxy)-4-phenylbut-2-enoic acid methyl ester | 709631-31-2

• 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: (Z)-4-(tert-butyldimethylsilanyloxy)-4-phenylbut-2-enoic acid methyl ester
• CAS: 709631-31-2
• 化学式: C₁₇H₂₆O₃Si
• 分子量: 306.477
• InChiKey: INECUQMVYCYSNW-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  甲氧羰基亚甲基三苯基正膦 、 苯乙醛,a-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]- 以 甲苯 为溶剂， 反应 0.5h， 生成 (Z)-4-(tert-butyldimethylsilanyloxy)-4-phenylbut-2-enoic acid methyl ester 、 (E)-4-(tert-butyldimethylsilanyloxy)-4-phenylbut-2-enoic acid methyl ester
  参考文献：
  名称：

  Ether-directed diastereoselectivity in catalysed Overman rearrangement: comparative studies of metal catalysts

  摘要：

  Ether-directed diastereoselectivity in Overman rearrangement of delta-methoxy and delta-TBDMSO substituted allylic trichloroacetimidates has been explored using PtCl2, PtCl4, AuCl and AuCl3 catalysts in comparison with commonly used Pd(II) catalysts. For both substrates the use of PtCl2 catalyst gave notably improved anti/syn-ratio of 1,2-aminoalcohol derivatives (anti/syn=11:1 for 5-methoxy; 6:1 for delta-TBDMSO) compared to all metal catalysts known to promote Overman rearrangement. Formation of 2-trichloromethyloxazoline was observed as a dominant side reaction in the metal catalysed rearrangement of a-methoxy substituted allylic trichloroacetimidates considerably reducing the yield of the desired product. This side reaction was suppressed when delta-TBDMS-ether was used as a directing group. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.099