5-(tert-butyldimethylsilyl)-2-hydroxy-3-methylpenta-3,4-dienoic acid | 1342799-04-5

• 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: 5-(tert-butyldimethylsilyl)-2-hydroxy-3-methylpenta-3,4-dienoic acid
• CAS: 1342799-04-5
• 化学式: C₁₂H₂₂O₃Si
• 分子量: 242.39
• InChiKey: RGPORIXQQXYUQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsilyl)-2-hydroxy-3-methylpenta-3,4-dienoic acid 在 tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到rac-(3S,4S,Z)-5-((tert-butyldimethylsilyl)methylene)-3-hydroxy-4-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Au-catalyzed cyclization of allenylsilanes. Regioselective conversion to 2-amino-4-silylmethylene γ-butyrolactone

  摘要：

  The Au(I)-catalyzed cyclization of an allenylglycine, which possessed a silyl group attached to the opposite side of the allenic terminus, occurred at the allenic center to produce the 2-amino-4-silylmethylene-substituted gamma-butyrolactone 2a in a highly regio- and stereoselective manner. The presence of a silyl group at the allenic terminus is crucial for the present 5-endo-dig gamma-butyrolactonization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.144
• 作为产物：
  描述：

  1-[tert-butyl(dimethyl)silanyl]but-2-yn-1-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 三甲基氯硅烷 、 四丁基氟化铵 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-(tert-butyldimethylsilyl)-2-hydroxy-3-methylpenta-3,4-dienoic acid
  参考文献：
  名称：

  Au-catalyzed cyclization of allenylsilanes. Regioselective conversion to 2-amino-4-silylmethylene γ-butyrolactone

  摘要：

  The Au(I)-catalyzed cyclization of an allenylglycine, which possessed a silyl group attached to the opposite side of the allenic terminus, occurred at the allenic center to produce the 2-amino-4-silylmethylene-substituted gamma-butyrolactone 2a in a highly regio- and stereoselective manner. The presence of a silyl group at the allenic terminus is crucial for the present 5-endo-dig gamma-butyrolactonization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.144

文献信息

• Au-catalyzed cyclization of allenylsilanes. Regioselective conversion to 2-amino-4-silylmethylene γ-butyrolactone
  作者：Takuya Okada、Kazuhiko Sakaguchi、Tetsuro Shinada、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2011.07.144

  日期：2011.11

  The Au(I)-catalyzed cyclization of an allenylglycine, which possessed a silyl group attached to the opposite side of the allenic terminus, occurred at the allenic center to produce the 2-amino-4-silylmethylene-substituted gamma-butyrolactone 2a in a highly regio- and stereoselective manner. The presence of a silyl group at the allenic terminus is crucial for the present 5-endo-dig gamma-butyrolactonization. (C) 2011 Elsevier Ltd. All rights reserved.