tert-butyl (3S,4S,Z)-5-((tert-butyldimethylsilyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate | 1341205-59-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (3S,4S,Z)-5-((tert-butyldimethylsilyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate
• 英文别名: tert-butyl N-[(3S,4S,5Z)-5-[[tert-butyl(dimethyl)silyl]methylidene]-4-methyl-2-oxooxolan-3-yl]carbamate
• CAS: 1341205-59-1
• 化学式: C₁₇H₃₁NO₄Si
• 分子量: 341.523
• InChiKey: YLULXTCWBKYXOP-HNCWSSJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,4S,Z)-5-((tert-butyldimethylsilyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  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：

  (2S,aS)-2-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyl)-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81%的产率得到tert-butyl (3S,4S,Z)-5-((tert-butyldimethylsilyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate
  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