(1R,2aR,2bR,5S,6aS)-1-[(Dimethyl-trityl-silanyl)-methyl]-6-oxo-5-phenyl-hexahydro-3-oxa-5a-aza-cyclobuta[a]pentalene-6a-carboxylic acid tert-butyl ester | 211573-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (1R,2aR,2bR,5S,6aS)-1-[(Dimethyl-trityl-silanyl)-methyl]-6-oxo-5-phenyl-hexahydro-3-oxa-5a-aza-cyclobuta[a]pentalene-6a-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (1R,2R,4R,5S,8S)-4-[[dimethyl(trityl)silyl]methyl]-6-oxo-8-phenyl-10-oxa-7-azatricyclo[5.3.0.02,5]decane-5-carboxylate
• CAS: 211573-38-5
• 化学式: C₄₁H₄₅NO₄Si
• 分子量: 643.898
• InChiKey: ORYPLNZHNCJPCS-MMTLZABZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.17
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2aR,2bR,5S,6aS)-1-[(Dimethyl-trityl-silanyl)-methyl]-6-oxo-5-phenyl-hexahydro-3-oxa-5a-aza-cyclobuta[a]pentalene-6a-carboxylic acid tert-butyl ester 在 四丁基氢氧化铵 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 以58%的产率得到(1R,2aR,2bR,5S,6aR)-1-Hydroxymethyl-6-oxo-5-phenyl-hexahydro-3-oxa-5a-aza-cyclobuta[a]pentalene-6a-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Allyldimethyltritylsilane: construction of enantiomerically pure cyclobutano[c]fused pyrrolidines

  摘要：

  Cyclobutannulation of the bicyclic lactam with allyldimethyltritylsilane is accomplished in high yield with good diastereoselectivity. The resulting tricyclic system is converted to a enantiomerically pure cyclobutane-fused pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00083-7
• 作为产物：
  描述：

  二甲基三苯甲基溴硅烷 在 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (1R,2aR,2bR,5S,6aS)-1-[(Dimethyl-trityl-silanyl)-methyl]-6-oxo-5-phenyl-hexahydro-3-oxa-5a-aza-cyclobuta[a]pentalene-6a-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Allyldimethyltritylsilane. Synthesis of Cyclopentanols, Oxetanes, and Tetrahydrofurans by Reaction with Electron Deficient Olefins

  摘要：

  Allyldimethyltritylsilane (ADTS, 1) has been employed to access a variety of cyclopentanols via Lewis acid mediated annulation to electron deficient olefins. The intermediate silylcyclopentanes were converted to their respective cyclopentanols under mild, nonepimerizing oxidative conditions. In addition, ADTS undergoes efficient annulation onto aldehydes to provide oxetanes and tetrahydrofurans. Same preliminary investigations of this annulation to chiral nonracemic bicyclic lactams are presented.

  DOI：

  10.1021/jo9805652

文献信息

• Allyldimethyltritylsilane. Synthesis of Cyclopentanols, Oxetanes, and Tetrahydrofurans by Reaction with Electron Deficient Olefins
  作者：Michael D. Groaning、Gregory P. Brengel、A. I. Meyers

  DOI：10.1021/jo9805652

  日期：1998.8.1

  Allyldimethyltritylsilane (ADTS, 1) has been employed to access a variety of cyclopentanols via Lewis acid mediated annulation to electron deficient olefins. The intermediate silylcyclopentanes were converted to their respective cyclopentanols under mild, nonepimerizing oxidative conditions. In addition, ADTS undergoes efficient annulation onto aldehydes to provide oxetanes and tetrahydrofurans. Same preliminary investigations of this annulation to chiral nonracemic bicyclic lactams are presented.
• Allyldimethyltritylsilane: construction of enantiomerically pure cyclobutano[c]fused pyrrolidines
  作者：Michael D Groaning、Gregory P Brengel、A.I Meyers

  DOI：10.1016/s0040-4020(01)00083-7

  日期：2001.3

  Cyclobutannulation of the bicyclic lactam with allyldimethyltritylsilane is accomplished in high yield with good diastereoselectivity. The resulting tricyclic system is converted to a enantiomerically pure cyclobutane-fused pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.