(3S,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-1-allyl-5-[(tert-butyldimethylsilyl)oxy]propargyl-2-pyrrolidinone | 270263-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-1-allyl-5-[(tert-butyldimethylsilyl)oxy]propargyl-2-pyrrolidinone
• 英文别名: (3S,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[3-[tert-butyl(dimethyl)silyl]oxyprop-1-ynyl]-1-prop-2-enylpyrrolidin-2-one
• CAS: 270263-46-2
• 化学式: C₂₈H₅₅NO₄Si₃
• 分子量: 554.005
• InChiKey: MEGSVCFSWDBBCX-SMIHKQSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-1-allyl-5-[(tert-butyldimethylsilyl)oxy]propargyl-2-pyrrolidinone 在 Grubbs catalyst first generation 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以78%的产率得到(1R,2S,7aR)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-7-[1-(tert-butyl-dimethyl-silanyloxymethyl)-vinyl]-1,2,5,7a-tetrahydro-pyrrolizin-3-one
  参考文献：
  名称：

  Creation of quaternary stereocenters by the addition of allyltributyltin to chiral cyclic N-acyliminium ions

  摘要：

  5,5-Disubstituted pyrrolidinones and 5-substituted pyrrolidinones were obtained with moderate to good diastereoisomeric excess through the cis addition of allyltributyltin and triethylsilane, respectively, to the 4-OTBS group in the N-acyliminium ion prepared from the corresponding 5-hydroxy lactams. Cyclization of an N-allyl-5-propargyl pyrrolidinone and N-allyl-5-allyl-5-substituted pyrrolidinones using Grubbs' catalyst led to the preparation of a dehydropyrre lizinone and dehydroindolizinones containing a quaternary stereocenter. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00537-6
• 作为产物：
  描述：

  3-(t-butyldimethylsilyloxy)prop-1-ynyllithium 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 (3S,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-1-allyl-5-[(tert-butyldimethylsilyl)oxy]propargyl-2-pyrrolidinone
  参考文献：
  名称：

  Creation of quaternary stereocenters by the addition of allyltributyltin to chiral cyclic N-acyliminium ions

  摘要：

  5,5-Disubstituted pyrrolidinones and 5-substituted pyrrolidinones were obtained with moderate to good diastereoisomeric excess through the cis addition of allyltributyltin and triethylsilane, respectively, to the 4-OTBS group in the N-acyliminium ion prepared from the corresponding 5-hydroxy lactams. Cyclization of an N-allyl-5-propargyl pyrrolidinone and N-allyl-5-allyl-5-substituted pyrrolidinones using Grubbs' catalyst led to the preparation of a dehydropyrre lizinone and dehydroindolizinones containing a quaternary stereocenter. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00537-6

文献信息

• Creation of quaternary stereocenters by the addition of allyltributyltin to chiral cyclic N-acyliminium ions
  作者：Cristina Maria Schuch、Ronaldo Aloise Pilli

  DOI：10.1016/s0957-4166(99)00537-6

  日期：2000.2

  5,5-Disubstituted pyrrolidinones and 5-substituted pyrrolidinones were obtained with moderate to good diastereoisomeric excess through the cis addition of allyltributyltin and triethylsilane, respectively, to the 4-OTBS group in the N-acyliminium ion prepared from the corresponding 5-hydroxy lactams. Cyclization of an N-allyl-5-propargyl pyrrolidinone and N-allyl-5-allyl-5-substituted pyrrolidinones using Grubbs' catalyst led to the preparation of a dehydropyrre lizinone and dehydroindolizinones containing a quaternary stereocenter. (C) 2000 Elsevier Science Ltd. All rights reserved.