(3S,4R,5R)-1-Allyl-3,4-bis-benzyloxy-5-vinyl-pyrrolidin-2-one | 208990-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R,5R)-1-Allyl-3,4-bis-benzyloxy-5-vinyl-pyrrolidin-2-one
• 英文别名: (3S,4R,5R)-5-ethenyl-3,4-bis(phenylmethoxy)-1-prop-2-enylpyrrolidin-2-one
• CAS: 208990-27-6
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.456
• InChiKey: AOBZOOFXJCDWEW-VSKRKVRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-1-Allyl-3,4-bis-benzyloxy-5-vinyl-pyrrolidin-2-one 在 ruthenium carbene complex 作用下， 以 苯 为溶剂， 反应 24.0h， 以66%的产率得到(1R,2S,7aR)-1,2-Bis-benzyloxy-1,2,5,7a-tetrahydro-pyrrolizin-3-one
  参考文献：
  名称：

  Ring-closing metathesis mediated synthesis of pyrrolizidine and quinolizidine azasugars

  摘要：

  The synthesis of a novel perbenzylated pyrrolizidine starting from 2,3,5-tri-O-benzyl-arabinofuranose and based on a ring-closing metathesis (RCM) reaction is presented. In an analogous procedure, 2,3,5-tri-O-benzylxylopyranose was converted into a hitherto unprecedented quinolizidine azasugar. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00635-2
• 作为产物：
  描述：

  (3S,4R,5R)-1-Allyl-3,4-bis-benzyloxy-5-hydroxymethyl-pyrrolidin-2-one 在 双(三甲基硅烷基)氨基钾 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,4R,5R)-1-Allyl-3,4-bis-benzyloxy-5-vinyl-pyrrolidin-2-one
  参考文献：
  名称：

  Ring-closing metathesis mediated synthesis of pyrrolizidine and quinolizidine azasugars

  摘要：

  The synthesis of a novel perbenzylated pyrrolizidine starting from 2,3,5-tri-O-benzyl-arabinofuranose and based on a ring-closing metathesis (RCM) reaction is presented. In an analogous procedure, 2,3,5-tri-O-benzylxylopyranose was converted into a hitherto unprecedented quinolizidine azasugar. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00635-2

文献信息

• Ring-closing metathesis mediated synthesis of pyrrolizidine and quinolizidine azasugars
  作者：Herman S. Overkleeft、Pascal Bruggeman、Upendra K. Pandit

  DOI：10.1016/s0040-4039(98)00635-2

  日期：1998.5

  The synthesis of a novel perbenzylated pyrrolizidine starting from 2,3,5-tri-O-benzyl-arabinofuranose and based on a ring-closing metathesis (RCM) reaction is presented. In an analogous procedure, 2,3,5-tri-O-benzylxylopyranose was converted into a hitherto unprecedented quinolizidine azasugar. (C) 1998 Elsevier Science Ltd. All rights reserved.