(3R,7aS)-3-phenyl-3,7a-dihydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one | 241466-61-5

• 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: (3R,7aS)-3-phenyl-3,7a-dihydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 241466-61-5
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: BDCQQTOXPIEOHS-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,7aS)-3-phenyl-3,7a-dihydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1S,4S,5R)-3-[(1R)-2-hydroxy-1-phenylethyl]-4-prop-2-enyl-3-azabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  An asymmetric synthesis of the key precursor to (−)-indolizomycin

  摘要：

  Using chiral bicyclic lactams, containing an alpha,beta-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00728-5
• 作为产物：
  描述：

  (3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-B]唑-5(6H)-酮 在 苯甲砜 、 potassium hydride 作用下， 以 甲苯 为溶剂， 以85%的产率得到(3R,7aS)-3-phenyl-3,7a-dihydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one
  参考文献：
  名称：

  An asymmetric synthesis of the key precursor to (−)-indolizomycin

  摘要：

  Using chiral bicyclic lactams, containing an alpha,beta-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00728-5

文献信息

• An asymmetric synthesis of the key precursor to (−)-indolizomycin
  作者：Michael D. Groaning、A.I. Meyers

  DOI：10.1016/s0040-4039(99)00728-5

  日期：1999.6

  Using chiral bicyclic lactams, containing an alpha,beta-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.