3-methylene-N-phenyl-4-(2-furyl)-2-azetidinone | 189621-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 3-methylene-N-phenyl-4-(2-furyl)-2-azetidinone
• 英文别名: (4R)-4-(furan-2-yl)-3-methylidene-1-phenylazetidin-2-one
• CAS: 189621-12-3
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: NJDJGFIZBONMBK-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylene-N-phenyl-4-(2-furyl)-2-azetidinone 在 palladium on activated charcoal 氢气 作用下， 生成 (3R,4R)-4-Furan-2-yl-3-methyl-1-phenyl-azetidin-2-one
  参考文献：
  名称：

  PPL-catalysed hydrolysis of 3,4-disubstituted β-lactams: Effect of chain length and stereochemistry on the enantioselectivity

  摘要：

  3,4-Disubstituted beta-lactam acetates 1a-15a have been subjected to PPL-catalysed hydrolysis. The stereochemical course of hydrolysis has been shown to depend upon the C3-C4 relative stereochemistry and the length of the chain bearing acetate functionality. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00313-5
• 作为产物：
  描述：

  (+)-cis-N-phenyl-4-(2-furyl)-3-hydroxymethyl-2-azetidinone 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-methylene-N-phenyl-4-(2-furyl)-2-azetidinone
  参考文献：
  名称：

  PPL-catalysed hydrolysis of 3,4-disubstituted β-lactams: Effect of chain length and stereochemistry on the enantioselectivity

  摘要：

  3,4-Disubstituted beta-lactam acetates 1a-15a have been subjected to PPL-catalysed hydrolysis. The stereochemical course of hydrolysis has been shown to depend upon the C3-C4 relative stereochemistry and the length of the chain bearing acetate functionality. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00313-5

文献信息

• AN ENANTIOSPECIFIC NITRONE CYCLOADDITION ROUTE TO 3-HYDROXY-2-AZETIDINONES
  作者：Amit Basak、Hassam M.M Bdour、Gautam Bhattacharya

  DOI：10.1016/s0040-4039(97)00394-8

  日期：1997.4

  4-Aryl or heteroaryl 3-methylene β-lactams 2a–2c underwenthighly stereospecific cycloaddition with various nitrones 3a–3c. The method offers an enantiospecific route to 3-hydroxy-β-lactams. © 1997 Published by Elsevier Science Ltd.

  4-芳基或杂芳基3-亚甲基β-内酰胺2a–2c与各种硝酮3a–3c进行了高度立体定向的环加成反应。该方法提供了3-羟基-β-内酰胺的对映体特异性途径。©1997由Elsevier Science Ltd发布。
• PPL-catalysed hydrolysis of 3,4-disubstituted β-lactams: Effect of chain length and stereochemistry on the enantioselectivity
  作者：Amit Basak、Gautam Bhattacharya、Hussam M.M Bdour

  DOI：10.1016/s0040-4020(98)00313-5

  日期：1998.6

  3,4-Disubstituted beta-lactam acetates 1a-15a have been subjected to PPL-catalysed hydrolysis. The stereochemical course of hydrolysis has been shown to depend upon the C3-C4 relative stereochemistry and the length of the chain bearing acetate functionality. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.