反式-3-(甲氧羰基)-1,4-二苯基-2-氮杂环丁酮 | 103111-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 反式-3-(甲氧羰基)-1,4-二苯基-2-氮杂环丁酮
• 英文名称: methyl trans-2-oxo-1,4-diphenylazetidine-3-carboxylate
• 英文别名: trans-3-(Methoxycarbonyl)-1,4-diphenyl-2-azetidinone；trans-1,4-diphenyl-3-methoxycarbonyl-2-azetidinone；methyl (3R,4S)-2-oxo-1,4-diphenylazetidine-3-carboxylate
• CAS: 103111-96-2
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: XFKIDNUCKKOETN-HUUCEWRRSA-N

物化性质

• 沸点：
  487.4±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  反式-3-(甲氧羰基)-1,4-二苯基-2-氮杂环丁酮 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.08h， 生成 trans-1,4-diphenyl-3-acetoxymethyl-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
• 作为产物：
  描述：

  3,3-dichloro-1,4-diphenylazetidin-2-one 在 盐酸 、 高氯酸四乙基铵 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 反式-3-(甲氧羰基)-1,4-二苯基-2-氮杂环丁酮
  参考文献：
  名称：

  Casadei, Maria Antonietta; Moracci, Franco Micheletti; Inesi, Achille, Journal of the Chemical Society. Perkin transactions II, 1986, p. 419 - 424

  摘要：

  DOI：

文献信息

• Palladium-catalysed intramolecular carbenoid insertion of α-diazo-α-(methoxycarbonyl)acetanilides for oxindole synthesis
  作者：Daniel Solé、Ferran Pérez-Janer、Israel Fernández

  DOI：10.1039/c7cc00718c

  日期：——

  A novel, selective palladium-catalysed carbenoid C(aryl)-H insertion of [small alpha]-diazo-[small alpha]-(methoxycarbonyl)acetanilides leading to oxindoles is described.

  描述了新颖的，选择性的钯催化的生成的小α-重氮-[小α]-（甲氧羰基）乙酰胺的钯催化类胡萝卜素C（芳基）-H插入。
• Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives
  作者：Masahiro Miura、Masahiro Enna、Kazumi Okuro、Masakatsu Nomura

  DOI：10.1021/jo00121a018

  日期：1995.8

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.