4t-(3-nitro-phenyl)-2-oxo-but-3-enoic acid methyl ester | 1772-77-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4t-(3-nitro-phenyl)-2-oxo-but-3-enoic acid methyl ester
• 英文别名: 4t-(3-Nitro-phenyl)-2-oxo-but-3-ensaeure-methylester；methyl (E)-4-(3-nitrophenyl)-2-oxobut-3-enoate
• CAS: 1772-77-6
• 化学式: C₁₁H₉NO₅
• 分子量: 235.196
• InChiKey: YYILZDQKEWBZNY-AATRIKPKSA-N

物化性质

• 沸点：
  382.1±42.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮乙酸乙酯 、 4t-(3-nitro-phenyl)-2-oxo-but-3-enoic acid methyl ester 、 二苄胺 在 4-二甲氨基吡啶 、 meso-tetraphenylporphyrin iron(III) chloride 作用下， 以 氯仿 为溶剂， 以54%的产率得到
  参考文献：
  名称：

  Iron Porphyrin-Catalyzed Three-Component Reaction of Ethyl Diazoacetate with Aliphatic Amines and β,γ-Unsaturated α-Keto Esters

  摘要：

  An iron porphyrin-catalyzed three-component reaction of ethyl diazoacetate with aliphatic amines and beta,gamma-unsaturated alpha-keto esters is reported. The use of iron porphyrin catalyst allows aliphatic amines to be used as the substrate without encountering catalyst poisoning issue and a series of beta-hydroxy-alpha-amino esters are produced in high yields with excellent regioselectivities.

  DOI：

  10.1021/ol403011r
• 作为产物：
  描述：

  甲醇 、 (E)-4-(3-nitrophenyl)-2-oxo-3-butenoic acid 在 phospho-tungstic acid 、 phosphotungstic acid 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以68%的产率得到4t-(3-nitro-phenyl)-2-oxo-but-3-enoic acid methyl ester
  参考文献：
  名称：

  Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: effect of substrate structure and mechanism

  摘要：

  Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl alpha-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted alpha-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.104

文献信息

• Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: effect of substrate structure and mechanism
  作者：B. Baskar、N.G. Pandian、K. Priya、Anju Chadha

  DOI：10.1016/j.tet.2005.09.104

  日期：2005.12

  Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl alpha-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted alpha-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion. (c) 2005 Elsevier Ltd. All rights reserved.
• Iron Porphyrin-Catalyzed Three-Component Reaction of Ethyl Diazoacetate with Aliphatic Amines and β,γ-Unsaturated α-Keto Esters
  作者：Chaoqun Ma、Dong Xing、Changwei Zhai、Jiuwei Che、Shunying Liu、Jue Wang、Wenhao Hu

  DOI：10.1021/ol403011r

  日期：2013.12.20

  An iron porphyrin-catalyzed three-component reaction of ethyl diazoacetate with aliphatic amines and beta,gamma-unsaturated alpha-keto esters is reported. The use of iron porphyrin catalyst allows aliphatic amines to be used as the substrate without encountering catalyst poisoning issue and a series of beta-hydroxy-alpha-amino esters are produced in high yields with excellent regioselectivities.