3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester | 108604-19-9

• 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: 3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester
• 英文别名: (1S,2S)-diethyl 3-chloro-3-(4-nitrophenyl)cyclopropane-1,2-dicarboxylate；(1S,2R,3R)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester；(1R,2S,3S)-3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester
• CAS: 108604-19-9；108647-83-2；108647-84-3；111322-83-9
• 化学式: C₁₅H₁₆ClNO₆
• 分子量: 341.748
• InChiKey: REWSLTUIXFAZEZ-RYUDHWBXSA-N

物化性质

• 沸点：
  467.0±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  亚甲基,氯(4-硝基苯基)- 、 富马酸二乙酯 以 异辛烷 为溶剂， 生成 3-Chloro-3-(4-nitro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Spectroscopic detection of an arylchlorocarbene-ethyl acetate carbonyl ylide and subsequent oxirane formation

  摘要：

  Laser flash photolysis of 3-chloro-3-(p-nitrophenyl)diazirine (1) generates the corresponding ground-state singlet carbene (lambda-max = 310 nm), which reacts with ethyl acetate to form a carbonyl ylide of the ester (lambda-max = 490 nm). The absolute rate constant for ylide formation in CH2Cl2 is k = (2.85 +/- 0.17) X 10(6) M-1 s-1. Subsequent cyclization of the ylide to the corresponding oxirane (lambda-max = 350 nm) occurs with a rate constant of 1.26 x 10(6) S-1 (21-degrees-C) in ethyl acetate with Arrhenius activation parameters for oxirane formation of E(act) = 6.68 +/- 0.19 kcal/mol and log A (s-1) = 11.08 +/- 0.15. The carbonyl ylide is also intercepted with the dipolarophile, diethyl fumarate, with a rate constant of (1.04 +/- 0.07) x 10(7) M-1 s-1. Additionally, solvent polarity effects on (p-nitrophenyl)chlorocarbene reactivity and spectroscopic evidence of oxirane formation (lambda-max = 350 nm) from the related acetone ylide of (p-nitrophenyl)chlorocarbene are presented.

  DOI：

  10.1021/ja00017a033

文献信息

• Formation of a dipolar adduct in the reaction of arylchlorocarbenes with diethyl maleate
  作者：Michael P. Doyle、Kuo-Liang Loh、Lucas I. Nishioka、Michael B. McVickar、Michael T.H. Liu

  DOI：10.1016/s0040-4039(00)84961-8

  日期：1986.1