2-bromo-2-nitro-propionic acid ethyl ester | 164795-35-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-bromo-2-nitro-propionic acid ethyl ester
• 英文别名: α-Brom-α-nitro-propionsaeure-aethylester；2-Brom-2-nitro-propionsaeure-aethylester；Ethyl 2-bromo-2-nitropropanoate
• CAS: 164795-35-1
• 化学式: C₅H₈BrNO₄
• 分子量: 226.027
• InChiKey: IOKPJRRWNZRPNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-2-nitro-propionic acid ethyl ester 、 2-lithio-2-nitropropane 以 二甲基亚砜 为溶剂， 以26%的产率得到2,3-二甲基-2,3-二硝基丁烷
  参考文献：
  名称：

  Synthesis of Cαα-unsymmetrically disubstituted nitroesters by electron transfer C-alkylation of ethyl 2-nitropropionate anion

  摘要：

  The ethyl 2-nitropropionate anion was shown to react with six reductive alkylating agents to give new C-alpha alpha-unsymmctrically disubstituted nitroesters and in some cases new ethyl monosubstituted methacrylates. The C-alkylation was shown to proceed by the S(RN)1 mechanism which was confirmed by the classical criteria for S(RN)1 reaction: the electron-withdrawing group effect and classical inhibition experiments by dioxygen, p-dinitrobenzene, cupric chloride or TEMPO. For example, ethyl 2-methyl-2-nitro-3-p-nitrophenylpropionate was transformed in the corresponding amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00194-x
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 二硫化碳 、 溴 作用下， 生成 2-bromo-2-nitro-propionic acid ethyl ester
  参考文献：
  名称：

  Macbeth; Traill, Journal of the Chemical Society, 1925, vol. 127, p. 896

  摘要：

  DOI：

文献信息

• Substitution of halogen atom in ?-halonitro compounds of the aliphatic series
  作者：A. I. Yurtanov、S. K. Baidildaeva、A. N. Chekhlov、N. S. Zefirov

  DOI：10.1007/bf00717345

  日期：1994.5

  Ethyl alpha-halo-alpha-nitropropionate and -butyrate were prepared by alkylating ammonium salts of ethyl bromo- and chloronitroacetates. The addition of alkyl acrylates to alkyl chloronitroacetates or their salts gives dialkyl alpha-chloro-alpha-nitroglutarates. Sodium salts of ethyl alpha-nitro-alpha-sulfo-beta-hydroxypropionate and -butyrate were obtained by the sulfo-dehalogenation of ethyl alpha-chloro-alpha-nitro-beta-hydroxypropionate and -butyrate with sodium dithionite. Esters of a-amino acid hydrochlorides were prepared by the reduction of alkyl alpha-chloro-alpha-nitrocarboxylates. The hydrogenation of alkyl nitrosulfoacetates leads to the corresponding disodium salts of alkyl aminodisulfoacetates and piperazine-2,5-dione.