diazoacetic acid cyanomethyl ester | 146229-19-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diazoacetic acid cyanomethyl ester
• 英文别名: cyanomethyl diazoacetate；Diazoacetic acid cyanomethyl ester；cyanomethyl 2-diazoacetate
• CAS: 146229-19-8
• 化学式: C₄H₃N₃O₂
• 分子量: 125.087
• InChiKey: PCKUPOZEGFMAGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-2-丁烯 、 diazoacetic acid cyanomethyl ester 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到2,2,3,3-tetramethylcyclopropanecarboxylic acid cyanomethyl ester
  参考文献：
  名称：

  Synthesis and carbene decomposition of functionally substituted diazoacetic acid esters. 8. Cyanomethyl diazoacetate

  摘要：

  Diazoacetic acid cyanomethyl ester (1) was synthesized, and its chemical conversions were investigated. Catalytic denitration of compound 1 with Rh2-(OAc)4 in CH2Cl2 at 25-degrees-C in the presence of alkenes, dienes-1,3, and alkynes-1 afforded the corresponding cyclopropane- and cyclopropenecarboxylic-3 acid esters in yields of 80-85% and was almost independent of the type of unsaturated acceptor. Competitive interaction methods showed that compound 1 has a high reactivity toward terminal alkenes and alkynes, which is comparable to that of methyl and propargyl diazoacetates.

  DOI：

  10.1007/bf00869513
• 作为产物：
  描述：

  aminoacetic acid cyanomethyl ester hydrochloride 在 acetate buffer 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到diazoacetic acid cyanomethyl ester
  参考文献：
  名称：

  Synthesis and carbene decomposition of functionally substituted diazoacetic acid esters. 8. Cyanomethyl diazoacetate

  摘要：

  Diazoacetic acid cyanomethyl ester (1) was synthesized, and its chemical conversions were investigated. Catalytic denitration of compound 1 with Rh2-(OAc)4 in CH2Cl2 at 25-degrees-C in the presence of alkenes, dienes-1,3, and alkynes-1 afforded the corresponding cyclopropane- and cyclopropenecarboxylic-3 acid esters in yields of 80-85% and was almost independent of the type of unsaturated acceptor. Competitive interaction methods showed that compound 1 has a high reactivity toward terminal alkenes and alkynes, which is comparable to that of methyl and propargyl diazoacetates.

  DOI：

  10.1007/bf00869513

文献信息

• Rhodium(<scp>ii</scp>)-mediated reactions of thiobenzoylketene S,N-acetals with α-diazo carbonyl compounds: synthesis of 2-substituted 3-alkylamino-5-phenylthiophenes
  作者：Hyun Min Song、Kyongtae Kim

  DOI：10.1039/b203931a

  日期：——

  Treatment of 3-methylamino-3-methylsulfanyl-1-phenylpropenethione 1 with excess (2.5 equiv.) α-diazo carbonyl compounds such as α-diazoketones and α-diazoesters in the presence of a catalytic amount of Rh(II) acetate in CH2Cl2 at rt gave 2-acyl- or 2-aroyl-3-methylamino-5-phenylthiophenes and alkyl 3-methylamino-5-phenylthiophene-2-carboxylates, respectively, as major products along with 1-phenyl-2-methylsulfanylethanones. The formation of the major products indicates that the carbenes or carbenoids generated interact initially with the thione sulfur of 1.

  3-甲基氨基-3-甲基硫醇-1-苯基丙烯硫酮1与多量（2.5倍当量）α-二氮烯羰基化合物（如α-二氮酮和α-二氮酯）在常温下的二氯甲烷中，存在催化量的铑(II)醋酸盐反应，主要生成2-酰基或2-芳酰基-3-甲基氨基-5-苯基噻吩和烷基3-甲基氨基-5-苯基噻吩-2-羧酸酯，以及1-苯基-2-甲基硫基乙酮。主要产品的形成表明，生成的卡宾或卡宾类化合物最初与1的硫酮硫发生相互作用。
• Synthesis and carbene decomposition of functionally substituted diazoacetic acid esters. 8. Cyanomethyl diazoacetate
  作者：E. A. Shapiro、A. B. Dyatkin、O. M. Nefedov

  DOI：10.1007/bf00869513

  日期：1992.2

  Diazoacetic acid cyanomethyl ester (1) was synthesized, and its chemical conversions were investigated. Catalytic denitration of compound 1 with Rh2-(OAc)4 in CH2Cl2 at 25-degrees-C in the presence of alkenes, dienes-1,3, and alkynes-1 afforded the corresponding cyclopropane- and cyclopropenecarboxylic-3 acid esters in yields of 80-85% and was almost independent of the type of unsaturated acceptor. Competitive interaction methods showed that compound 1 has a high reactivity toward terminal alkenes and alkynes, which is comparable to that of methyl and propargyl diazoacetates.