butyl 3-chlorodiazirine-3-carboxylate | 792950-87-9

• 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: butyl 3-chlorodiazirine-3-carboxylate
• 英文别名: 3-carbobutoxy-3-chloroaziridine
• CAS: 792950-87-9
• 化学式: C₆H₉ClN₂O₂
• 分子量: 176.603
• InChiKey: MUIMXOYBYKGJJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  51
• 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 、 butyl 3-chlorodiazirine-3-carboxylate 反应 7.0h， 以89%的产率得到butyl 1-chloro-2,2,3,3-tetramethylcyclopropanecarboxylate
  参考文献：
  名称：

  Synthesis of Carboalkoxychloro- and Bromodiazirines

  摘要：

  The first known 3H-diazirines bearing a carbonyl group and a halogen atom on C-3 have been prepared by a novel synthetic method. Carboalkoxychloro- and bromodiazirines 1a-d are formed in up to 45% yields by reductive dechlorination of carboalkoxy-N,N,N'-trichloroformamidines 9a,b using chloride or bromide ion. This method constitutes the first example of the use of N,N,N'-trichloroamidines as starting materials in organic synthesis.

  DOI：

  10.1021/jo040194r
• 作为产物：
  描述：

  carbobutoxy-N,N,N'-trichloroformamidine 在 四丁基氯化铵 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以6%的产率得到butyl 3-chlorodiazirine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Carboalkoxychloro- and Bromodiazirines

  摘要：

  The first known 3H-diazirines bearing a carbonyl group and a halogen atom on C-3 have been prepared by a novel synthetic method. Carboalkoxychloro- and bromodiazirines 1a-d are formed in up to 45% yields by reductive dechlorination of carboalkoxy-N,N,N'-trichloroformamidines 9a,b using chloride or bromide ion. This method constitutes the first example of the use of N,N,N'-trichloroamidines as starting materials in organic synthesis.

  DOI：

  10.1021/jo040194r

文献信息

• Evidence for the Cyclic CN₂ Carbene in the Gas Phase
  作者：Eva Hanzlová、Jiří Váňa、Christopher J. Shaffer、Jana Roithová、Tomáš Martinů

  DOI：10.1021/ol5027602

  日期：2014.10.17

  3-Halodiazirine-3-carboxylic acids (c-CN2XCOOH, X = Cl or Br) were prepared from their esters and converted to the corresponding sodium salts. Collision-induced dissociation (CID) of the carboxylate ions led exclusively to the loss of CO2 and the resulting c-CN2X(-) ions dissociated to c-CN2 carbene at low energies. The bond dissociation energy (BDE) for c-CN2Br(-) was found to be less than 8 kcal/mol using CID of the anion generated by electrospray ionization of the carboxylate. The analogous difluoro system (CF2XCOOH/CF2X(-)/CF2) exhibits similar dissociative behavior. All experimental BDEs are in very good agreement with MP4/aug-cc-pVTZ calculations.
• Synthesis of Carboalkoxychloro- and Bromodiazirines
  作者：Tomas Martinu、William P. Dailey

  DOI：10.1021/jo040194r

  日期：2004.10.1

  The first known 3H-diazirines bearing a carbonyl group and a halogen atom on C-3 have been prepared by a novel synthetic method. Carboalkoxychloro- and bromodiazirines 1a-d are formed in up to 45% yields by reductive dechlorination of carboalkoxy-N,N,N'-trichloroformamidines 9a,b using chloride or bromide ion. This method constitutes the first example of the use of N,N,N'-trichloroamidines as starting materials in organic synthesis.