(+/-)-1-(4-fluorophenyl)aziridine-2-carbonitrile | 79421-30-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+/-)-1-(4-fluorophenyl)aziridine-2-carbonitrile
• 英文别名: 1-(4-Fluorophenyl)aziridine-2-carbonitrile
• CAS: 79421-30-0
• 化学式: C₉H₇FN₂
• 分子量: 162.166
• InChiKey: MTDCRKPRTNZAEM-UHFFFAOYSA-N

物化性质

• 沸点：
  327.9±37.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(4-fluorophenyl)aziridine-2-carbonitrile 在 barium dihydroxide 、 三氟化硼乙醚 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 80.0h， 生成 2-(4-fluoroanilino)-3-(1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Apparao, S.; Singh, G.; Ila, H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 1, p. 15 - 17

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氟苯胺 在 苄基三乙基氯化铵 sodium hydroxide 、 copper diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (+/-)-1-(4-fluorophenyl)aziridine-2-carbonitrile
  参考文献：
  名称：

  Rao, S.Appa; Kumar, A.; Ila, H., Synthesis, 1981, # 8, p. 623 - 625

  摘要：

  DOI：

文献信息

• Nitrile Biotransformations for the Efficient Synthesis of Highly Enantiopure 1-Arylaziridine-2-carboxylic Acid Derivatives and Their Stereoselective Ring-Opening Reactions
  作者：Jin-Yuan Wang、De-Xian Wang、Qi-Yu Zheng、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo062339v

  日期：2007.3.1

  Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions, biotransformations of racemic 1-arylaziridine-2-carbonitriles proceeded efficiently and enantioselectively to produce highly enantiopure S-1-arylaziridine-2-carboxamides and R-1-arylaziridine-2-carboxylic acids in excellent yields. Although the nitrile hydratase exhibits no selectivity against all nitrile substrates, the amidase is highly R-enantioselective towards 1-arylaziridine-2-carboxamides. When treated with benzyl bromide, 1-phenylaziridine-2S-carboxamide underwent a highly regioselective and enantiospecific ring-opening reaction to afford an almost quantitative yield of R-beta-[(benzyl)phenylamino]-alpha-bromopropanamide (C-2 attack) and R-alpha-[(benzyl)phenylamino]-beta-bromopropanamide (C-3 attack) in a 10.5:1 ratio. Further treatment of the resulting ring-opening products with an N-nucleophilic reagent such as amine and azide led to, through most probably the aziridinium intermediate, the formation of S-alpha-substituted-beta-[(benzyl)phenylamino]propanamides in good chemical yields with high enantiomeric purity.
• RAO, S. A.;KUMAR, A.;ILA, H.;JUNJAPPA, H., SYNTHESIS, BRD, 1981, N 8, 623-625
  作者：RAO, S. A.、KUMAR, A.、ILA, H.、JUNJAPPA, H.

  DOI：——

  日期：——
• Rao, S.Appa; Kumar, A.; Ila, H., Synthesis, 1981, # 8, p. 623 - 625
  作者：Rao, S.Appa、Kumar, A.、Ila, H.、Junjappa, H.

  DOI：——

  日期：——
• Apparao, S.; Singh, G.; Ila, H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 1, p. 15 - 17
  作者：Apparao, S.、Singh, G.、Ila, H.、Junjappa, H.

  DOI：——

  日期：——