tert-butyl ((1R)-2-bromo-1-(2,4-dichlorophenyl)-2-nitroethyl)carbamate

• 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: tert-butyl ((1R)-2-bromo-1-(2,4-dichlorophenyl)-2-nitroethyl)carbamate
• 英文别名: tert-butyl N-[(1R)-2-bromo-1-(2,4-dichlorophenyl)-2-nitroethyl]carbamate
• 化学式: C₁₃H₁₅BrCl₂N₂O₄
• 分子量: 414.083
• InChiKey: CIMINELQXXLDRF-NFJWQWPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl ((1R)-2-bromo-1-(2,4-dichlorophenyl)-2-nitroethyl)carbamate 在 sodium tetrahydroborate 、 ammonium acetate 、 cobalt(II) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 生成 (R)-tert-butyl (1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl)carbamate
  参考文献：
  名称：

  Organocatalytic, Enantioselective Synthesis of VNI: A Robust Therapeutic Development Platform for Chagas, a Neglected Tropical Disease

  摘要：

  VNI is a potent inhibitor of CYP51 and was recently shown to achieve a parasitological cure of mice infected with T. cruzi in both acute and chronic stages of infection. T. cruzi is the causative parasite of Chagas disease, a neglected tropical disease. The first enantioselective chemical synthesis of VNI (at a materials cost of less than $0.10/mg) is described. Furthermore, the key enantioselective step is performed at the 10 g scale.

  DOI：

  10.1021/ol303092v
• 作为产物：
  描述：

  tetr-butyl ((2,4-dichlorophenyl)(phenylsulfonyl)methyl)carbamate 在 (1R,2R)-N¹,N²-bis[4-(1-pyrrolidinyl)-2-quinolinyl]-1,2-cyclohexanediamine 、 potassium carbonate 、 sodium sulfate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 53.0h， 生成 tert-butyl ((1R)-2-bromo-1-(2,4-dichlorophenyl)-2-nitroethyl)carbamate
  参考文献：
  名称：

  Organocatalytic, Enantioselective Synthesis of VNI: A Robust Therapeutic Development Platform for Chagas, a Neglected Tropical Disease

  摘要：

  VNI is a potent inhibitor of CYP51 and was recently shown to achieve a parasitological cure of mice infected with T. cruzi in both acute and chronic stages of infection. T. cruzi is the causative parasite of Chagas disease, a neglected tropical disease. The first enantioselective chemical synthesis of VNI (at a materials cost of less than $0.10/mg) is described. Furthermore, the key enantioselective step is performed at the 10 g scale.

  DOI：

  10.1021/ol303092v

文献信息

• Organocatalytic, Enantioselective Synthesis of VNI: A Robust Therapeutic Development Platform for Chagas, a Neglected Tropical Disease
  作者：Mark C. Dobish、Fernando Villalta、Michael R. Waterman、Galina I. Lepesheva、Jeffrey N. Johnston

  DOI：10.1021/ol303092v

  日期：2012.12.21

  VNI is a potent inhibitor of CYP51 and was recently shown to achieve a parasitological cure of mice infected with T. cruzi in both acute and chronic stages of infection. T. cruzi is the causative parasite of Chagas disease, a neglected tropical disease. The first enantioselective chemical synthesis of VNI (at a materials cost of less than $0.10/mg) is described. Furthermore, the key enantioselective step is performed at the 10 g scale.