(R)-tert-butyl (2-amino-1-(2,4-dichlorophenyl)ethyl)carbamate | 1415728-54-9

• 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: (R)-tert-butyl (2-amino-1-(2,4-dichlorophenyl)ethyl)carbamate
• 英文别名: tert-butyl N-[(1R)-2-amino-1-(2,4-dichlorophenyl)ethyl]carbamate
• CAS: 1415728-54-9
• 化学式: C₁₃H₁₈Cl₂N₂O₂
• 分子量: 305.204
• InChiKey: QJZLIDLWAGTYPY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 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：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl (2-amino-1-(2,4-dichlorophenyl)ethyl)carbamate 在 ammonium acetate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 34.0h， 生成 (R)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-amine
  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 sodium tetrahydroborate 、 (1R,2R)-N¹,N²-bis[4-(1-pyrrolidinyl)-2-quinolinyl]-1,2-cyclohexanediamine 、 potassium carbonate 、 sodium sulfate 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 53.0h， 生成 (R)-tert-butyl (2-amino-1-(2,4-dichlorophenyl)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

文献信息

• Enantioselective Organocatalyzed <i>aza</i> ‐Michael Addition Reaction of 2‐Hydroxybenzophenone Imines to Nitroolefins under Batch and Flow Conditions
  作者：Andrea Guerrero‐Corella、Miguel A. Valle‐Amores、Alberto Fraile、José Alemán

  DOI：10.1002/adsc.202100635

  日期：2021.8.3

  Herein, an asymmetric organocatalytic aza-Michael addition reaction of ketimines to nitroolefins is presented. The use of 2-hydroxybenzophenone imine improves the enantioselective addition of N-centered nucleophiles to nitroalkenes by means of intramolecular hydrogen bond formation at the imine moiety. Moreover, the versatility of the process is demonstrated under both batch and flow conditions, showing

  在此，提出了酮亚胺与硝基烯烃的不对称有机催化氮杂-迈克尔加成反应。使用 2-羟基二苯甲酮亚胺通过在亚胺部分形成分子内氢键来改善N中心亲核试剂对硝基烯烃的对映选择性加成。此外，该工艺的多功能性在间歇和流动条件下都得到了证明，显示出多种硝基胺衍生物的合成，具有优异的产率和对映选择性。此外，我们将这种方法应用于 VNI 的正式合成，VNI 是一种用于治疗恰加斯病的药物样支架。
• 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.