tert-butyl ((3R,4R)-1-benzyl-4-phenyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl)carbamate | 918307-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl ((3R,4R)-1-benzyl-4-phenyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl)carbamate
• CAS: 918307-09-2
• 化学式: C₂₄H₂₈N₂O₃
• 分子量: 392.498
• InChiKey: LZEDJMRLKMFUDE-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((3R,4R)-1-benzyl-4-phenyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl)carbamate 在 甲基磺酰胺 potassium osmate(VI) 、 potassium carbonate 、 potassium hexacyanoferrate(III) 、 sodium sulfite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以51%的产率得到tert-butyl N-[(3R,4R,5S,6R)-1-benzyl-5,6-dihydroxy-2-oxo-4-phenyl-azepan-3-yl]carbamate
  参考文献：
  名称：

  Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease

  摘要：

  A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation, of the resulting alkene. Assay of the product epoxides (10, 18, 25) and diols (9a, 17, 24) against HIV protease reveals micromolar inhibition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.009
• 作为产物：
  描述：

  (2R,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpent-4-enoic acid 在 Grubbs catalyst first generation N-甲基吡咯烷酮 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 tert-butyl ((3R,4R)-1-benzyl-4-phenyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl)carbamate
  参考文献：
  名称：

  Synthesis of amino acid derived seven-membered lactams by RCM and their evaluation against HIV protease

  摘要：

  A versatile synthesis of hydroxylated and epoxy 1-azepin 2-ones substituted at N1, C-3 and C-4 or C-7 has been developed. The sequence involves ring-closing metathesis of an amino acid derived diene amide, followed by either epoxidation or dihydroxylation, of the resulting alkene. Assay of the product epoxides (10, 18, 25) and diols (9a, 17, 24) against HIV protease reveals micromolar inhibition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.009