(S,S,RS)-<1-(cyclohexylmethyl)-4-oxo-2-<(tetrahydro-2H-pyran-2-yl)oxy>hexyl>carbamic acid 1,1-dimethylethyl ester | 131099-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (S,S,RS)-<1-(cyclohexylmethyl)-4-oxo-2-<(tetrahydro-2H-pyran-2-yl)oxy>hexyl>carbamic acid 1,1-dimethylethyl ester
• 英文别名: tert-butyl N-[(2S,3S)-1-cyclohexyl-3-(oxan-2-yloxy)-5-oxoheptan-2-yl]carbamate
• CAS: 131099-28-0
• 化学式: C₂₃H₄₁NO₅
• 分子量: 411.582
• InChiKey: IITQBXOSMYUUDK-AHTKWCMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S,S,RS)-<1-(cyclohexylmethyl)-4-oxo-2-<(tetrahydro-2H-pyran-2-yl)oxy>hexyl>carbamic acid 1,1-dimethylethyl ester 在 盐酸 、 钾硼氢 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 (S,S,S)-6-amino-7-cyclohexyl-3,5,-heptanediol
  参考文献：
  名称：

  氨基 1,3-二醇的合成。N-酰基活化内酰胺与碳亲核试剂的开环

  摘要：

  摘要描述了 6-氨基-7-环己基-3,5-庚二醇 1 (CDH) 和相关氨基 1,3-二醇的合成，涉及 N-酰基活化内酰胺的亲核开环。还提供了 1,3-二醇部分的立体化学证明。

  DOI：

  10.1080/00397919308013294
• 作为产物：
  描述：

  乙基溴化镁 、 (2S,3S)-2-Cyclohexylmethyl-5-oxo-3-(tetrahydro-pyran-2-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 以 四氢呋喃 为溶剂， 反应 0.5h， 以57%的产率得到(S,S,RS)-<1-(cyclohexylmethyl)-4-oxo-2-<(tetrahydro-2H-pyran-2-yl)oxy>hexyl>carbamic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors

  摘要：

  A series of renin inhibitors was synthesized that contained a 2-amino-4-thiazolyl moiety at the P2 position. These derivatives are potent inhibitors of monkey renin in vitro and are selective in that they only weakly inhibit the closely related aspartic proteinase, bovine cathepsin D. Four compounds exhibited oral blood pressure lowering activity in high-renin normotensive monkeys. One of these compounds, 22 (PD 134672), was selected for further evaluation in renal hypertensive monkeys, on the basis of its superior efficacy and duration of action in the in vitro assays and the normotensive primate model.

  DOI：

  10.1021/jm00092a006

文献信息

• Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors
  作者：William C. Patt、Harriet W. Hamilton、Michael D. Taylor、Michael J. Ryan、David G. Taylor、Cleo J. C. Connolly、Annette M. Doherty、Sylvester R. Klutchko、Ila Sircar

  DOI：10.1021/jm00092a006

  日期：1992.7

  A series of renin inhibitors was synthesized that contained a 2-amino-4-thiazolyl moiety at the P2 position. These derivatives are potent inhibitors of monkey renin in vitro and are selective in that they only weakly inhibit the closely related aspartic proteinase, bovine cathepsin D. Four compounds exhibited oral blood pressure lowering activity in high-renin normotensive monkeys. One of these compounds, 22 (PD 134672), was selected for further evaluation in renal hypertensive monkeys, on the basis of its superior efficacy and duration of action in the in vitro assays and the normotensive primate model.
• Synthesis of Amino 1,3-Diols. Ring Opening of N-Acyl Activated Lactams with Carbon Nucleophiles
  作者：S. Klutchko、J. M. Hamby、M. Reily、M. D. Taylor、J. C. Hodges

  DOI：10.1080/00397919308013294

  日期：1993.4

  Abstract A synthesis of 6-amino-7-cyclohexyl-3,5-heptanediol 1 (CDH) and related amino 1,3-diols involving a nucleophilic ring opening of N-acyl activated lactams is described. Stereochemical proof of the 1,3-diol moiety is also presented.

  摘要描述了 6-氨基-7-环己基-3,5-庚二醇 1 (CDH) 和相关氨基 1,3-二醇的合成，涉及 N-酰基活化内酰胺的亲核开环。还提供了 1,3-二醇部分的立体化学证明。