(S)-1-cyclohexylpropan-2-yl (S)-1-oxohexan-2-ylcarbamate | 736144-19-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-cyclohexylpropan-2-yl (S)-1-oxohexan-2-ylcarbamate
• 英文别名: [(2S)-1-cyclohexylpropan-2-yl] N-[(2S)-1-oxohexan-2-yl]carbamate
• CAS: 736144-19-7
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: CABJFQPQQUDNAL-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-cyclohexylpropan-2-yl (S)-1-oxohexan-2-ylcarbamate 在 potassium cyanide 、 18-冠醚-6 、 羟胺 、 sodium acetate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 {(S)-1-[(tert-Butyl-dimethyl-silanyloxy)-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester
  参考文献：
  名称：

  Ketoheterocycle-based inhibitors of cathepsin K: A novel entry into the synthesis of peptidic ketoheterocycles

  摘要：

  Ketoheterocyclic inhibitors of cathepsin K have been disclosed. SAR of potency enhancing P-2-P-3 groups coupled with ketoheterocyclic warheads to provide cathepsin K inhibitors have been described. In addition, a novel route to access alpha-ketothiazoles using a key thioamide functionality has been disclosed. The mild method employed allows for the presence of diverse functional groups, such as amide and carbamate functionalities, commonly found in protease inhibitors that have peptidomimetic scaffolds. This new method should provide a quick entry into functionally diverse protease inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.091
• 作为产物：
  描述：

  (S)-(+)-1-苯基-2-丙醇 在 rhodium(III) chloride lithium hydroxide 、 sodium tetrahydroborate 、 氢气 、 三氧化硫吡啶 、 甲基三辛基氯化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 (S)-1-cyclohexylpropan-2-yl (S)-1-oxohexan-2-ylcarbamate
  参考文献：
  名称：

  Exploration of the P2–P3 SAR of aldehyde cathepsin K inhibitors

  摘要：

  The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S-2 and S-3 subsites with a series of carbamate derivatized norleucine aldehydes substituted at the P-2 and P-3 positions afforded analogs with cathepsin K IC(50)s between 600 nM and 130 pM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.084

文献信息

• Exploration of the P2–P3 SAR of aldehyde cathepsin K inhibitors
  作者：Eric E. Boros、David N. Deaton、Anne M. Hassell、Robert B. McFadyen、Aaron B. Miller、Larry R. Miller、Margot G. Paulick、Lisa M. Shewchuk、James B. Thompson、Derril H. Willard、Lois L. Wright

  DOI：10.1016/j.bmcl.2004.04.084

  日期：2004.7

  The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S-2 and S-3 subsites with a series of carbamate derivatized norleucine aldehydes substituted at the P-2 and P-3 positions afforded analogs with cathepsin K IC(50)s between 600 nM and 130 pM. (C) 2004 Elsevier Ltd. All rights reserved.
• Ketoheterocycle-based inhibitors of cathepsin K: A novel entry into the synthesis of peptidic ketoheterocycles
  作者：Francis X. Tavares、David N. Deaton、Aaron B. Miller、Larry R. Miller、Lois L. Wright

  DOI：10.1016/j.bmcl.2005.05.091

  日期：2005.9

  Ketoheterocyclic inhibitors of cathepsin K have been disclosed. SAR of potency enhancing P-2-P-3 groups coupled with ketoheterocyclic warheads to provide cathepsin K inhibitors have been described. In addition, a novel route to access alpha-ketothiazoles using a key thioamide functionality has been disclosed. The mild method employed allows for the presence of diverse functional groups, such as amide and carbamate functionalities, commonly found in protease inhibitors that have peptidomimetic scaffolds. This new method should provide a quick entry into functionally diverse protease inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.