tert-butyl N-[(2S,3S)-1-amino-3-hydroxyhexan-2-yl]carbamate | 847845-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[(2S,3S)-1-amino-3-hydroxyhexan-2-yl]carbamate
• CAS: 847845-25-4
• 化学式: C₁₁H₂₄N₂O₃
• 分子量: 232.323
• InChiKey: PXPHAMPPDOYRAB-IUCAKERBSA-N

物化性质

• 沸点：
  379.4±32.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S,3S)-1-amino-3-hydroxyhexan-2-yl]carbamate 在 sodium cyanoborohydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 {(2S,3S)-2-[2-(3-amino-5-trifluoromethyl-phenylcarbamoyl)-acetylamino]-3-hydroxyhexyl}-(2,4-dimethyl-benzyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Discovery of an orally-bioavailable CC Chemokine Receptor 2 antagonist derived from an acyclic diaminoalcohol backbone

  摘要：

  We describe an isostere-driven approach to improve upon a previously-described series of capped dipeptide antagonists of CC Chemokine Receptor 2 (CCR2). Modification of the substitution around the isostere was combined with additional changes in a distal aromatic substituent to provide single-digit nanomolar antagonists of CCR2. These studies led to the identification of 18, a compound that was suitable for studies in murine models of CCR2 activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.007
• 作为产物：
  描述：

  benzyl tert-butyl (3-(methoxy(methyl)amino)-3-oxopropane-1,2-diyl)(S)-dicarbamate 在 5%-palladium/activated carbon 、 R-alphine borane 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 168.0h， 生成 tert-butyl N-[(2S,3S)-1-amino-3-hydroxyhexan-2-yl]carbamate
  参考文献：
  名称：

  Discovery of an orally-bioavailable CC Chemokine Receptor 2 antagonist derived from an acyclic diaminoalcohol backbone

  摘要：

  We describe an isostere-driven approach to improve upon a previously-described series of capped dipeptide antagonists of CC Chemokine Receptor 2 (CCR2). Modification of the substitution around the isostere was combined with additional changes in a distal aromatic substituent to provide single-digit nanomolar antagonists of CCR2. These studies led to the identification of 18, a compound that was suitable for studies in murine models of CCR2 activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.007

文献信息

• Lactams of alkylated acyclic diamine derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050043392A1

  公开（公告）日：2005-02-24

  The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma, multiple sclerosis, artherosclerosis, and rheumatoid arthritis.

  本申请描述了式(I)的MCP-1调节剂或其药用盐形式，可用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿性关节炎。