1-(4-Chlorobenzyl)piperidine-2,4-dione | 1279723-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(4-Chlorobenzyl)piperidine-2,4-dione
• 英文别名: 1-[(4-chlorophenyl)methyl]piperidine-2,4-dione
• CAS: 1279723-89-5
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: IGPKQUCMVHUFEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Chlorobenzyl)piperidine-2,4-dione 、 C₁₂H₁₇ClN₄O 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以31%的产率得到5-chloro-6-((3S)-4-(1-(4-chlorobenzyl)-2-oxopiperidin-4-yl)-3-methylpiperazin-1-yl)-N-methylnicotinamide
  参考文献：
  名称：

  II. SAR studies of pyridyl–piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists

  摘要：

  The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC(50) of 0.2 nM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.114
• 作为产物：
  描述：

  methyl 3-(N-(4-chlorobenzyl)-3-oxobutanamido)propanoate 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 21.0h， 生成 1-(4-Chlorobenzyl)piperidine-2,4-dione
  参考文献：
  名称：

  II. SAR studies of pyridyl–piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists

  摘要：

  The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC(50) of 0.2 nM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.114

文献信息

• II. SAR studies of pyridyl–piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists
  作者：Yuefei Shao、Gopinadhan N. Anilkumar、Carolyn DiIanni Carroll、Guizhen Dong、James W. Hall、Doug W. Hobbs、Yueheng Jiang、Chung-Her Jenh、Seong Heon Kim、Joseph A. Kozlowski、Brian F. McGuinness、Stuart B. Rosenblum、Inna Schulman、Neng-Yang Shih、Youheng Shu、Michael K.C. Wong、Wensheng Yu、Lisa Guise Zawacki、Qingbei Zeng

  DOI：10.1016/j.bmcl.2010.12.114

  日期：2011.3

  The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC(50) of 0.2 nM. (C) 2011 Elsevier Ltd. All rights reserved.