N-(1-Cyclopropylcyclopent-1-yl)-4(S)-4-(3,4-dichlorophenyl)-4-hydroxymethylhept-6-enamide | 194427-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-Cyclopropylcyclopent-1-yl)-4(S)-4-(3,4-dichlorophenyl)-4-hydroxymethylhept-6-enamide
• 英文别名: (4S)-N-(1-cyclopropylcyclopentyl)-4-(3,4-dichlorophenyl)-4-(hydroxymethyl)hept-6-enamide
• CAS: 194427-20-8
• 化学式: C₂₂H₂₉Cl₂NO₂
• 分子量: 410.384
• InChiKey: GOSHWQUYZZFCCV-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-Cyclopropylcyclopent-1-yl)-4(S)-4-(3,4-dichlorophenyl)-4-hydroxymethylhept-6-enamide 在 二甲基硫 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 臭氧 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-1-(1-Cyclopropyl-cyclopentyl)-5-(3,4-dichloro-phenyl)-5-{2-[3-(4-fluoro-piperidin-1-yl)-azetidin-1-yl]-ethyl}-piperidin-2-one
  参考文献：
  名称：

  Structure–activity relationships of 1-alkyl-5-(3,4-dichlorophenyl)-5-{2-[3-(substituted)-1-azetidinyl]-ethyl}-2-piperidones. Part 2: Improving oral absorption

  摘要：

  A series of piperidone analogues of 1b-q, seeking replacements for the polar sulfamide moiety in clinical candidate UK-224,671- 1a, possessing reduced H-bonding potential as a strategy to improve oral absorption, were prepared. These studies led to the successful identification of In, which demonstrated equivalent pharmacology and metabolic stability to la, and greatly improved oral absorption as assessed in rat PK studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.134
• 作为产物：
  描述：

  1-cyclopropylcyclopentanol 在 lithium aluminium tetrahydride 、 sodium azide 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 生成 N-(1-Cyclopropylcyclopent-1-yl)-4(S)-4-(3,4-dichlorophenyl)-4-hydroxymethylhept-6-enamide
  参考文献：
  名称：

  Structure–activity relationships of 1-alkyl-5-(3,4-dichlorophenyl)-5-{2-[3-(substituted)-1-azetidinyl]-ethyl}-2-piperidones. Part 2: Improving oral absorption

  摘要：

  A series of piperidone analogues of 1b-q, seeking replacements for the polar sulfamide moiety in clinical candidate UK-224,671- 1a, possessing reduced H-bonding potential as a strategy to improve oral absorption, were prepared. These studies led to the successful identification of In, which demonstrated equivalent pharmacology and metabolic stability to la, and greatly improved oral absorption as assessed in rat PK studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.134