butyl 7-[(2R)-2-(tert-butyldimethylsilyloxymethyl)-5-thioxo-1-pyrrolidinyl]heptanoate | 1357177-78-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: butyl 7-[(2R)-2-(tert-butyldimethylsilyloxymethyl)-5-thioxo-1-pyrrolidinyl]heptanoate
• CAS: 1357177-78-6
• 化学式: C₂₂H₄₃NO₃SSi
• 分子量: 429.74
• InChiKey: WQJMENKEFXKOCK-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  28.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  butyl 7-[(2R)-2-(tert-butyldimethylsilyloxymethyl)-5-thioxo-1-pyrrolidinyl]heptanoate 在 硼烷四氢呋喃络合物 、 四丁基氟化铵 、 三氧化硫吡啶 、 sodium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 乙酸乙酯 、 甲苯 、 mineral oil 为溶剂， 反应 20.41h， 生成 7-{(2R)-2-[(1E,3S)-3-hydroxy-4-phenylbut-1-enyl]-5-thioxopyrrolidin-1-yl}heptanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists

  摘要：

  To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified gamma-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the gamma-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.009
• 作为产物：
  描述：

  在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以3.47 g的产率得到butyl 7-[(2R)-2-(tert-butyldimethylsilyloxymethyl)-5-thioxo-1-pyrrolidinyl]heptanoate
  参考文献：
  名称：

  Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists

  摘要：

  To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified gamma-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the gamma-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.009