propan-2-yl 5-[3-[(5S)-2-oxo-5-[2-[(4R,5R)-2-oxo-5-[3-(trifluoromethyl)phenyl]-1,3-dioxolan-4-yl]ethyl]pyrrolidin-1-yl]propyl]thiophene-2-carboxylate | 1219097-68-3

• 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: propan-2-yl 5-[3-[(5S)-2-oxo-5-[2-[(4R,5R)-2-oxo-5-[3-(trifluoromethyl)phenyl]-1,3-dioxolan-4-yl]ethyl]pyrrolidin-1-yl]propyl]thiophene-2-carboxylate
• CAS: 1219097-68-3
• 化学式: C₂₇H₃₀F₃NO₆S
• 分子量: 553.6
• InChiKey: WNMXCZMUBQDQRT-XZDHIHRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  propan-2-yl 5-[3-[(5S)-2-oxo-5-[2-[(4R,5R)-2-oxo-5-[3-(trifluoromethyl)phenyl]-1,3-dioxolan-4-yl]ethyl]pyrrolidin-1-yl]propyl]thiophene-2-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 、 PF-04475270
  参考文献：
  名称：

  Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation

  摘要：

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.092
• 作为产物：
  描述：

  propan-2-yl 5-[3-[(2S)-2-[(3R,4R)-3,4-dihydroxy-4-[3-(trifluoromethyl)phenyl]butyl]-5-oxopyrrolidin-1-yl]propyl]thiophene-2-carboxylate 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成 propan-2-yl 5-[3-[(5S)-2-oxo-5-[2-[(4R,5R)-2-oxo-5-[3-(trifluoromethyl)phenyl]-1,3-dioxolan-4-yl]ethyl]pyrrolidin-1-yl]propyl]thiophene-2-carboxylate
  参考文献：
  名称：

  Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation

  摘要：

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.092