(5E)-7-[(1R,2S,3R,5R)-2-(t-butyldimethylsiloxy)methyl-5-chloro-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enenitrile | 443796-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (5E)-7-[(1R,2S,3R,5R)-2-(t-butyldimethylsiloxy)methyl-5-chloro-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enenitrile
• CAS: 443796-68-7
• 化学式: C₂₄H₄₂ClNO₃Si
• 分子量: 456.141
• InChiKey: VLHHLJFUIUVQBL-YVIBLFLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  51.48
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5E)-7-[(1R,2S,3R,5R)-2-(t-butyldimethylsiloxy)methyl-5-chloro-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enenitrile 在 jones' reagent 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 (5E)-7-[(1R,2S,3R,5R)-2-(t-butyldimethylsiloxy)methyl-5-chloro-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enoic acid methyl ester
  参考文献：
  名称：

  A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues

  摘要：

  A series of 9-halo PGF analogues 1-2 and 5-13 were synthesized and biologically evaluated. Among the compounds, 2 was the best EP2-receptor agonist. A practical method of synthesizing 2 via the Julia olefination of an aldehyde 3 with an optically active sulfone 4, which was prepared by Sharpless asymmetric epoxidation of 15, was developed. Other 9-halogenated PGF analogues were synthesized essentially by the same procedure and evaluated. The absolute configuration of 16-OH of 2 was determined as S by the X-ray analysis of a salt consisting of a 1/1 molar ratio of 2 and L-lysine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00008-1
• 作为产物：
  描述：

  (3aR,4S,5R,6aS)-4-[[[(1,1-二甲基乙基)二甲基硅基]氧基]甲基]六氢-5-[(四氢-2H-吡喃-2-基)氧基]-2H-环戊并[b]呋喃-2-酮 在 2,4,6-三甲基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 四丁基氯化铵 、 三氧化硫吡啶 、 potassium carbonate 、 二甲基亚砜 、 丙酸 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 34.5h， 生成 (5E)-7-[(1R,2S,3R,5R)-2-(t-butyldimethylsiloxy)methyl-5-chloro-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]hept-5-enenitrile
  参考文献：
  名称：

  A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues

  摘要：

  A series of 9-halo PGF analogues 1-2 and 5-13 were synthesized and biologically evaluated. Among the compounds, 2 was the best EP2-receptor agonist. A practical method of synthesizing 2 via the Julia olefination of an aldehyde 3 with an optically active sulfone 4, which was prepared by Sharpless asymmetric epoxidation of 15, was developed. Other 9-halogenated PGF analogues were synthesized essentially by the same procedure and evaluated. The absolute configuration of 16-OH of 2 was determined as S by the X-ray analysis of a salt consisting of a 1/1 molar ratio of 2 and L-lysine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00008-1