7-[(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid methyl ester | 255721-60-9

• 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: 7-[(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid methyl ester
• 英文别名: methyl 7-[(1R,2R,3R,5R)-5-chloro-2-[(E,4S)-4-(1-ethylcyclobutyl)-4-(oxan-2-yloxy)but-1-enyl]-3-(oxan-2-yloxy)cyclopentyl]heptanoate
• CAS: 255721-60-9
• 化学式: C₃₃H₅₅ClO₆
• 分子量: 583.249
• InChiKey: IQZDZGKQKFAAME-QJHYGCBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-[(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid methyl ester 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 7-{(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-cyclopentyl}-heptanoic 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：

  (3R)-1-benzenesulfonyl-3-(tetrahydro-2H-pyran-2-yl)oxy-4,4-trimethylenehexane 在 正丁基锂 、 三甲基氯硅烷 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 生成 7-[(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic 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

文献信息

• US6235780B1
  申请人：——

  公开号：US6235780B1

  公开（公告）日：2001-05-22