2-(S)-hydroxy-3-(3-ethoxymethylphenyl)propan-1-ol trityl ether | 443147-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(S)-hydroxy-3-(3-ethoxymethylphenyl)propan-1-ol trityl ether
• CAS: 443147-13-5
• 化学式: C₃₁H₃₂O₃
• 分子量: 452.593
• InChiKey: OYYYGDRVNWNNGE-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(S)-hydroxy-3-(3-ethoxymethylphenyl)propan-1-ol trityl ether 在 2,4,6-三甲基吡啶 、 sodium hydroxide 、 正丁基锂 、 草酰氯 、 水 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 生成 3-(S)-hydroxy-4-(3-ethoxymethylphenyl)-1-butyne
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-phenyl-5-thiaPGE1 and 9-β-halo derivatives with improved stability

  摘要：

  To identify a new selective EP4-agonist with improved chemical stability, further chemical modification of those reported previously was continued. We focused our attention on chemical modification of the alpha chain of 3,7-dithiaPGE(1), and selected 5-thiaPGE(1), as a new chemical lead, Introduction of an optimized omega to chain to the 5-thiaPG skeleton afforded in-methoxymethyl derivative 33a, which showed the most potent EP4-receptor agonist activity and good subtype-selectivity both in vitro and in vivo. 9beta-HaloPGF derivatives were also synthesized and biologically evaluated in an attempt to block self-degradation of the beta-hydroxyketone moiety. Among these series, 39a and 39b showed potent agonist activity and good subtype-selectivity. Structure-activity relationships (SARs) are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00031-7
• 作为产物：
  描述：

  1-溴-3-(乙氧基甲基)苯 、 三苯甲基-(S)-缩水甘油醚 在 copper(l) iodide 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到2-(S)-hydroxy-3-(3-ethoxymethylphenyl)propan-1-ol trityl ether
  参考文献：
  名称：

  Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-phenyl-5-thiaPGE1 and 9-β-halo derivatives with improved stability

  摘要：

  To identify a new selective EP4-agonist with improved chemical stability, further chemical modification of those reported previously was continued. We focused our attention on chemical modification of the alpha chain of 3,7-dithiaPGE(1), and selected 5-thiaPGE(1), as a new chemical lead, Introduction of an optimized omega to chain to the 5-thiaPG skeleton afforded in-methoxymethyl derivative 33a, which showed the most potent EP4-receptor agonist activity and good subtype-selectivity both in vitro and in vivo. 9beta-HaloPGF derivatives were also synthesized and biologically evaluated in an attempt to block self-degradation of the beta-hydroxyketone moiety. Among these series, 39a and 39b showed potent agonist activity and good subtype-selectivity. Structure-activity relationships (SARs) are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00031-7