(S)-3-(4-Indolyloxy)-1,2-propanediol | 80183-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-3-(4-Indolyloxy)-1,2-propanediol
• 英文别名: (S)-3-(4-indolyloxy)-propane-1,2-diol；3-(4-indolyloxy)-1,2-propanediol；(2S)-3-(1H-indol-4-yloxy)propane-1,2-diol
• CAS: 80183-74-0
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: FNZTVUHCYCHOFH-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-Indolyloxy)-1,2-propanediol 以50的产率得到4-(2,3-环氧丙氧基)吲哚
  参考文献：
  名称：

  Tetrahedron Asymmetry 2017, 28, 442

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(1H-吲哚-4-基氧基)-1,2-丙二醇 以99.1% ee; 的产率得到(S)-3-(4-Indolyloxy)-1,2-propanediol
  参考文献：
  名称：

  Tetrahedron Asymmetry 2017, 28, 442

  摘要：

  DOI：

文献信息

• Asymmetric Hydrolysis of (±)-1,2-Diacetoxy-3-chloropropane and Its Related Compounds with Lipase. Synthesis of Optically Pure (<i>S</i>)-Propranolol
  作者：Shinobu Iriuchijima、Natsuko Kojima

  DOI：10.1080/00021369.1982.10865218

  日期：1982.5

  Asymmetric hydrolysis of (±)-1,2-diacetoxy-3-chloropropane (1) with a very small amount of a lipoprotein lipase gave (S)-1 of 90% enantiomeric excess (e.e.). Reactions of (S)-1 with phenols in an alkaline condition yielded the corresponding (S)-3-aryloxy-1,2-propanediols. From (S)-3-(1-naphthoxy)-1,2-propanediol (5) was synthesized the optically pure (S)-isomer of propranolol [1-isopropylamino-3-(1-naphthoxy)-2-propanol] (9), one of the ²-adrenergic blocking agents. Hydrolysis of (±)-1,2-diacetoxy-3-bromopropane (11) and (±)-1,2-diacetoxyethylbenzene (12) with the lipase afforded (S)-11 of 77% e.e. and (R)-12 of 73% e.e., respectively.

  用极少量的脂蛋白脂肪酶对(±)-1,2-二乙酰氧基-3-氯丙烷（1）进行不对称水解，可得到对映体过量率为 90% 的(S)-1。在碱性条件下，(S)-1 与酚类反应生成相应的(S)-3-芳氧基-1,2-丙二醇。由(S)-3-(1-萘氧基)-1,2-丙二醇（5）合成了普萘洛尔的光学纯(S)-异构体[1-异丙基氨基-3-(1-萘氧基)-2-丙醇]（9），它是²-肾上腺素能阻断剂之一。用脂肪酶水解(±)-1,2-二乙酰氧基-3-溴丙烷(11)和(±)-1,2-二乙酰氧基乙基苯(12)，可分别得到(S)-11 和(R)-12，(S)-11 为 77%，(R)-12 为 73%。
• Phase behavior and crystal structure of 3-(1-naphthyloxy)- and 3-(4-indolyloxy)-propane-1,2-diol, synthetic precursors of chiral drugs propranolol and pindolol
  作者：Alexander A. Bredikhin、Aidar T. Gubaidullin、Zemfira A. Bredikhina、Robert R. Fayzullin、Aida I. Samigullina、Dmitry V. Zakharychev

  DOI：10.1016/j.molstruc.2013.04.018

  日期：2013.8

  Abstract Valuable precursors of popular chiral drugs propranolol and pindolol, 3-(1-naphthyloxy)-propane-1,2-diol 3 and 3-(4-indolyloxy)-propane-1,2-diol 4 were investigated by IR spectroscopy, DSC, and X-ray diffraction methods. Both compounds, crystallizing from enantiopure feed material, form “guaifenesin-like” crystal packing in which the classic H-bonded bilayers, framed in both sides by hydrophobic

  摘要 通过红外光谱研究了流行的手性药物普萘洛尔和吲哚洛尔、3-(1-萘氧基)-丙烷-1,2-二醇 3 和 3-(4-吲哚氧基)-丙烷-1,2-二醇 4 的重要前体， DSC 和 X 射线衍射方法。这两种化合物，从对映纯原料中结晶，形成“愈创甘油醚样”晶体堆积，其中经典的 H 键双层，由分子的疏水片段构成，作为基本的晶体形成基序。Diol 4 易于自发分解并保留其从外消旋体结晶的堆积模式。在相同条件下，二醇3形成弱稳定的固体外消旋化合物。确定并讨论了这种行为的一些原因。
• Synthesis and crystal structure of ( S )-pindolol
  作者：Alexander A. Bredikhin、Zemfira A. Bredikhina、Alexey V. Kurenkov、Dmitry B. Krivolapov

  DOI：10.1016/j.tetasy.2017.02.009

  日期：2017.3

  Racemic 3-(4-indolyloxy)-1,2-propanediol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic (S)-2 was converted into (S)-4-(2,3-epoxypropoxy)-1H-indole (S)-4 via a Mitsunobu reaction and then into (S)-pindolol (S)-1. The crystalline (S)-1 was studied by single crystal X-ray diffraction. A large number of symmetry independent molecules (Z' = 6) led to a weakening of the system of strong intermolecular hydrogen bonds, which combined with a loose packing (PI = 64.6%), may be the cause of the abnormally low melting point of (S)-1 as compared with rac-1. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthesis of (S)-1-(1H-indol-4-yloxy)-3-[4-(3-methoxyphenyl)-4-hydroxypiperidin-1-yl]-propan-2-ol (LY333068) succinate, and its 3-[14C]-isotopomer based on chiral glycerol-[14C] derivatives
  作者：Boris A. Czeskis

  DOI：10.1002/(sici)1099-1344(199806)41:6<465::aid-jlcr103>3.0.co;2-b

  日期：1998.6

  The 3-[C-14]-isotopomer of (S)-1-(1H-indol-4-yloxy)-3-[4-(3-methoxyphenyl)-4- hydroxypiperidin-1-yl]-propan-2-ol (LY333068), a 5HT(1A) antagonist, was prepared in 10 steps and 8.2% radiochemical yield from (L)-serine-[3-C-14]. Deamination, esterification, and protection of the resulting diet gave methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate-[3-C-14], as a chiral and radiolabeled building block, which then was subsequently coupled with 4-hydroxyindole and 4-(3-methoxyphenyl)-4-hydroxypiperidine to give the titled product with 99.4% radiochemical purity.