1-chloro-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-chloro-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol
• 英文别名: 1-Chlor-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol；(+/-)-(3-Chlor-2-hydroxy-propyl)-(3-methyl-6-isopropyl-phenyl)-aether；(+/-)-3-Chlor-2-hydroxy-1-(3-methyl-6-isopropyl-phenoxy)-propan；γ-Chlor-β-oxy-α-thymoxy-propan；γ-Chlor-propylenglykol-α-thymylaether；1-Chloro-3-(5-methyl-2-propan-2-ylphenoxy)propan-2-ol；1-chloro-3-(5-methyl-2-propan-2-ylphenoxy)propan-2-ol
• 化学式: C₁₃H₁₉ClO₂
• 分子量: 242.746
• InChiKey: JXWKFBMINCQMGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (+/-)-1-chloro-3-(2-isopropyl-5-methylphenoxy)prop-2-yl acetate
  参考文献：
  名称：

  Lipase resolution of new (±)-3-aryloxy-1-halogenopropan-2-ols: Versatile building blocks for β-adrenergic receptor antagonists

  摘要：

  Using two commercial immobilized lipases Lipozyme(R) TL and Novozym(R) 435 effective kinetic resolution of several novel 3-aryloxy-1-halogenopropan-2-ols was achieved by acyl transfer reaction in organic solvents, yielding both enantiomers with 89-99% ee. In preparative resolutions carried out in tert-butyl methyl ether at 25 degrees C with vinyl acetate as acyl donor enantioselectivity ratio E was from 64 to 99. The resolved enantiomers were successfully used as chiral building blocks in the synthesis of new 1-alkylamino-3-aryloxypropan-2-ols, by nucleophilic halogen substitution with isopropylamine and tert-butylamine. The obtained products will be evaluated in vitro as potential new beta-adrenergic receptors antagonists. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2009.11.004
• 作为产物：
  描述：

  2-[(2-异丙基-5-甲基苯氧基)甲基]环氧乙烷 在 lithium chloride 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到1-chloro-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol
  参考文献：
  名称：

  Maciejewski; Poltorak; Kaminska, Polish Journal of Chemistry, 2009, vol. 83, # 4, p. 595 - 604

  摘要：

  DOI：

文献信息

• Marle, Journal of the Chemical Society, 1912, vol. 101, p. 309
  作者：Marle

  DOI：——

  日期：——
• Lefebvre; Levas, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 222, p. 1439
  作者：Lefebvre、Levas

  DOI：——

  日期：——
• Levas, Annales de Chimie (Cachan, France), 1948, vol. <12> 3, p. 145,191
  作者：Levas

  DOI：——

  日期：——
• The condensation of epichlorohydrin with monohydric phenols and with catechol
  作者：O. Stephenson

  DOI：10.1039/jr9540001571

  日期：——
• Lipase resolution of new (±)-3-aryloxy-1-halogenopropan-2-ols: Versatile building blocks for β-adrenergic receptor antagonists
  作者：Maciej Maciejewski、Krzysztof Półtorak、Janina E. Kamińska

  DOI：10.1016/j.molcatb.2009.11.004

  日期：2010.3

  Using two commercial immobilized lipases Lipozyme(R) TL and Novozym(R) 435 effective kinetic resolution of several novel 3-aryloxy-1-halogenopropan-2-ols was achieved by acyl transfer reaction in organic solvents, yielding both enantiomers with 89-99% ee. In preparative resolutions carried out in tert-butyl methyl ether at 25 degrees C with vinyl acetate as acyl donor enantioselectivity ratio E was from 64 to 99. The resolved enantiomers were successfully used as chiral building blocks in the synthesis of new 1-alkylamino-3-aryloxypropan-2-ols, by nucleophilic halogen substitution with isopropylamine and tert-butylamine. The obtained products will be evaluated in vitro as potential new beta-adrenergic receptors antagonists. (C) 2009 Elsevier B.V. All rights reserved.