3-氯异喹啉-4-醇 | 101774-33-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 异喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 3-氯异喹啉-4-醇
• 英文名称: 3-chloro-4-hydroxyisoquinoline
• 英文别名: 3-chloro-isoquinolin-4-ol；3-Chlor-isochinolin-4-ol；3-Chloroisoquinolin-4-OL
• CAS: 101774-33-8
• 化学式: C₉H₆ClNO
• 分子量: 179.606
• InChiKey: HLMAYSDUIAOBQE-UHFFFAOYSA-N

物化性质

• 熔点：
  168.5-169.5 °C (decomp)
• 沸点：
  425.6±25.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

反应信息

• 作为产物：
  描述：

  4-羟基异喹啉 在 Escherichia coli BL₂₁-CodonPlus (DE₃)-RIL/pJZ₅₄ 作用下， 以8.5 mg的产率得到3-氯异喹啉-4-醇
  参考文献：
  名称：

  Specific chlorination of isoquinolines by a fungal flavin-dependent halogenase

  摘要：

  Rdc2 is the first flavin-dependent halogenase identified from fungi. Based on the reported structure of the bacterial halogenase Cm1S, we have built a homology model for Rdc2. The model suggests an open substrate binding site that is capable of binding the natural substrate, monocillin II, and possibly other molecules such as 4-hydroxyisoquinoline (1) and 6-hydroxyisoquinoline (2). In vitro and in vivo halogenation experiments confirmed that 1 and 2 can be halogenated at the position ortho to the hydroxyl group, leading to the synthesis of the chlorinated isoquinolines la and 2a, respectively, which further expands the spectrum of identified substrates of Rdc2. This work revealed that Rdc2 is a useful biocatalyst for the synthesis of various halogenated compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.038

文献信息

• The Rearrangement of Isoquinoline-N-Oxides. II. Observations with N-Hydroxyisocarbostyrils and Other Substituted Derivatives¹
  作者：Michael M. Robison、Bonnie L. Robison

  DOI：10.1021/ja01546a060

  日期：1958.7
• Specific chlorination of isoquinolines by a fungal flavin-dependent halogenase
  作者：Jia Zeng、Anna K. Lytle、David Gage、Sean J. Johnson、Jixun Zhan

  DOI：10.1016/j.bmcl.2012.12.038

  日期：2013.2

  Rdc2 is the first flavin-dependent halogenase identified from fungi. Based on the reported structure of the bacterial halogenase Cm1S, we have built a homology model for Rdc2. The model suggests an open substrate binding site that is capable of binding the natural substrate, monocillin II, and possibly other molecules such as 4-hydroxyisoquinoline (1) and 6-hydroxyisoquinoline (2). In vitro and in vivo halogenation experiments confirmed that 1 and 2 can be halogenated at the position ortho to the hydroxyl group, leading to the synthesis of the chlorinated isoquinolines la and 2a, respectively, which further expands the spectrum of identified substrates of Rdc2. This work revealed that Rdc2 is a useful biocatalyst for the synthesis of various halogenated compounds. (C) 2012 Elsevier Ltd. All rights reserved.