1-(4-aminophenyl)-1,2-ethanediol | 112534-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-aminophenyl)-1,2-ethanediol
• 英文别名: 4-Amino-phenyl-aethylenglykol；1-(4-Aminophenyl)ethane-1,2-diol
• CAS: 112534-18-6
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: ANIQOFHUNWJCPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  390.2±27.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氯吲哚-2-羧酸 、 1-(4-aminophenyl)-1,2-ethanediol 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以76%的产率得到5-Chloroindolecarboxamide, 2f
  参考文献：
  名称：

  合成5-氯-N-芳基-1H-吲哚-2-羧酰胺衍生物作为人肝糖原磷酸化酶抑制剂。

  摘要：

  制备了一系列5-氯-N-芳基-1H-吲哚-2-羧酰胺衍生物，并将其评估为人肝糖原磷酸化酶α（hLGPa）的抑制剂。一种化合物5-氯-N- [4-（1,2-二羟乙基）苯基] -1H-吲哚-2-羧酰胺（2f）抑制hLGPa，IC（50）为0.90microM。2f的吡啶类似物在培养的原代肝细胞中具有胰高血糖素诱导的葡萄糖输出抑制活性，IC（50）为0.62microM，在糖尿病db / db小鼠中具有口服降血糖活性。晶体学测定2f与hLGPa的配合物显示抑制剂在二聚体界面的溶剂腔中结合，两个羟基与hLGPa形成有利的静电相互作用。

  DOI：

  10.1016/j.bmc.2008.04.010
• 作为产物：
  描述：

  4-硝基苯基-乙二醇 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以95%的产率得到1-(4-aminophenyl)-1,2-ethanediol
  参考文献：
  名称：

  Highly enantioselective deracemization of 1-phenyl-1,2-ethanediol and its derivatives by stereoinversion using Candida albicans in a one-pot process

  摘要：

  A very simple methodology was developed to transform racemic 1-(4-substitutedphenyl)-1,2-ethanediols using resting cells of Candida albicans CCT 0776 through a one-pot two-step process in which the (R)-stereoisomer was completely oxidized to the corresponding substituted-alpha-hydroxyacetophenones, which were completely reduced to produce (S)-1-(4-substitutedphenyl)-1,2-ethanediols in good isolated yield (60-85%) and with high enantiomeric excess (99% ee). The overall process corresponded to an enantioselective deracemization by stereoinversion of the (R)-enantiomer. The process was not achieved for other similar 1,2-diols using the same reaction conditions, which indicates a structural restriction of substrates by the active pocket of the enzymes of C. albicans involved in the stereoinversion process. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.08.018

文献信息

• Highly enantioselective deracemization of 1-phenyl-1,2-ethanediol and its derivatives by stereoinversion using Candida albicans in a one-pot process
  作者：Tarcila Cazetta、Paulo J.S. Moran、J. Augusto R. Rodrigues

  DOI：10.1016/j.molcatb.2014.08.018

  日期：2014.11

  A very simple methodology was developed to transform racemic 1-(4-substitutedphenyl)-1,2-ethanediols using resting cells of Candida albicans CCT 0776 through a one-pot two-step process in which the (R)-stereoisomer was completely oxidized to the corresponding substituted-alpha-hydroxyacetophenones, which were completely reduced to produce (S)-1-(4-substitutedphenyl)-1,2-ethanediols in good isolated yield (60-85%) and with high enantiomeric excess (99% ee). The overall process corresponded to an enantioselective deracemization by stereoinversion of the (R)-enantiomer. The process was not achieved for other similar 1,2-diols using the same reaction conditions, which indicates a structural restriction of substrates by the active pocket of the enzymes of C. albicans involved in the stereoinversion process. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis of 5-chloro-N-aryl-1H-indole-2-carboxamide derivatives as inhibitors of human liver glycogen phosphorylase a
  作者：Kenichi Onda、Takayuki Suzuki、Ryota Shiraki、Yasuhiro Yonetoku、Kenji Negoro、Kazuhiro Momose、Naoko Katayama、Masaya Orita、Tomohiko Yamaguchi、Mitsuaki Ohta、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2008.04.010

  日期：2008.5

  A series of 5-chloro-N-aryl-1H-indole-2-carboxamide derivatives were prepared and evaluated as inhibitors of human liver glycogen phosphorylase a (hLGPa). One compound, 5-chloro-N-[4-(1,2-dihydroxyethyl)phenyl]-1H-indole-2-carboxamide (2f), inhibited hLGPa with an IC(50) of 0.90microM. The pyridine analogue of 2f showed inhibitory activity of glucagon-induced glucose output in cultured primary hepatocytes

  制备了一系列5-氯-N-芳基-1H-吲哚-2-羧酰胺衍生物，并将其评估为人肝糖原磷酸化酶α（hLGPa）的抑制剂。一种化合物5-氯-N- [4-（1,2-二羟乙基）苯基] -1H-吲哚-2-羧酰胺（2f）抑制hLGPa，IC（50）为0.90microM。2f的吡啶类似物在培养的原代肝细胞中具有胰高血糖素诱导的葡萄糖输出抑制活性，IC（50）为0.62microM，在糖尿病db / db小鼠中具有口服降血糖活性。晶体学测定2f与hLGPa的配合物显示抑制剂在二聚体界面的溶剂腔中结合，两个羟基与hLGPa形成有利的静电相互作用。