4-(3-(chloromethyl)phenyl)morpholine | 144801-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(3-(chloromethyl)phenyl)morpholine
• 英文别名: 4-[3-(Chloromethyl)phenyl]morpholine
• CAS: 144801-08-1
• 化学式: C₁₁H₁₄ClNO
• 分子量: 211.691
• InChiKey: OQBBLEIIIAHZJG-UHFFFAOYSA-N

物化性质

• 沸点：
  359.0±42.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-(chloromethyl)phenyl)morpholine 在 potassium carbonate 、 potassium iodide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 2-(6-(3-(morpholin-1-yl)benzyloxy)-2,3-dihydro-1-benzofuran-3-yl)acetic acid
  参考文献：
  名称：

  Discovery of novel pyrrole-based scaffold as potent and orally bioavailable free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

  摘要：

  The free fatty acid receptor 1 (FFA1) has gained significant interest as a novel antidiabetic target. Most of FFA1 agonists reported in the literature bearing a common biphenyl scaffold, which was crucial for toxicity verified by the researchers of Daiichi Sankyo. Herein, we describe the systematic exploration of non-biphenyl scaffold and further chemical modification of the optimal pyrrole scaffold. All of these efforts led to the identification of compound 11 as a potent and orally bioavailable FFA1 agonist without the risk of hypoglycemia. Further molecular modeling studies promoted the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.014
• 作为产物：
  描述：

  3-碘苯甲酸甲酯 在 sodium tetrahydroborate 、 copper(l) iodide 、 氯化亚砜 、 potassium carbonate 、 L-脯氨酸 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 4-(3-(chloromethyl)phenyl)morpholine
  参考文献：
  名称：

  Discovery of novel pyrrole-based scaffold as potent and orally bioavailable free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

  摘要：

  The free fatty acid receptor 1 (FFA1) has gained significant interest as a novel antidiabetic target. Most of FFA1 agonists reported in the literature bearing a common biphenyl scaffold, which was crucial for toxicity verified by the researchers of Daiichi Sankyo. Herein, we describe the systematic exploration of non-biphenyl scaffold and further chemical modification of the optimal pyrrole scaffold. All of these efforts led to the identification of compound 11 as a potent and orally bioavailable FFA1 agonist without the risk of hypoglycemia. Further molecular modeling studies promoted the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.014

文献信息

• β‐Aryl Nitrile Construction<i>via</i>Palladium‐Catalyzed Decarboxylative Benzylation of α‐Cyano Aliphatic Carboxylate Salts
  作者：Rui Shang、Zheng Huang、Xiao Xiao、Xi Lu、Yao Fu、Lei Liu

  DOI：10.1002/adsc.201200383

  日期：2012.9.17

  The palladium‐catalyzed decarboxylative benzylation of α‐cyano aliphatic carboxylate salts with benzyl electrophiles was discovered. This reaction exhibits good functional group compatibility and proceeds under relatively mild conditions. A diverse range of quaternary, tertiary and secondary β‐aryl nitriles can be conveniently prepared by this method.

  发现了α-氰基脂肪族羧酸盐与苄基亲电试剂的钯催化脱羧苄基化反应。该反应表现出良好的官能团相容性，并且在相对温和的条件下进行。通过这种方法可以方便地制备各种范围的季，叔和仲β-芳基腈。
• Pyranylphenyl hydroxyalkylnaphthoic acids as inhibitors of leukotriene biosynthesis
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0501578A1

  公开（公告）日：1992-09-02

  Compounds having the formula I: are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有式 I 的化合物： 是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和异体移植排斥反应，以及预防动脉粥样硬化斑块的形成。
• Naphthalene lactones as inhibitors of leukotriene biosynthesis
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0501579A1

  公开（公告）日：1992-09-02

  Compounds having the formula I: are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有式 I 的化合物： 是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂、 抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和异体移植排斥反应，以及预防动脉粥样硬化斑块的形成。
• [EN] BORIC ACID DERIVATIVE<br/>[FR] DÉRIVÉ D'ACIDE BORIQUE<br/>[ZH] 硼酸衍生物
  申请人：SHOUYAO HOLDINGS BEIJING CO LTD

  公开号：WO2021143924A1

  公开（公告）日：2021-07-22

  式(I)所示的硼酸衍生物或其药学上可接受的盐、溶剂化物、多晶型物或异构体，包含这些化合物的药物组合物，以及此类化合物在治疗跟lmp7相关的疾病中的用途。
• US5227399A
  申请人：——

  公开号：US5227399A

  公开（公告）日：1993-07-13