2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole | 540497-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole
• CAS: 540497-05-0
• 化学式: C₁₅H₁₂BrNO₂
• 分子量: 318.17
• InChiKey: VQRIVQFHSMLWTA-UHFFFAOYSA-N

物化性质

• 沸点：
  399.5±37.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氰化钠 、 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以100%的产率得到2-(4-(benzo[d]oxazol-2-yl)-2-methoxyphenyl)acetonitrile
  参考文献：
  名称：

  Discovery of novel modulators of metabotropic glutamate receptor subtype-5

  摘要：

  A series of potent and selective mGluR5 antagonists were synthesized and evaluated in vitro and in vivo. It was found that a pyridyl functionality is a potential replacement for acetonitrile in the lead structure, with 2-pyridyl being most favored. Additionally, the benzoxazole moiety could also be replaced by other heterobicyclic rings such as imidazothiazole. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.021
• 作为产物：
  描述：

  3-甲氧基-4-甲基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 甲苯 为溶剂， 反应 3.0h， 生成 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole
  参考文献：
  名称：

  Discovery of novel modulators of metabotropic glutamate receptor subtype-5

  摘要：

  A series of potent and selective mGluR5 antagonists were synthesized and evaluated in vitro and in vivo. It was found that a pyridyl functionality is a potential replacement for acetonitrile in the lead structure, with 2-pyridyl being most favored. Additionally, the benzoxazole moiety could also be replaced by other heterobicyclic rings such as imidazothiazole. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.021

文献信息

• Metabotropic glutamate receptor-5 modulators
  申请人：Arruda Jeannie

  公开号：US20050065340A1

  公开（公告）日：2005-03-24

  Phenyl compounds substituted at the 1-position with a fused bicyclo moeity formed from a five-membered heterocycle fused to a six-membered carbocycle, to a six-membered aryl, or to a six-membered hetaryl, and further optionally substituted at 2 the 3,4 positions, are mGluR5 modulators useful in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, and panic, as well as in the treatment of pain and other diseases.

  1-位置上带有融合的双环基团的苯基化合物，该融合基团由一个融合到一个六元环碳环的五元杂环形成，或者融合到一个六元芳基或六元杂芳基上，进一步可选择地在2、3、4位置上进行取代，是mGluR5调节剂，可用于治疗精神和情绪障碍，例如精神分裂症、焦虑、抑郁和恐慌，以及用于治疗疼痛和其他疾病。
• METABOTROPIC GLUTAMATE RECEPTOR-5 MODULATORS
  申请人：Merck & Co., Inc.

  公开号：EP1453815A1

  公开（公告）日：2004-09-08
• EP1453815A4
  申请人：——

  公开号：EP1453815A4

  公开（公告）日：2005-04-06
• US7087601B2
  申请人：——

  公开号：US7087601B2

  公开（公告）日：2006-08-08
• [EN] METABOTROPIC GLUTAMATE RECEPTOR-5 MODULATORS<br/>[FR] MODULATEURS DU RECEPTEUR METABOTROPIQUE 5 DU GLUTAMATE
  申请人：MERCK & CO INC

  公开号：WO2003048137A1

  公开（公告）日：2003-06-12

  Phenyl compounds substituted at the 1-position with a fused bicyclo moeity formed from a five-membered heterocycle fused to a six-membered carbocycle, to a six-membered aryl, or to a six-membered hetaryl, and further optionally substituted at the 3,4 positions, are mGluR5 modulators useful in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, and panic, as well as in the treatment of pain and other diseases.