naphthalene-2-carboxylic acid (2-amino-6-hydroxy-phenyl)-amide | 883000-24-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-2-carboxylic acid (2-amino-6-hydroxy-phenyl)-amide
• 英文别名: N-(2-amino-6-hydroxyphenyl)naphthalene-2-carboxamide
• CAS: 883000-24-6
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: AMZDZMMQAMDLEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  naphthalene-2-carboxylic acid (2-amino-6-hydroxy-phenyl)-amide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到3-amino-2-[(naphthalen-2-ylmethyl)-amino]-phenol
  参考文献：
  名称：

  Regiospecific synthesis of 3-alkyl-4-hydroxybenzimidazoles as intermediates for an expedient approach to potent EP3 receptor antagonists

  摘要：

  Regiospecific construction of 3-alkyl-4-hydroxybenzimidazoles is detailed. The synthetic route involves a novel O- to N-acyl transfer reaction to address the observed exclusive O-acylation of 2-amino-3-nitrophenol starting material. This efficient route provides the targeted 3-alkyl-4-hydroxybenzimidazoles in good yields, in five steps, without the use of chromatographic purification. These key intermediates were subsequently elaborated, as shown, to provide acylsulfonamide-derived potent EP3 receptor antagonists. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.005
• 作为产物：
  描述：

  [2]naphthoic acid-(2-hydroxy-6-nitro-anilide) 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以89%的产率得到naphthalene-2-carboxylic acid (2-amino-6-hydroxy-phenyl)-amide
  参考文献：
  名称：

  Sulfonamide peri-substituted bicyclics for occlusive artery disease

  摘要：

  酰基磺酰胺，带有周取代的融合双环环化合物，用于治疗或预防前列腺素介导的疾病或症状。这些化合物的一般公式为 代表性示例是：

  公开号：

  US20060079520A1

文献信息

• Sulfonamide peri-substituted bicyclics for occlusive artery disease
  申请人：Singh Jasbir

  公开号：US20060079520A1

  公开（公告）日：2006-04-13

  Acyl sulfonamide, peri-substituted, fused bicyclic ring compounds useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed. The compounds are of the general formula A representative example is:

  酰基磺酰胺，带有周取代的融合双环环化合物，用于治疗或预防前列腺素介导的疾病或症状。这些化合物的一般公式为 代表性示例是：
• WO2006/44415
  申请人：——

  公开号：——

  公开（公告）日：——
• SULFONAMIDE PERI-SUBSTITUTED BICYCLICS FOR OCCLUSIVE ARTERY DISEASE
  申请人：DECODE GENETICS, EHF

  公开号：EP1812388B1

  公开（公告）日：2011-02-23
• Regiospecific synthesis of 3-alkyl-4-hydroxybenzimidazoles as intermediates for an expedient approach to potent EP3 receptor antagonists
  作者：Wayne Zeller、Alex S. Kiselyov、Jasbir Singh

  DOI：10.1016/j.tetlet.2010.01.005

  日期：2010.3

  Regiospecific construction of 3-alkyl-4-hydroxybenzimidazoles is detailed. The synthetic route involves a novel O- to N-acyl transfer reaction to address the observed exclusive O-acylation of 2-amino-3-nitrophenol starting material. This efficient route provides the targeted 3-alkyl-4-hydroxybenzimidazoles in good yields, in five steps, without the use of chromatographic purification. These key intermediates were subsequently elaborated, as shown, to provide acylsulfonamide-derived potent EP3 receptor antagonists. (C) 2010 Elsevier Ltd. All rights reserved.