(R)-5-[(4,5-Diphenyl-oxazol-2-ylmethyl)-amino]-5,6,7,8-tetrahydro-naphthalen-1-ol | 187994-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R)-5-[(4,5-Diphenyl-oxazol-2-ylmethyl)-amino]-5,6,7,8-tetrahydro-naphthalen-1-ol
• CAS: 187994-49-6
• 化学式: C₂₆H₂₄N₂O₂
• 分子量: 396.489
• InChiKey: TVYVPXMWOXKXFM-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.29
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-5-[(4,5-Diphenyl-oxazol-2-ylmethyl)-amino]-5,6,7,8-tetrahydro-naphthalen-1-ol 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 sodium;2-[[(5R)-5-[(4,5-diphenyl-1,3-oxazol-2-yl)methylamino]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]acetate
  参考文献：
  名称：

  Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: Orally active prostacyclin mimetics. Part 2

  摘要：

  Synthetic and biological evaluation of novel diphenyloxazole derivatives containing a pyrrolidine ring, as a prostacyclin mimetic without the PG skeleton, are described. Asymmetric reduction of a ketone using a chiral Ru complex and reductive amination by NaBH4 produces four isomers of the tetrahydronaphthalene ring and the pyrrolidine ring with high stereoselectivity. FR193262 (4), (R,R)-diphenyloxazolyl pyrrolidine derivative, displays high potency and agonist efficacy at the IP receptor and has good bioavailability in rats and dogs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.042
• 作为产物：
  描述：

  (1R)-1-(4,5-diphenyloxazol-2-yl)methylamino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-5-[(4,5-Diphenyl-oxazol-2-ylmethyl)-amino]-5,6,7,8-tetrahydro-naphthalen-1-ol
  参考文献：
  名称：

  Discovery of new diphenyloxazole derivatives containing a pyrrolidine ring: Orally active prostacyclin mimetics. Part 2

  摘要：

  Synthetic and biological evaluation of novel diphenyloxazole derivatives containing a pyrrolidine ring, as a prostacyclin mimetic without the PG skeleton, are described. Asymmetric reduction of a ketone using a chiral Ru complex and reductive amination by NaBH4 produces four isomers of the tetrahydronaphthalene ring and the pyrrolidine ring with high stereoselectivity. FR193262 (4), (R,R)-diphenyloxazolyl pyrrolidine derivative, displays high potency and agonist efficacy at the IP receptor and has good bioavailability in rats and dogs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.042