(±)-6-methoxy-1-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-ol | 188726-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (±)-6-methoxy-1-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-ol
• 英文别名: 1-Hydroxy-6-methoxy-1-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalene；6-methoxy-1-(trifluoromethyl)-3,4-dihydro-2H-naphthalen-1-ol
• CAS: 188726-45-6
• 化学式: C₁₂H₁₃F₃O₂
• mdl: MFCD16432476
• 分子量: 246.229
• InChiKey: KQQKDNLMXYUGGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (±)-6-methoxy-1-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-ol 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Discovery and stereoselective synthesis of the novel isochroman neurokinin-1 receptor antagonist ‘CJ-17,493’

  摘要：

  A novel central nervous system (CNS) selective neurokinin-1 (NK1) receptor antagonist, (2S, 3S)-3-[(1R)-6-methoxy- 1-methyl-1-trifluoromethylisochroman-7-yl]-methylamino-2-phenylpiperidine 'CJ-17,493'( compound (+)-1), was synthesized stereoselectively using a kinetic resolution by lipase-PS as a key step. Compound (+)-1 displayed high and selective affinity (K-i = 0.2 nM) for the human NK1 receptor in IM-9 cells, potent activity in the [Sar(9), Met(O-2)(11)] SP-induced gerbil tapping model (ED50 = 0.04 mg/kg, sc) and in the ferret cisplatin (10 mg/kg, ip)-induced anti-emetic activity model (vomiting: ED90 = 0.07 mg/kg, sc), all levels of activity comparable with those of CP-122,721. In addition, compound (+)-1 exhibited linear pharmacokinetics rather than the super dose-proportionality of CP-122,721 and this result provides a potential solution for the clinical issue observed with CP-122,721. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.047
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以57 %的产率得到(±)-6-methoxy-1-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  用南极假丝酵母脂肪酶 A 动力学拆分环状叔醇

  摘要：

  使用己酸乙烯酯作为 Na 2 CO 3 的酰基供体是使用市售的外消旋叔醇 KR 大幅提高反应速率、底物范围和产物稳定性的关键来自南极洲念珠菌的脂肪酶 A。 KR 条件适用于含有四氢化萘、二氢茚、苯并二氢吡喃和硫代苯并二氢吡喃部分的环状叔醇，产生具有优异对映选择性的酯。

  DOI：

  10.1002/ejoc.202400242

文献信息

• Substituted benzylaminopiperidine compounds
  申请人：Pfizer Inc.

  公开号：US06329396B1

  公开（公告）日：2001-12-11

  The invention provides a substituted benzylaminopiperidine compounds that are useful in the treatment of gastrointestinal disorders; central nervous system (CNS) disorders; inflammatory disease; emesis; urinary incontinence; pain; migraine; sunburn; diseases, disorders and adverse conditions caused by Heliobacter pylori; or angiogenesis, especially CNS disorders in a mammalian subject, especially in humans.

  这项发明提供了一种取代苄基氨基哌啶化合物，可用于治疗胃肠道疾病；中枢神经系统（CNS）疾病；炎症性疾病；呕吐；尿失禁；疼痛；偏头痛；晒伤；由幽门螺杆菌引起的疾病、疾病和不良症状；或血管生成，尤其是在哺乳动物主体中的中枢神经系统疾病，尤其是在人类中。
• Synthesis of aromatic compounds containing a 1,1-dialkyl-2-trifluoromethyl group, a bioisostere of the tert-alkyl moiety
  作者：Hirotaka Tanaka、Yuji Shishido

  DOI：10.1016/j.bmcl.2007.09.053

  日期：2007.11

  1,1-Dialkyl-2-perfluoroalkyl compounds, which are potential metabolically stable bioisosteres of the tert-alkyl moiety, have been synthesized from the corresponding tertiary alcohols using titanium (IV) chloride-dimethylzinc or trimethylaluminium as the source of the methyl group. The synthetic methods proved to be versatile for synthesizing 1,1-dimethyl-2,2,2-trifluoroethyl compounds and analogs, including compounds containing aromatic and heterocyclic rings. (C) 2007 Elsevier Ltd. All rights reserved.