2-ethoxy-3-phenethyl-2-(trifluoromethyl)oxirane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-ethoxy-3-phenethyl-2-(trifluoromethyl)oxirane
• 英文别名: 2-ethoxy-3-(2-phenylethyl)-2-(trifluoromethyl)oxirane
• 化学式: C₁₃H₁₅F₃O₂
• 分子量: 260.256
• InChiKey: QLRHSAZKQFSJJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethoxy-3-phenethyl-2-(trifluoromethyl)oxirane 在 吡啶 、 盐酸 、 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl acetate
  参考文献：
  名称：

  TRICYCLIC INDOLE DERIVATIVES USEFUL ENDOTHELIAL LIPASE INHIBITORS

  摘要：

  本发明涉及三环吲哚衍生物、包含它们的制药组合物，以及它们在治疗受内皮细胞脂肪酶调节的疾病和病况，例如心血管疾病中的应用。

  公开号：

  US20130210806A1

文献信息

• 1-Trifluoromethyl Epoxy Ethers. Effect of Hexafluoro-2-propanol on Reactions with Secondary Aromatic Amines: Synthesis of 3-Trifluoromethyl Indole Derivatives
  作者：Isabelle Rodrigues、Danièle Bonnet-Delpon、Jean-Pierre Bégué

  DOI：10.1021/jo005751y

  日期：2001.3.1

  Trifluoromethyl epoxy ethers 1 and 2 reacted with aromatic amines in hexafluoro-2-propanol at room temperature providing trifluoromethyl indolinols 3 and 4 in excellent isolated yields. 3-Trifluoromethyl indoles 9 and 10 could be prepared by treatment of indolinols with SOCl(2).

  三氟甲基环氧醚1和2在六氟-2-丙醇中与芳族胺在室温下反应，以优异的分离收率得到三氟甲基吲哚酚3和4。3-三氟甲基吲哚9和10可以通过用SOCl（2）处理吲哚酚来制备。
• Synthesis of allylic trifluoromethyl alcohols from 1-trifluoromethyl-epoxy ethers
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Andrei Kornilov、Nathalie Fischer-Durand

  DOI：10.1016/s0022-1139(96)03452-5

  日期：1996.9

  α-Thiophenyl ketones are easily available by the regioselective ring-opening of 1-trifluoromethyl-epoxy ethers with phenyl sodium thiolate. Their in situ reduction with NaBH4, followed by oxidation with NaIO4 and thermal decomposition of the resultant sulphoxides, provided allylic trifluoromethyl alcohols in high overall yield.

  通过1-三氟甲基-环氧醚与苯基硫醇钠的区域选择性开环，可轻松获得α-噻吩酮。它们用NaBH 4原位还原，然后用NaIO 4氧化并热分解生成的亚砜，提供了高总收率的烯丙基三氟甲基醇。
• Tricyclic indole derivatives useful endothelial lipase inhibitors
  申请人：Janssen Pharmaceutica, NV

  公开号：US09216998B2

  公开（公告）日：2015-12-22

  The present invention is directed to tricyclic indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by endothelial lipase, for example, cardiovascular disorders.

  本发明涉及三环吲哚衍生物、含有它们的药物组合物以及它们在治疗受内皮脂酶调节的疾病和病症中的应用，例如心血管疾病。
• Ring-Opening of 1-CF3-Substituted Epoxy Ethers with Carboxylic, Thiocarboxylic, and Phosphinic Acids in Basic Medium and in Hexafluoro-2-propanol
  作者：Jernej Iskra、Danièle Bonnet-Delpon、Jean-Pierre Bégué

  DOI：10.1002/1099-0690(200210)2002:20<3402::aid-ejoc3402>3.0.co;2-m

  日期：2002.10

  Ring-opening of 1-CF3-substituted epoxy ethers with carboxylic acids was achieved in Et3N as solvent, and alpha-CF3-substituted acyloins and corresponding esters were obtained in good yields. In hexafluoro-2-propanol (HFIP) as solvent, the carboxylic acids acted as nucleophiles, and alpha-carbonyloxy trifluoromethyl ketones were isolated in good yields. After reduction, CF3-substituted glycols were obtained as monoesters on one or the other hydroxy group. This reaction also allowed the preparation of alpha-carbonylsulfanyl- and alpha-phosphoryloxy trifluoromethyl ketones and corresponding alcohols. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
• US9216998B2
  申请人：——

  公开号：US9216998B2

  公开（公告）日：2015-12-22