2-[[3-(三氟甲基)苯氧基]甲基]环氧乙烷 | 585-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[[3-(三氟甲基)苯氧基]甲基]环氧乙烷
• 英文名称: 2-((3-(trifluoromethyl)phenoxy)methyl)ethylene oxide
• 英文别名: 2-((3-(trifluoromethyl)phenoxy)methyl)oxirane；(3-trifluoromethyl-phenoxymethyl)-oxirane；3-(2,3-epoxy-propoxy)-α,α,α-trifluoro-toluene；3-(2,3-Epoxy-propoxy)-α,α,α-trifluor-toluol；1,2-epoxy-3-(3-trifluoromethyl)phenoxypropane；1,2-epoxy-3-(3-trifluoromethylphenoxy)propane；2-[3-(Trifluoromethyl)phenoxymethyl]oxirane；2-[[3-(trifluoromethyl)phenoxy]methyl]oxirane
• CAS: 585-45-5
• 化学式: C₁₀H₉F₃O₂
• mdl: MFCD11131173
• 分子量: 218.175
• InChiKey: NBXFAQFMTDGEQN-UHFFFAOYSA-N

物化性质

• 沸点：
  246.9±40.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-[[3-(三氟甲基)苯氧基]甲基]环氧乙烷 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 甲醇 、 异丙醇 、 丙酮 为溶剂， 60.0 ℃ 、2.0 MPa 条件下， 反应 144.0h， 生成 (4-{2-[2-Hydroxy-3-(3-trifluoromethyl-phenoxy)-propylamino]-ethoxy}-phenoxy)-acetic acid methyl ester
  参考文献：
  名称：

  Selective .beta.3-adrenergic agonists of brown adipose tissue and thermogenesis. 2. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetamides

  摘要：

  The ester methyl [4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetate (1) (R1 = OMe) had previously been identified as the most interesting member of a series of selective beta-3-adrenergic agonists of brown adipose tissue and thermogenesis in the rat. In vivo it acts mainly via the related acid 1 (R1 = OH). Amides have been examined to determine whether they have advantages over the ester. In particular, in the rat and dog the half-lives of amides of appropriate potency were no longer than those of the ester. The amide (S)-4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]-N-(2-methoxyethyl)phenoxyacetamide [S-27, ICI D7114] was selected as having properties consistent with a sustained-release formulation should that prove necessary. Unlike the ester it is resistant to hydrolysis in the gut lumen. Further testing of ICI D7114 has shown that in the rat, cat, and dog it stimulates the beta-3-adrenergic receptor in brown adipose tissue at doses lower than those at which it affects beta-1- and beta-2-adrenergic receptors in other tissues. Slimming effects were observed in the dog. ICI D7114 may be a selective thermogenic agent in man and may be useful in the treatment of obesity and diabetes.

  DOI：

  10.1021/jm00088a010
• 作为产物：
  描述：

  间三氟甲基苯酚 、 环氧氯丙烷 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 16.67h， 以95%的产率得到2-[[3-(三氟甲基)苯氧基]甲基]环氧乙烷
  参考文献：
  名称：

  一种β-羰基磷酸酯的制备方法

  摘要：

  本发明提供了一种β‑羰基磷酸酯的制备方法，以环氧化合物与亚磷酸三烷基酯进行区域选择性的开环反应生成β‑羟基磷酸酯中间体，随后氧化得到β‑羰基磷酸酯，该方法反应条件温和，操作简便，无需无水溶剂及氧气的保护，更加适合规模化生产。该制备方法所合成的β‑羰基磷酸酯，可以作为多种前列腺素药物合成的重要中间体，例如曲沃前列腺素、比马前列腺素及他氟前列腺素等。

  公开号：

  CN107011377B

文献信息

• [EN] ANALGESIC THAT BINDS FILAMIN A<br/>[FR] ANALGÉSIQUE QUI SE LIE À LA FILAMINE A
  申请人：PAIN THERAPEUTICS INC

  公开号：WO2010051374A1

  公开（公告）日：2010-05-06

  A compound, composition and method are disclosed that can provide analgesia. A contemplated compound has a structure that corresponds to Formula A, wherein A, B, X, R1, R2, R7 and R8, and the dashed lines are defined within.

  公开了一种化合物、组合物及方法，能够提供镇痛效果。所考虑的化合物具有与式A相对应的结构，其中A、B、X、R1、R2、R7和R8以及虚线均在定义范围内。
• Studies on Agents with Vasodilator and .BETA.-Blocking Activities. II.
  作者：Toshimi SEKI、Takayuki TAKEZAKI、Rikio OHUCHI、Hiroshi OHUYABU、Yoshitaka TANIMOTO、Takashi YAMAGUCHI、Norinobu SAITOH、Tsutomu ISHIMORI、Kikuo YASUDA

  DOI：10.1248/cpb.43.247

  日期：——

  A series of phenoxypropanolamines having a hydrazinopyridazinyl moiety was synthesized. Their hypotensive and β-blocking activities were evaluated after intravenous administration of the compounds to anethetized rats.Some of them exhibited both activities. In particular, compound 20k is a candidate for clinical use due to its hypotensive activity, equal to that of hydralazine, and its β-blocking activity, 2.7-fold more potent than that of propranolol.

  一系列含有哒嗪基肼结构的苯氧丙醇胺类化合物被合成，并通过静脉注射给麻醉大鼠后评估了它们的降压和β阻断活性。其中一些化合物显示了这两种活性。特别是化合物20k，由于其降压活性与肼达嗪相当，且β阻断活性比普萘洛尔强2.7倍，因此被认为是临床应用的候选药物。
• Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds
  作者：Xiao-Yu Lu、Chu-Ting Yang、Jing-Hui Liu、Zheng-Qi Zhang、Xi Lu、Xin Lou、Bin Xiao、Yao Fu

  DOI：10.1039/c4cc09321f

  日期：——

  A copper-catalyzed cross-coupling reaction of epoxides with arylboronates is described. This reaction is not limited to aromatic epoxides, because aliphatic epoxides are also suitable substrates. In addition, N-sulfonyl aziridines can be successfully converted into the products. This reaction provides convenient access to beta-phenethyl alcohols, which are valuable synthetic intermediates.

  描述了铜与芳基硼酸酯的铜催化的交叉偶联反应。该反应不限于芳族环氧化物，因为脂族环氧化物也是合适的底物。另外，N-磺酰基氮丙啶可以成功地转化为产物。该反应可方便地获得作为有价值的合成中间体的β-苯乙醇。
• Copper-catalyzed/mediated borylation reactions of epoxides with diboron reagents: access to β-hydroxyl boronic esters
  作者：Ebrahim-Alkhalil M. A. Ahmed、Xi Lu、Tian-Jun Gong、Zhen-Qi Zhang、Bin Xiao、Yao Fu

  DOI：10.1039/c6cc07924e

  日期：——

  We report the first copper-catalyzed/mediated borylative ring opening reaction of epoxides.

  我们报道了环氧的第一个铜催化/介导的硼化开环反应。
• SYNTHESIS OF THE RIGID ANALOGUES OF AN SSRI BENZENEPROPANAMINE
  作者：S.T.V.S. Kiran Kumar、V.L. Sharma、Shipra Srivastava、Kalpana Bhandari、Girija Shander、H.K. Singh

  DOI：10.1007/s00044-004-0051-5

  日期：2004.7

  and ethyl acrylate and evaluated for antidepressant activity. The compounds were fully characterized by spectral and elemental analyses, and were tested for their effect on gross behavior, antireserpine and anorexigenic activity. No effect was observed on gross behavior and some of them showed fluoxetine like antireserpine and anorexigenic activity.

  从甲胺开始，按照六步反应顺序，制备了几种1-（取代的苯氧基）-3-[4-（4-三氟甲基）苯氧基]哌啶-1-基}丙-2-醇（str.II）。丙烯酸乙酯并评估其抗抑郁活性。通过光谱和元素分析对化合物进行了全面表征，并测试了它们对总体行为，抗利血平和厌食活性的影响。没有观察到对总体行为的影响，其中一些表现出氟西汀像抗利血平和厌食活性。