3-羟基-3-(三氟甲基)环己烯 | 118143-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-羟基-3-(三氟甲基)环己烯
• 英文名称: 1-(trifluoromethyl)-2-cyclohexen-1-ol
• 英文别名: 1-(Trifluoromethyl)cyclohex-2-en-1-ol
• CAS: 118143-28-5
• 化学式: C₇H₉F₃O
• 分子量: 166.143
• InChiKey: DFFKUOBCTWPVOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  3-羟基-3-(三氟甲基)环己烯 在 硫酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以28%的产率得到3-trifluoromethyl-2-cyclohexene-1-one
  参考文献：
  名称：

  三氟甲基化叔烯丙基醇与氯铬酸吡啶鎓的氧化重排制备3-三氟甲基-2-环烯酮

  摘要：

  由几种共轭烯酮的三氟甲基化制得的三氟甲基化叔烯丙醇，在少量浓H 2 SO 4的存在下，与氯铬酸吡啶鎓发生氧化重排反应，生成3-三氟甲基-2-环烯酮。

  DOI：

  10.1016/s0022-1139(99)00159-1
• 作为产物：
  描述：

  Trimethyl-[1-(trifluoromethyl)cyclohex-2-en-1-yl]oxysilane 在 四丁基氟化铵 、 水 作用下， 生成 3-羟基-3-(三氟甲基)环己烯
  参考文献：
  名称：

  三氟甲基化叔烯丙基醇与氯铬酸吡啶鎓的氧化重排制备3-三氟甲基-2-环烯酮

  摘要：

  由几种共轭烯酮的三氟甲基化制得的三氟甲基化叔烯丙醇，在少量浓H 2 SO 4的存在下，与氯铬酸吡啶鎓发生氧化重排反应，生成3-三氟甲基-2-环烯酮。

  DOI：

  10.1016/s0022-1139(99)00159-1

文献信息

• The first Cu(i)-mediated nucleophilic trifluoromethylation reactions using (trifluoromethyl)trimethylsilane in ionic liquids
  作者：Jinwi Kim、Jean'ne M. Shreeve

  DOI：10.1039/b412480b

  日期：——

  The new ionic liquids (5a-8a) were used as reaction media for nucleophilic trifluoromethylation reactions of trifluoromethyl(trimethyl)silane with (1) aryl, allyl, benzyl, and alkyl halides in Cu(I)-mediated C-C bond formation reactions, and (2) carbonyl functionalities catalyzed with Ph3P or CsF. In addition, conversion of benzyl bromide as a model compound to benzyl fluoride was examined in using

  新的离子液体（5a-8a）用作三氟甲基（三甲基）硅烷与（1）芳基，烯丙基，苄基和烷基卤化物在Cu（I）介导的CC键形成反应中的亲核三氟甲基化反应的反应介质，以及（2）用Ph3P或CsF催化的羰基官能团。另外，使用6a CsF作为氟化试剂，检查了作为模型化合物的苄基溴向苄基氟的转化。基于吗啉鎓的离子液体（6a）是一种有效的溶剂体系，可与有机溶剂媲美，并且优于在这项工作中制备的其他新离子液体以及[bmim] + [PF6]-。N-甲基恶唑烷（1），N-甲基吗啉（2），N-甲基咪唑（3）或N-甲基三唑（4）与2-（2-乙氧基乙氧基）乙基溴（BrCH2CH2OCH2CH2OCH2CH3，）或2-溴乙基甲基醚（BrCH2CH2OCH3，10）在75或105摄氏度下得到N-（2-乙氧基乙氧基）乙基或N-甲氧基乙基取代的恶唑烷鎓，吗啉鎓，咪唑鎓和三唑鎓季铵盐（1a-4a，1b -4b）与LiN（SO2C
• CsF-Catalyzed Nucleophilic Trifluoromethylation of <i>trans</i>-Enones with Trimethyl(trifluoromethyl)silane:  A Facile Synthesis of <i>trans</i>-α-Trifluoromethyl Allylic Alcohols
  作者：Rajendra P. Singh、Robert L. Kirchmeier、Jean'ne M. Shreeve

  DOI：10.1021/ol990844r

  日期：1999.10.1

  [GRAPHICS]Reactions of trans-enones, R-C=C-COR' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Pt, CFB) (la-e), with TMS-CF3 in the presence of catalytic amounts of cesium fluoride (CsF) in ethylene glycol dimethyl ether led to the formation of the corresponding trans-alpha-trifluoromethyl silyl ethers, R-C=C-C(OSiMe3)(CF3)R' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Pt, CFB) (2a-e), in essentially quantitative yield. On hydrolysis with aqueous HCl, the corresponding trans-alpha-trifluaromethyl allylic alcohols, R-C=C-C(OH)(CF3)R' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Et, CF3) (3a-e), were formed in >90% isolated yield. Under similar reaction conditions, 2-cyclohexen-1-one (1f) also gave trifluoromethyl allylic alcohols (3f) in 92% yield. The intermediates (2a-f) and products (3a-f) are liquids and were characterized by IR, H-1, (19)f and C-13 NMR, MS, and high-resolution mass spectroscopy (HRMS).
• Preparation of trifluoromethyl and other perfluoroalkyl compounds with (perfluoroalkyl)trimethylsilanes
  作者：Ramesh Krishnamurti、Donald R. Bellew、G. K. Surya Prakash

  DOI：10.1021/jo00003a017

  日期：1991.2

  The preparation of a variety of novel perfluoroalkyl-substituted compounds in high yields using easily prepared (perfluoroalkyl)trimethylsilanes (1a-c) is described. (Trifluoromethyl)-, (pentafluoroethyl)-, and (heptafluoropropyl)trimethylsilane, 1a-c, respectively, react readily with carbonyl compounds, such as aldehydes and ketones, by a fluoride-initiated catalytic process. Fluoride-initiated addition of 1 to a carbonyl group generates an oxyanionic species which then further catalyzes the reaction. Even enolizable carbonyl compounds react cleanly under the reaction conditions. A study of the scope of the reactivity of 1a toward other carbonyl groups in esters, lactones and an acid chloride was also carried out. Thus 1a reacts cleanly with five- and six-membered ring lactones. However, unactivated esters do not react under the reaction conditions. The acid chloride reacts with 1a to give a mixture of products.
• Synthetic methods and reactions. 141. Fluoride-induced trifluoromethylation of carbonyl compounds with trifluoromethyltrimethylsilane (TMS-CF3). A trifluoromethide equivalent
  作者：G. K. Surya Prakash、Ramesh Krishnamurti、George A. Olah

  DOI：10.1021/ja00183a073

  日期：1989.1
• Regioselective 1,4-trifluoromethylation of α,β-enones using ‘protect-in-situ’ methodology
  作者：Dmitri V Sevenard、Vyacheslav Ya Sosnovskikh、Alexander A Kolomeitsev、Martin H Königsmann、Gerd-Volker Röschenthaler

  DOI：10.1016/j.tetlet.2003.08.050

  日期：2003.10

  In a convenient and efficient procedure, the nucleophilic 1,4-trifluoromethylation of several alpha,beta-enones using (trifluoromethyl)trimethylsilane was achieved. The high regioselectivity of the reaction has been reached by blocking the carbonyl moiety of the electrophile with a bulky aluminum-centered Lewis acid. (C) 2003 Elsevier Ltd. All rights reserved.