3-methyl-1-(3,5-bistrifluoromethylphenyl)-1-butyne-3-ol | 331237-50-4

• 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: 3-methyl-1-(3,5-bistrifluoromethylphenyl)-1-butyne-3-ol
• 英文别名: 4-[3,5-Bis(trifluoromethyl)phenyl]-2-methylbut-3-yn-2-ol
• CAS: 331237-50-4
• 化学式: C₁₃H₁₀F₆O
• 分子量: 296.212
• InChiKey: OAHSTAWLWFWXDX-UHFFFAOYSA-N

物化性质

• 沸点：
  266.6±40.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-methyl-1-(3,5-bistrifluoromethylphenyl)-1-butyne-3-ol 在 sodium hydroxide 作用下， 以 环己烷 为溶剂， 反应 2.0h， 以15.24 g的产率得到3,5-双三氟甲基苯乙炔
  参考文献：
  名称：

  Fluorinated phenylethynyl-terminated imide oligomers with reduced melt viscosity and enhanced melt stability

  摘要：

  Two novel fluorinated phenyethynyl-contained endcapping agents, 4-(3-trifluoromethyl-1-phenylethynyl)phthalic anhydride (3F-PEPA) and 4-(3,5-bistrifluoromethyl-1-phenylethynyl)phthalic anhydride (6F-PEPA) were synthesized, which were employed to synthesize two fluorinated model compounds, N-phenyl-4(3-trifluoromethyl)-phenylethynylphthalimide (3F-M) and N-phenyl-4(3,5-bitrifluoromethyl)-phenylethynyl phthalimide (6F-M). The thermal cure kinetics of 3F-M and 6F-M were analyzed using DSC and compared to the unfluorinated derivative, N-phenyl-4-phenylethynylphthalimide (PEPA-M). The thermal cure temperatures of 3F-M and 6F-M were 399 and 412 degrees C, which were 22 and 35 degrees C higher than that of PEPA-M, respectively. The thermal cure kinetics of 3F-M and 6F-M best fit a first-order rate law, although 3F-M and 6F-M reacted slower than PEPA-M. However, the exothermic enthalpy of 3F-M and 6F-M were only half of PEPA-M. Based on the model compounds study, a series of fluorinated phenylethynyl-terminated imide oligomers (F-PETIs) with different calculated molecular weights (Calc'd M-n) were synthesized by thermal polycondensation of 2,3,3',4'-biphenyltetracarboxylic acid dianhydride (a-BPDA) and 3,4'-oxydianiline (3,4'-ODA) using 3F-PEPA or 6F-PEPA as the endcapping agent. The substituent effects of the trifluoromethyl (-CF3) groups on the thermal cure behavior and melt processability of F-PETIs were systematically investigated. Experimental results reveal that the melt processability of F-PETI was apparently improved by the reduced resin melt viscosities and the enhanced melt stability due to the incorporation of the -CF3 groups in the imide backbone. All of those F-PETIs exhibit outstanding thermal and mechanical properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.11.007
• 作为产物：
  描述：

  1-bromo-3,5-(bitrifluoromethyl)benzene 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 反应 8.0h， 生成 3-methyl-1-(3,5-bistrifluoromethylphenyl)-1-butyne-3-ol
  参考文献：
  名称：

  Fluorinated phenylethynyl-terminated imide oligomers with reduced melt viscosity and enhanced melt stability

  摘要：

  Two novel fluorinated phenyethynyl-contained endcapping agents, 4-(3-trifluoromethyl-1-phenylethynyl)phthalic anhydride (3F-PEPA) and 4-(3,5-bistrifluoromethyl-1-phenylethynyl)phthalic anhydride (6F-PEPA) were synthesized, which were employed to synthesize two fluorinated model compounds, N-phenyl-4(3-trifluoromethyl)-phenylethynylphthalimide (3F-M) and N-phenyl-4(3,5-bitrifluoromethyl)-phenylethynyl phthalimide (6F-M). The thermal cure kinetics of 3F-M and 6F-M were analyzed using DSC and compared to the unfluorinated derivative, N-phenyl-4-phenylethynylphthalimide (PEPA-M). The thermal cure temperatures of 3F-M and 6F-M were 399 and 412 degrees C, which were 22 and 35 degrees C higher than that of PEPA-M, respectively. The thermal cure kinetics of 3F-M and 6F-M best fit a first-order rate law, although 3F-M and 6F-M reacted slower than PEPA-M. However, the exothermic enthalpy of 3F-M and 6F-M were only half of PEPA-M. Based on the model compounds study, a series of fluorinated phenylethynyl-terminated imide oligomers (F-PETIs) with different calculated molecular weights (Calc'd M-n) were synthesized by thermal polycondensation of 2,3,3',4'-biphenyltetracarboxylic acid dianhydride (a-BPDA) and 3,4'-oxydianiline (3,4'-ODA) using 3F-PEPA or 6F-PEPA as the endcapping agent. The substituent effects of the trifluoromethyl (-CF3) groups on the thermal cure behavior and melt processability of F-PETIs were systematically investigated. Experimental results reveal that the melt processability of F-PETI was apparently improved by the reduced resin melt viscosities and the enhanced melt stability due to the incorporation of the -CF3 groups in the imide backbone. All of those F-PETIs exhibit outstanding thermal and mechanical properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.11.007

文献信息

• Insecticidal and acaricidal composition, and methods of using the same
  申请人：AGRO-KANESHO CO., LTD.

  公开号：US20020156115A1

  公开（公告）日：2002-10-24

  The present invention provides an insecticidal or acaricidal composition having an excellent pesticidal effect and a high safety, containing, as an active ingredient, a pyrazolyl compound of the following general formula (I): 1 wherein A represents a hydrogen atom; an alkyl group which may be substituted; an alkenyl group which may be substituted; an alkynyl group which may be substituted; a tri-substituted silyl group substituted with an alkyl group and/or an aryl group: an aryl group which may be substituted; or a heterocyclic group which may be substituted; B represents a single bond; a group of the formula: —(G 1 ) n —G 2 —(G 1 ) m — wherein G 1 represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group, G 2 represents an alkylene group, an alkenylene group or an alkynylene group, and n and m are independent from each other and represent 0 or 1; carbonyl group; a group of the formula: —CH 2 —O—N═C(R 3 )— wherein R 3 represents a hydrogen atom, an alkyl group or a haloalkyl group; or a group of the formula: —CH═N—O—(CR 3 R 4 ) n — wherein R 3 and R 4 each represents a hydrogen atom, an alkyl group or a haloalkyl group; and n is 0 or 1, R 1 represents a hydrogen atom; a halogen atom, an alkyl group which may be substituted; an alkenyl group which may be substituted; an alkynyl group which may be substituted; an alkoxyl group which may be substituted; or an aryl group which may be substituted, R 2 represents a hydrogen atom; an alkyl group; a haloalkyl group; or an aryl group which may be substituted, and D represents a group of the formula: —C(═Y)COX wherein X represents a hydroxyl group, an alkoxyl group or an alkylamino group, Y represents a group of the formula: CH—(G 3 ) n —G 4 — wherein G 3 represents an oxygen atom or a sulfur atom, G 4 represents an alkyl group or a haloalkyl group, and n represents 0 or 1, a group of the formula: N—O—G 4 wherein G 4 represents an alkyl group or a haloalkyl group; or a group of the formula: —N(R 5 )CO 2 G 5 wherein R 5 represents an alkyl group, an alkenyl group, an alkynyl group, an alkylthioalkyl group or an alkoxyalkyl group, and G 5 represents an alkyl group.

  本发明提供了一种具有优异杀虫或杀螨效果且具有高安全性的杀虫剂或杀螨剂组合物，其包含以下通式（I）的吡唑基化合物作为活性成分：其中A代表氢原子；可以被取代的烷基基团；可以被取代的烯基基团；可以被取代的炔基基团；取代的三取代硅基团，取代的烷基基团和/或芳基团；可以被取代的芳基团；或可以被取代的杂环基团；B代表单键；具有以下结构的基团：—（G1）n—G2—（G1）m—其中G1代表氧原子、硫原子、亚硫酰基或磺酰基，G2代表烷基基团、烯基基团或炔基基团，n和m是独立的，表示0或1；羰基基团；具有以下结构的基团：—CH2—O—N═C(R3)—其中R3代表氢原子、烷基基团或卤代烷基基团；或具有以下结构的基团：—CH═N—O—（CR3R4）n—其中R3和R4各自代表氢原子、烷基基团或卤代烷基基团；n为0或1，R1代表氢原子；卤素原子、可以被取代的烷基基团；可以被取代的烯基基团；可以被取代的炔基基团；可以被取代的烷氧基基团；或可以被取代的芳基团；R2代表氢原子；烷基基团；卤代烷基基团；或可以被取代的芳基团，D代表以下结构的基团：—C(═Y)COX，其中X代表羟基、烷氧基或烷基氨基，Y代表结构：CH—（G3）n—G4—其中G3代表氧原子或硫原子，G4代表烷基基团或卤代烷基基团，n代表0或1，具有以下结构的基团：N—O—G4其中G4代表烷基基团或卤代烷基基团；或具有以下结构的基团：—N(R5)CO2G5其中R5代表烷基基团、烯基基团、炔基基团、烷基硫基基团或烷氧基烷基基团，G5代表烷基基团。
• Visible light mediated, metal-free carbene transfer reactions of diazoalkanes with propargylic alcohols
  作者：Feifei He、Rene M. Koenigs

  DOI：10.1039/c9cc00927b

  日期：——

  The development of efficient carbene transfer reactions under mild reaction conditions is very important to access small molecules for applications in organic synthesis and drug discovery. Herein, we describe the application of blue light in photochemical carbene transfer reactions of donor acceptor diazoalkanes under mild reaction conditions with propargylic alcohols, which provides – in contrast

  在温和的反应条件下开发有效的卡宾转移反应对于获得用于有机合成和药物发现的小分子非常重要。在此，我们描述了蓝光在温和的条件下与供体醇与供体受体重氮烷的光化学卡宾转移反应中的应用，与常规的金属催化的卡宾转移反应相比，它提供了进入环丙烯的途径。
• Insecticidal and acaricidal agent
  申请人：AGRO-KANESHO CO., LTD.

  公开号：US20030191171A1

  公开（公告）日：2003-10-09

  The present invention provides an insecticidal or acaricidal composition having an excellent pesticidal effect and a high safety, containing, as an active ingredient, a pyrazolyl compound of the following general formula (I): 1 wherein A represents a hydrogen atom; an alkyl group which may be substituted; an alkenyl group which may be substituted; an alkynyl group which may be substituted; a tri-substituted silyl group substituted with an alkyl group and/or an aryl group: an aryl group which may be substituted; or a heterocyclic group which may be substituted; B represents a single bond; a group of the formula: -(G 1 ) n -G 2 -(G 1 ) m - wherein G 1 represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group, G 2 represents an alkylene group, an alkenylene group or an alkynylene group, and n and m are independent from each other and represent 0 or 1; carbonyl group; a group of the formula: —CH 2 —O—N═C(R 3 )— wherein R 3 represents a hydrogen atom, an alkyl group or a haloalkyl group; or a group of the formula: —CH═N—O—(CR 3 R 4 ) n — wherein R 3 and R 4 each represents a hydrogen atom, an alkyl group or a haloalkyl group; and n is 0 or 1, R 1 represents a hydrogen atom; a halogen atom, an alkyl group which may be substituted; an alkenyl group which may be substituted; an alkynyl group which may be substituted; an alkoxyl group which may be substituted; or an aryl group which may be substituted, R 2 represents a hydrogen atom; an alkyl group; a haloalkyl group; or an aryl group which may be substituted, and D represents a group of the formula: —C(═Y)COX wherein X represents a hydroxyl group, an alkoxyl group or an alkylamino group, Y represents a group of the formula: CH-(G 3 ) n -G 4 - wherein G 3 represents an oxygen atom or a sulfur atom, G4 represents an alkyl group or a haloalkyl group, and n represents 0 or 1, a group of the formula: N—O-G 4 wherein G 4 represents an alkyl group or a haloalkyl group; or a group of the formula: —N(R 5 )CO 2 G 5 wherein R 5 represents an alkyl group, an alkenyl group, an alkynyl group, an alkylthioalkyl group or an alkoxyalkyl group, and G 5 represents an alkyl group.

  本发明提供了一种具有优异的杀虫或杀螨效果和高安全性的杀虫剂或杀螨剂组合物，其包含以下通式（I）的吡唑基化合物作为活性成分：其中，A表示氢原子；可以被取代的烷基基团；可以被取代的烯基基团；可以被取代的炔基基团；被取代的三取代硅基团，其被取代的基团为烷基和/或芳基；可以被取代的芳基基团；或可以被取代的杂环基团；B表示单键；一个式子的基团：-(G1)n-G2-(G1)m-，其中，G1表示氧原子、硫原子、亚砜基或磺酰基，G2表示烷基、烯基或炔基，n和m是独立的，表示0或1；羰基基团；一个式子的基团：—CH2—O—N═C(R3)—，其中，R3表示氢原子、烷基或卤代烷基；或一个式子的基团：—CH═N—O—(CR3R4)n—，其中，R3和R4分别表示氢原子、烷基或卤代烷基；n为0或1；R1表示氢原子；卤原子、可以被取代的烷基基团；可以被取代的烯基基团；可以被取代的炔基基团；可以被取代的烷氧基；或可以被取代的芳基基团；R2表示氢原子；烷基；卤代烷基；或可以被取代的芳基基团；D表示一个式子的基团：—C(═Y)COX，其中，X表示羟基、烷氧基或烷基氨基基团，Y表示一个式子的基团：CH-(G3)n-G4-，其中，G3表示氧原子或硫原子，G4表示烷基或卤代烷基，n表示0或1；一个式子的基团：N—O-G4，其中，G4表示烷基或卤代烷基；或一个式子的基团：—N(R5)CO2G5，其中，R5表示烷基、烯基、炔基、烷硫基烷基或烷氧基烷基，G5表示烷基。
• INSECTICIDAL AND ACARICIDAL AGENTS
  申请人：Agro-Kanesho Co., Ltd.

  公开号：EP1219173A1

  公开（公告）日：2002-07-03

  The present invention provides an insecticidal or acaricidal agent having an excellent pesticidal effect and a high safety. Namely, the present invention resides in an insecticidal or acaricidal agent comprising, as an active ingredient, a pyrazolyl derivative of the following general formula (I): wherein A represents a hydrogen atom; an alkyl group which may be substituted; an alkenyl group which may be substituted; an alkynyl group which may be substituted; a tri-substituted silyl group substituted with an alkyl group and/or an aryl group: an aryl group which may be substituted; or a heterocyclic group which may be substituted; B represents a single bond; a group of the formula: -(G1)n-G2-(G1)m- wherein G1 represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group, G2 represents an alkylene group, an alkenylene group or an alkynylene group, and n and m are independent from each other and represent 0 or 1; carbonyl group; a group of the formula: -CH2-O-N=C(R3)-wherein R3 represents a hydrogen atom, an alkyl group or a haloalkyl group; or a group of the formula: -CH=N-O-(CR3R4)n- wherein R3 and R4 each represents a hydrogen atom, an alkyl group or a haloalkyl group; and n is 0 or 1, R1 represents a hydrogen atom; a halogen atom, an alkyl group which may be substituted; an alkenyl group which may be substituted; an alkynyl group which may be substituted; an alkoxyl group which may be substituted; or an aryl group which may be substituted, R2 represents a hydrogen atom; an alkyl group; a haloalkyl group; or an aryl group which may be substituted, and D represents a group of the formula: -C(=Y)COX wherein X represents a hydroxyl group, an alkoxyl group or an alkylamino group, Y represents a group of the formula: CH-(G3)n-G4 wherein G3 represents an oxygen atom or a sulfur atom, G4 represents an alkyl group or a haloalkyl group, and n represents 0 or 1, a group of the formula: N-O-G4 wherein G4 represents an alkyl group or a haloalkyl group; or a group of the formula: -N(R5)CO2G5 wherein R5 represents an alkyl group, an alkenyl group, an alkynyl group, an alkylthioalkyl group or an alkoxyalkyl group, and G5 represents an alkyl group.

  本发明提供了一种杀虫或杀螨剂，具有极佳的杀虫效果和极高的安全性。即，本发明涉及一种杀虫或杀螨剂，其活性成分包括以下通式（I）的吡唑衍生物： 式中 A 代表氢原子；可被取代的烷基；可被取代的烯基；可被取代的炔基；被烷基和/或 芳基取代的三取代硅烷基；可被取代的芳基；或可被取代的杂环基； B 代表单键；式中的基团：-(G1)n-G2-(G1)m-，其中 G1 代表氧原子、硫原子、亚砜基或磺酰基，G2 代表亚烯基、亚烯基或亚炔基，n 和 m 互不相关，代表 0 或 1；羰基；式中的基团：-CH2-O-N=C(R3)-其中 R3 代表氢原子、烷基或卤代烷基；或式中的基团：-CH=N-O-(CR3R4)n-，其中 R3 和 R4 分别代表氢原子、烷基或卤代烷基；且 n 为 0 或 1，R1 代表氢原子、卤素原子、可被取代的烷基、可被取代的烯基、可被取代的炔基或卤代烷基；R2 代表氢原子、烷基、卤代烷基或可被取代的芳基，D 代表式中的一个基团：-其中 X 代表羟基、烷氧基或烷基氨基，Y 代表式中的一个基团：CH-(G3)n-G4，其中 G3 代表氧原子或硫原子，G4 代表烷基或卤代烷基，且 n 代表 0 或 1，代表式中的一个基团：N-O-G4，其中 G4 代表烷基或卤代烷基；或式中的基团：-N(R5)CO2G5，其中 R5 代表烷基、烯基、炔基、烷硫基或烷氧烷基，G5 代表烷基。
• Transition Metal-Free <i>trans</i>-Selective Alkynylboration of Alkynes
  作者：Marina Nogami、Keiichi Hirano、Misae Kanai、Chao Wang、Tatsuo Saito、Kazunori Miyamoto、Atsuya Muranaka、Masanobu Uchiyama

  DOI：10.1021/jacs.7b06212

  日期：2017.9.13

  We report the first transition metal-free and trans-selective alkynylboration reaction of alkynes. This unprecedented carboboration reaction is enabled by pseudo-intramolecular activation of alkynylboronates using propargylic alcohols. The carboboration affords 4-alkynyl-1,2-oxaborol-2(5H)-ols, which are not only versatile building blocks but also exhibit strong violet blue fluorescence emission.