1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol | 1228682-63-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol
• 英文别名: 1-Phenyl-3-[4-(trifluoromethyl)phenyl]-2-propyne-1-ol；1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-ol
• CAS: 1228682-63-0
• 化学式: C₁₆H₁₁F₃O
• 分子量: 276.258
• InChiKey: XJMNUVAEIAOKLM-UHFFFAOYSA-N

物化性质

• 沸点：
  365.5±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (E)-4-(trifluoromethyl)benzaldehyde O-[1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-yl]oxime
  参考文献：
  名称：

  Copper-Catalyzed Skeletal Rearrangement of O-Propargylic Aryloximes into Four-Membered Cyclic Nitrones - Chirality Transfer and Mechanistic Insight

  摘要：

  Copper-catalyzed skeletal rearrangement of O-propargylic aryloximes (E)-1 were carried out to afford the corresponding four-membered cyclic nitrones 2 in good to excellent yields. The optimal reactions conditions of the highly regioselective reactions involved the use of [CuCl(cod)](2) in acetonitrile at 70 degrees C. In the case of (Z)-1, however, the reaction proceeded in the absence of the copper catalysts to afford the identical compound 2 in good yields. Furthermore, the reactions were also carried out using chiral substrates (R)-1 in the presence of Cu catalysts to afford (R)-2 with good levels of chirality transfer.

  DOI：

  10.1055/s-0031-1290819
• 作为产物：
  描述：

  苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  NaH mediated isomerisation–allylation reaction of 1,3-substituted propenols

  摘要：

  建立了一种通过基础介导的异构化-烯丙基化协议来合成1,3-二取代丙烯醇的方法。报告中同时使用了二芳基和芳基-硅基底物以及取代的烯丙基溴。还进行了机理实验以阐明反应途径。

  DOI：

  10.1039/c3ob41857j

文献信息

• One-Pot Assembly of 3-Hydroxycarbazoles via Uninterrupted Propargylation/Hydroxylative Benzannulation Reactions
  作者：Chada Raji Reddy、Muppidi Subbarao、Puppala Sathish、Dattahari H. Kolgave、Ramachandra Reddy Donthiri

  DOI：10.1021/acs.orglett.9b04472

  日期：2020.1.17

  A novel strategy for the synthesis of 3-hydroxycarbazoles involving the consecutive propargylation/palladium-catalyzed hydroxylative benzannulation of indole-2-carbonyls with propargylic alcohols has been exploited. This one-pot procedure leads to a wide range of substituted 3-hydroxycarbazoles in high yield with a broad substrate scope. The method was further extended to access furano-carbazole derivatives

  已经开发了一种新的合成3-羟基咔唑的策略，该策略涉及用炔丙醇进行吲哚-2-羰基的连续炔丙基化/钯催化的羟基化苯甲环化反应。这种一锅法可高产率地产生广泛范围的取代3-羟基咔唑，并具有广泛的底物范围。该方法进一步扩展为通过串联环环法从二烷基醇中获得呋喃并咔唑衍生物。
• METHOD FOR PREPARING PROPARGYLIC ALCOHOL CATALYZED BY 2-MORPHOLINOISOBORNANE-10-THIOL
  申请人：UANG Biing-Jiun

  公开号：US20110295042A1

  公开（公告）日：2011-12-01

  A method for preparing a propargylic alcohol catalyzed by 2-morpholinoisobornane-10-thiol (MITH) is disclosed, which includes reacting R 1 CHO with R 2 CCH in the presence of R 3 ZnR 4 and MITH, wherein each of R 1 , R 2 , R 3 , and R 4 , independently, is optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkylsilyl, heterocycloalkyl, heterocycloalkenyl, aryl, aryloxy, or heteroaryl. The method can give enantioenriched propargylic alcohols with good enantioselective at low loading of MITH.

  揭示了一种由2-吗啉基异冰片烷-10-硫醇（MITH）催化制备丙炔醇的方法，该方法包括在R3ZnR4和MITH的存在下，将R1CHO与R2CCH反应，其中R1、R2、R3和R4中的每一个，独立地，可以是可选取代的烷基、烯基、环烷基、环烯基、烷基硅基、杂环烷基、杂环烯基、芳基、芳氧基或杂芳基。该方法可以在MITH的低负载下提供具有良好对映选择性的对映富集的丙炔醇。
• Ynones Merge Activation/Conjugate Addition of Chalcogenoborates ArE-Bpin (E=Se, S)
  作者：Marc G. Civit、Xavier Sanz、Christopher M. Vogels、Carles Bo、Stephen A. Westcott、Elena Fernández

  DOI：10.1002/adsc.201500650

  日期：2015.10.12

  The “pull–push” effect of the Bpin moiety in ArE-Bpin reagents (E=Se, S) is demonstrated by the Lewis acid interaction with the carbonyl group of ynones and the concomitant delivery of ArSe or ArS to the electron-deficient alkyne with impressive stereoselectivity. The two component reactivity is carried out in methanol to generate (Z)-β-(arylseleno)-α,β-unsaturated ketones and (Z)-β-(arylsulfuro)-α

  ArE-Bpin试剂（E = Se，S）中Bpin部分的“推-推”效应通过路易斯酸与炔酮的羰基相互作用以及伴随的ass或ArS传递至电子不足的炔烃来证明具有令人印象深刻的立体声选择性。在甲醇中进行两组分反应，生成（Z）-β- （芳基硒代）-α，β-不饱和酮和（Z）-β-（芳基硫代磺基）-α，β-不饱和酮对机理的理论理解。
• Copper-Catalyzed Direct Coupling of Unprotected Propargylic Alcohols with P(O)H Compounds: Access to Allenylphosphoryl Compounds under Ligand- and Base-Free Conditions
  作者：Gaobo Hu、Changkai Shan、Weizhu Chen、Pengxiang Xu、Yuxing Gao、Yufen Zhao

  DOI：10.1021/acs.orglett.6b03028

  日期：2016.12.2

  The first facile and efficient copper-catalyzed direct C–P cross-coupling of unprotected propargylic alcohols with P(O)H compounds has been developed, providing a general, one-step approach to construct valuable allenylphosphoryl frameworks with operational simplicity and high step- and atom-economy under ligand-, base-, and additive-free conditions.

  已经开发出了第一个简便而有效的铜催化的未保护的炔丙醇与P（O）H化合物的直接C–P交叉偶联方法，它提供了一种通用的一步法来构建有价值的烯丙基磷酰基骨架，且操作简便且操作步骤高。和无配体，无碱和无添加剂条件下的原子经济。
• Zn(OTf)₂-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides
  作者：Changkai Shan、Fushan Chen、Jiaoting Pan、Yuxing Gao、Pengxiang Xu、Yufen Zhao

  DOI：10.1021/acs.joc.7b02164

  日期：2017.11.3

  first facile and efficient Zn(OTf)2-catalyzed direct coupling of unprotected propargylic alcohols with arylphosphine oxides has been developed, affording a general, one-step approach to access structurally diverse γ-ketophosphine oxides via sequential Meyer–Schuster rearrangement/phospha-Michael reaction along with new C(sp3)—P and C═O bond formations, operational simplicity, and complete atom economy

  已开发出第一个简便且有效的Zn（OTf）2催化的未保护的炔丙醇与芳基膦氧化物的直接偶联反应，提供了一种通用的一步式方法，可通过顺序的Meyer-Schuster重排/膦酸酯访问结构多样的γ-酮膦氧化物。迈克尔反应以及新的C（sp 3）-P和C═O键的形成，操作的简便性以及在无配体和无碱条件下的完全原子经济性。