(4-Trifluoromethyl-phenyl)-propynoyl chloride | 152656-97-8

• 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: (4-Trifluoromethyl-phenyl)-propynoyl chloride
• CAS: 152656-97-8
• 化学式: C₁₀H₄ClF₃O
• 分子量: 232.589
• InChiKey: SKRWHQXNPRWQGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (4-Trifluoromethyl-phenyl)-propynoyl chloride 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 18.5h， 生成
  参考文献：
  名称：

  钯催化点轴手性转移开环反应合成联芳基和乙烯基芳基手性阻转异构体

  摘要：

  报道了钯催化的 8 H-茚并[1,2 - c ]噻吩-8-醇和N- (2-溴苯基)丙酰胺衍生物之间的多米诺环化/开环反应。该反应具有高度立体有择的点手性到轴手性的转移过程，使得只有一个手性中心的化合物能够合成含有两个手性轴的分子。

  DOI：

  10.1021/acs.orglett.2c03760
• 作为产物：
  描述：

  4-碘三氟甲苯 在 四(三苯基膦)钯 、 氯化亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 15.0h， 生成 (4-Trifluoromethyl-phenyl)-propynoyl chloride
  参考文献：
  名称：

  钯催化点轴手性转移开环反应合成联芳基和乙烯基芳基手性阻转异构体

  摘要：

  报道了钯催化的 8 H-茚并[1,2 - c ]噻吩-8-醇和N- (2-溴苯基)丙酰胺衍生物之间的多米诺环化/开环反应。该反应具有高度立体有择的点手性到轴手性的转移过程，使得只有一个手性中心的化合物能够合成含有两个手性轴的分子。

  DOI：

  10.1021/acs.orglett.2c03760

文献信息

• Carbene-catalyzed LUMO activation of alkyne esters for access to functional pyridines
  作者：Chengli Mou、Jichang Wu、Zhijian Huang、Jun Sun、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1039/c7cc08039e

  日期：——

  A carbene-catalyzed LUMO activation of α,β-unsaturated alkyne esters is reported. This catalytic process allows for effective reactions of alkyne esters with enamides to synthesize functional pyridines via simple protocols. A previously unexplored unsaturated alkyne acyl azolium intermediate is involved in the key step of the reaction.

  报道了卡宾催化的α，β-不饱和炔烃的LUMO活化。该催化过程允许炔烃酯与烯酰胺的有效反应，以通过简单的方案合成功能性吡啶。反应的关键步骤涉及先前未开发的不饱和炔烃酰基偶氮中间体。
• Pd-Catalyzed Enantioselective Desymmetrizing 1,7-Enyne Cycloisomerization of Alkyne-Tethered Cyclopentenes
  作者：Ren-Xiao Liang、Chao Ding、Hu-Jie Cai、Jia-Yi Wang、Qi-Chuang Li、Gao-Yang Yu、Yi-Xia Jia

  DOI：10.1021/acs.orglett.4c01507

  日期：2024.5.24

  An enantioselective Pd-catalyzed intramolecular desymmetrizing cycloisomerization of N-(cyclopent-3-en-1-yl)propiolamides has been developed by employing a new chiral phosphoramidite ligand. A series of structurally unique bridged azabicycles are achieved in moderate to excellent yields with good E/Z selectivity and high enantioselectivity. Synthetic transformations are conducted to demonstrate the

  通过采用新的手性亚磷酰胺配体，开发了N- (环戊-3-en-1-基)丙酰胺的对映选择性 Pd 催化分子内去对称环异构化。一系列结构独特的桥联氮杂双环化合物以中等至优异的产率获得，并具有良好的E / Z选择性和高对映选择性。进行合成转化以证明该反应的实际用途。
• 2,5-Diarylisothiazolone: novel inhibitors of cytokine-induced cartilage destruction
  作者：Stephen W. Wright、Joseph J. Petraitis、Bruce Freimark、John V. Giannaras、Michael A. Pratta、Susan R. Sherk、Jean M. Williams、Ronald L. Magolda、Elizabeth C. Arner

  DOI：10.1016/0968-0896(96)00053-3

  日期：1996.6

  A series of 2,5-diarylisothiazolones is reported that inhibit the IL-lp-induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, nonpeptide lead series approach to the mediation of the chronic cartilage breakdown associated with arthritic disease. These compounds are relatively resistant to reductive metabolism by liver microsomal preparations and appear to inhibit cartilage breakdown by interfering with the proteolytic activation of matrix metalloproteinases. Copyright (C) 1996 Elsevier Science Ltd
• Convergent and Rapid Assembly of Substituted 2-Pyridones through Formation of <i>N</i>-Alkenyl Alkynylamides Followed by Gold-Catalyzed Cycloisomerization
  作者：Hidetomo Imase、Keiichi Noguchi、Masao Hirano、Ken Tanaka

  DOI：10.1021/ol801466f

  日期：2008.8.21

  A new method for the convergent and rapid assembly of substituted 2-pyridones was developed through the formation of N-alkenyl alkynylamides (amide-linked 1,5-enynes) by N-acylation of imines with alkynoyl chlorides and the subsequent cationic Au(I)/PPh3-catalyzed cycloisomerization.
• Gold-Catalyzed Cyclization and Subsequent Arylidene Group Transfer of <i>O</i>-Propioloyl Oximes
  作者：Itaru Nakamura、Masashi Okamoto、Masahiro Terada

  DOI：10.1021/ol100581m

  日期：2010.6.4

  Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 degrees C in the presence of Au(PPh(3))NTf(2) (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.