2-(2-(2-(trifluoromethyl)phenyl)ethynyl)benzaldehyde | 1257247-26-9

• 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: 2-(2-(2-(trifluoromethyl)phenyl)ethynyl)benzaldehyde
• 英文别名: 2-((2-(trifluoromethyl)phenyl)-ethynyl)benzaldehyde；2-[2-[2-(Trifluoromethyl)phenyl]ethynyl]benzaldehyde
• CAS: 1257247-26-9
• 化学式: C₁₆H₉F₃O
• 分子量: 274.242
• InChiKey: DMLQMPFMNYUWBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(2-(trifluoromethyl)phenyl)ethynyl)benzaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 7.0h， 以94%的产率得到3-[[2-(trifluoromethyl)phenyl]methylidene]-2-benzofuran-1-one
  参考文献：
  名称：

  One-pot synthesis of phthalides via regioselective intramolecular cyclization from ortho-alkynylbenzaldehydes

  摘要：

  A one-pot synthesis of phthalides via an intramolecular 5-exo-dig cyclization of ortho-alkynylbenzaldehydes under mild NaClO2 oxidation conditions is described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.023
• 作为产物：
  描述：

  2-乙炔基-α,α,α-三氟甲苯 、 邻溴苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以85%的产率得到2-(2-(2-(trifluoromethyl)phenyl)ethynyl)benzaldehyde
  参考文献：
  名称：

  Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of ortho-Alkynylbenzaldehydes: An Entry to Functionalized Isochromene Derivatives

  摘要：

  A Ag-catalyzed versatile and efficient access to 1H,1-arylisochromenes is reported. Starting from ortho-alkynylbenzaldehydes bearing various substitution patterns on the benzaldehyde and alkynyl units, the use of silver triflate (10 mol %) allowed a domino hydroarylation/cycloisomerization reaction process, leading to aryl-functionalized 1H-isochromene (>10 compounds, 80-98% yields). Notably, the reaction conditions were also compatible with benzaldehydes bearing an aliphatic-substituted alkynyl moiety with modest to good yields (34-88%, 10 compounds).

  DOI：

  10.1021/ol5021256

文献信息

• Transition-metal-free approaches to 2,3-diarylated indenones from 2-alkynylbenzaldehydes and phenols with tunable selectivity
  作者：Tuanli Yao、Shuaijing Zhao、Tao Liu、Yuting Wu、Yanhui Ma、Tao Li、Xiangyang Qin

  DOI：10.1039/d2cc01324j

  日期：——

  The first transition-metal-free synthesis of 2,3-diarylindenones with tunable selectivity via tandem annulation of 2-alkynylbenzaldehydes with phenols has been developed.

  通过2-炔基苯甲醛与酚的串联环化反应，开发出了第一个无过渡金属合成2,3-二芳基茚酮的方法，其选择性可调。
• Synthesis of 3-aminoindenes and <i>cis</i>-1-aminoindanes by Zn(OTf)₂-catalyzed cyclization of <i>o</i>-alkynylbenzaldehydes with tertiary alkyl primary amines
  作者：Tuanli Yao、Rui Zhu、Tao Liu

  DOI：10.1039/d3cc04180h

  日期：——

  Using Zn(OTf)2 as catalyst, a highly regio- and chemo-selective cyclocarboamination of o-alkynylbenzaldehydes with tertiary alkyl primary amines was realized to access 3-aminoindenes with different substitution patterns from previously reported methods. The full reduction of the iminoindenone intermediates affords cis-1-amino-2-arylindanes with excellent diastereoselectivity. Mechanistically, the reaction

  使用Zn(OTf) 2作为催化剂，实现了邻炔基苯甲醛与叔烷基伯胺的高度区域和化学选择性环碳胺化，从而获得具有与先前报道的方法不同的取代模式的3-氨基茚。亚氨基茚酮中间体的完全还原提供了具有优异非对映选择性的顺式-1-氨基-2-芳基茚满。从机理上讲，该反应涉及 1-氨基-3-亚芳基-异吲哚啉的重排和 1-氨基茚异构化为 3-氨基茚。
• Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of <i>ortho</i>-Alkynylbenzaldehydes: An Entry to Functionalized Isochromene Derivatives
  作者：Gaëlle Mariaule、Gregory Newsome、Patrick Y. Toullec、Philippe Belmont、Véronique Michelet

  DOI：10.1021/ol5021256

  日期：2014.9.5

  A Ag-catalyzed versatile and efficient access to 1H,1-arylisochromenes is reported. Starting from ortho-alkynylbenzaldehydes bearing various substitution patterns on the benzaldehyde and alkynyl units, the use of silver triflate (10 mol %) allowed a domino hydroarylation/cycloisomerization reaction process, leading to aryl-functionalized 1H-isochromene (>10 compounds, 80-98% yields). Notably, the reaction conditions were also compatible with benzaldehydes bearing an aliphatic-substituted alkynyl moiety with modest to good yields (34-88%, 10 compounds).
• One-pot synthesis of phthalides via regioselective intramolecular cyclization from ortho-alkynylbenzaldehydes
  作者：Jim Li、Elbert Chin、Alfred S. Lui、Lijing Chen

  DOI：10.1016/j.tetlet.2010.09.023

  日期：2010.11

  A one-pot synthesis of phthalides via an intramolecular 5-exo-dig cyclization of ortho-alkynylbenzaldehydes under mild NaClO2 oxidation conditions is described. (C) 2010 Elsevier Ltd. All rights reserved.