3,5-Dichloro-2-(3-phenylprop-2-ynoxy)benzaldehyde | 1286745-78-5

• 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: 3,5-Dichloro-2-(3-phenylprop-2-ynoxy)benzaldehyde
• CAS: 1286745-78-5
• 化学式: C₁₆H₁₀Cl₂O₂
• 分子量: 305.16
• InChiKey: OFNCIYMPJXVIGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-Dichloro-2-(3-phenylprop-2-ynoxy)benzaldehyde 在 3,5-dibromopyridinium triflate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以92%的产率得到(6,8-dichloro-2H-chromen-3-yl)(phenyl)methanone
  参考文献：
  名称：

  三氟甲基吡啶鎓催化O-丙基化2-羟基芳基醛的分子内炔烃羰基复分解反应

  摘要：

  3,5-二溴pri鎓三氟甲磺酸盐催化各种O-炔丙基化的2-羟基芳基醛和带有烷基，芳基和杂芳基取代的内部炔烃的分子的内炔-羰基复分解反应，从而在高浓度下提供各种3-（杂）芳酰基2 H-色烯产量。

  DOI：

  10.1016/j.tetlet.2020.152657
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 在 三溴化磷 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 3,5-Dichloro-2-(3-phenylprop-2-ynoxy)benzaldehyde
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of Functionalized 2H-Chromenes via Intramolecular Alkyne−Carbonyl Metathesis

  摘要：

  An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, brow, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.

  DOI：

  10.1021/jo2000012

文献信息

• Gold(I)-Catalyzed Cycloisomerization of <i>ortho</i> -(Propargyloxy)arenemethylenecyclopropanes Controlled by Adjacent Substituents at Aromatic Rings
  作者：Wei Fang、Yin Wei、Xiang-Ying Tang、Min Shi

  DOI：10.1002/chem.201700600

  日期：2017.5.17

  Gold(I)‐catalyzed cycloisomerization of ortho‐(propargyloxy)arenemethylenecyclopropanes afforded two different types of products, that is, products of methylenecyclopropane migration and cycloisomerization products of the methylenecyclopropane moiety, controlled jointly by electronic and steric effects of the adjacent substituents. Furthermore, the corresponding cycloisomerization products could be

  金（I）催化的邻-（炔丙基氧基）亚芳基亚甲基环丙烷的环异构化提供了两种不同类型的产物，即亚甲基环丙烷迁移的产物和亚甲基环丙烷部分的环异构化产物，受相邻取代基的电子和空间效应共同控制。此外，相应的环异构化产物也可以以对映异构体富集的方式产生。
• Catalytic Cycloisomerization of Enyne Diesters Derived From 2‐Propargyloxyarylaldehydes
  作者：Manoj Kumar Saini、Shashi Kant Verma、Ashok K Basak

  DOI：10.1002/adsc.202200026

  日期：2022.3.15

  A catalytic cycloisomerization of enyne diesters derived from 2-propargyloxyarylaldehydes is described. The cycloisomerization, catalyzed by 10 mol% In(OTf)3, provides access to 2H-chromenes bearing diethyl 2-(hetero)arylidene malonates at 3-position. This enyne metathesis-type reaction is also useful for the synthesis of thia-, aza- and quinoline analogs of the 3-substituted 2H-chromenes. DDQ mediated

  描述了衍生自 2-炔丙基氧基芳醛的烯炔二酯的催化环化异构化。由 10 mol% In(OTf) 3催化的环异构化提供了在 3 位上带有 2-(杂)亚芳基丙二酸二乙酯的2 H-色烯的途径。这种烯炔复分解型反应也可用于合成 3-取代的 2 H-色烯的硫杂、氮杂和喹啉类似物。DDQ 介导的氧化 C-N 键形成和进一步的合成操作能够将 3-取代的 2 H-色烯转化为色烯融合的分子支架。Pd(0) 催化的分子内 Heck 反应在适当取代的 2 H-色烯上提供了基于茚的分子支架。
• Boron trifluoride–etherate in fluorinated alcohols: A powerful promoter system for intramolecular alkyne–aldehyde metathesis of o-(3-arylpropargyloxy)benzaldehydes
  作者：Arup Jyoti Das、Runjun Devi、Sajal Kumar Das

  DOI：10.1016/j.tetlet.2018.10.040

  日期：2018.11

  Boron trifluoride-etherate (BF3 center dot OEt2) in 2,2,2-trifluoroethanol (TFE) was found to be a highly efficient promoter system for the intramolecular alkyne-aldehyde metathesis of o-(3-arylpropargyloxy)benzaldehydes. The reaction produces the corresponding 3-aroyl-2H-chromenes in excellent yields under metal free conditions. (C) 2018 Elsevier Ltd. All rights reserved.
• Pyridinium triflate catalyzed intramolecular alkyne-carbonyl metathesis reaction of O-propargylated 2-hydroxyarylaldehydes
  作者：Manoj Kumar Saini、Harshita Singh Korawat、Shashi Kant Verma、Ashok K. Basak

  DOI：10.1016/j.tetlet.2020.152657

  日期：2020.12

  3,5-Dibromopridinium trifluoromethanesulfonate catalyzes the intramolecular alkyne-carbonyl metathesis reaction of a variety of O-propargylated 2-hydroxyarylaldehydes and ketones bearing alkyl, aryl and heteroaryl substituted internal alkynes to provide various 3-(hetero)aroyl 2H-chromenes in high yields.

  3,5-二溴pri鎓三氟甲磺酸盐催化各种O-炔丙基化的2-羟基芳基醛和带有烷基，芳基和杂芳基取代的内部炔烃的分子的内炔-羰基复分解反应，从而在高浓度下提供各种3-（杂）芳酰基2 H-色烯产量。
• Iron-Catalyzed Synthesis of Functionalized 2<i>H</i>-Chromenes via Intramolecular Alkyne−Carbonyl Metathesis
  作者：Krishnendu Bera、Soumen Sarkar、Srijit Biswas、Sukhendu Maiti、Umasish Jana

  DOI：10.1021/jo2000012

  日期：2011.5.6

  An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, brow, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.