2-(3-cyclohexylprop-1-ynyl)benzaldehyde | 1422392-08-2

• 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-(3-cyclohexylprop-1-ynyl)benzaldehyde
• 英文别名: 2-(3-Cyclohexylprop-1-ynyl)benzaldehyde
• CAS: 1422392-08-2
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: IYKQYEPMSYMEIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-cyclohexylprop-1-ynyl)benzaldehyde 在 4-二甲氨基吡啶 、 氯[2-(二叔丁基磷)二苯基]金 、 盐酸羟胺 、 N,N'-二环己基碳二亚胺 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成 10-(cyclohexylmethyl)-1-phenylpyrrolo[1,2-b]isoquinolin-3(5H)-one
  参考文献：
  名称：

  通过金（I）-催化的环化/烯炔环异构化/ 1,2-迁移级联反应合成吡咯并[1,2-b]异喹啉。

  摘要：

  开发了金（I）催化的N-炔基2-乙酰胺的级联转化，用于快速有效地合成吲哚并立定支架。通过顺序的亲核环化/烯炔环异构化/ 1,2-迁移过程，各种吡咯并[1,2- b]异喹啉在温和条件下以区域特异性和会聚的方式获得。在此过程中可以耐受各种烷基和芳基迁移基团。全面研究了迁移组的电子效应。对机理的研究表明，涉及金类胡萝卜素的途径是主要途径，并且烷基和芳基的1，2-迁移以分子内方式发生。该级联反应也被用作合成癸二烯B类似物的关键步骤。

  DOI：

  10.1021/acs.orglett.0c02310
• 作为产物：
  描述：

  3-环己基-1-丙炔 、 邻溴苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 、 copper(l) iodide 作用下， 反应 12.33h， 生成 2-(3-cyclohexylprop-1-ynyl)benzaldehyde
  参考文献：
  名称：

  Highly Selective Construction of Medium-Sized Lactams by Palladium-Catalyzed Intramolecular Hydroaminocarbonylation of Aminoalkynes

  摘要：

  A novel palladium-catalyzed intramolecular hydro-aminocarbonylation of aminoalkynes has been developed. This direct and operationally simple protocol provides a rapid and reliable approach to a diverse array of valuable seven- and eight-membered lactams with high chemoselectivity and regioselectivity. The high selectivity might be attributed to rational tuning the electronic nature of the amine moiety and the palladium catalyst, which enabled this transformation to proceed in the absence of acidic or any other additives under fairly mild reaction conditions. This method paves the way for the synthesis of medium-sized lactams.

  DOI：

  10.1021/acs.orglett.7b02284

文献信息

• Iodide-Catalyzed Halocyclization/Cycloaddition/Elimination Cascade Reaction
  作者：Ulrich Kloeckner、Peter Finkbeiner、Boris J. Nachtsheim

  DOI：10.1021/jo302676g

  日期：2013.3.15

  An iodocyclization reaction of o-alkynylphenyl carboxaldehydes is reported that is truly catalytic with respect to the electrophilic iodine source. With a combination of tetrabutylammonium iodide (TBAI), Oxone as non-nucleophilic and easy to handle co-oxidant, and fluorinated protic solvents, highly substituted 1-naphthalenones could be prepared in high yields of up to 91%.
• Synthesis of Pyrrolo[1,2-<i>b</i>]isoquinolines via Gold(I)-Catalyzed Cyclization/Enyne Cycloisomerization/1,2-Migration Cascade
  作者：Liangliang Song、Guilong Tian、Luc Van Meervelt、Erik V. Van der Eycken

  DOI：10.1021/acs.orglett.0c02310

  日期：2020.8.21

  of the migrating group is comprehensively investigated. The study of the mechanism indicates that the pathway involving a gold carbenoid species is the main pathway and that the 1,2-migration of alkyl and aryl groups to the gold carbenoid occurs in an intramolecular fashion. This cascade reaction is also employed as the key step for the synthesis of a decumbenine B analogue.

  开发了金（I）催化的N-炔基2-乙酰胺的级联转化，用于快速有效地合成吲哚并立定支架。通过顺序的亲核环化/烯炔环异构化/ 1,2-迁移过程，各种吡咯并[1,2- b]异喹啉在温和条件下以区域特异性和会聚的方式获得。在此过程中可以耐受各种烷基和芳基迁移基团。全面研究了迁移组的电子效应。对机理的研究表明，涉及金类胡萝卜素的途径是主要途径，并且烷基和芳基的1，2-迁移以分子内方式发生。该级联反应也被用作合成癸二烯B类似物的关键步骤。
• Highly Selective Construction of Medium-Sized Lactams by Palladium-Catalyzed Intramolecular Hydroaminocarbonylation of Aminoalkynes
  作者：Yue Hu、Hanmin Huang

  DOI：10.1021/acs.orglett.7b02284

  日期：2017.10.6

  A novel palladium-catalyzed intramolecular hydro-aminocarbonylation of aminoalkynes has been developed. This direct and operationally simple protocol provides a rapid and reliable approach to a diverse array of valuable seven- and eight-membered lactams with high chemoselectivity and regioselectivity. The high selectivity might be attributed to rational tuning the electronic nature of the amine moiety and the palladium catalyst, which enabled this transformation to proceed in the absence of acidic or any other additives under fairly mild reaction conditions. This method paves the way for the synthesis of medium-sized lactams.