2-(cyclohex-1-en-1-ylethynyl)-N,N-dimethylaniline

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(cyclohex-1-en-1-ylethynyl)-N,N-dimethylaniline
• 英文别名: N,N-dimethyl-2-(cyclohex-1-enylethynyl)aniline；2-[2-(cyclohexen-1-yl)ethynyl]-N,N-dimethylaniline
• 化学式: C₁₆H₁₉N
• 分子量: 225.334
• InChiKey: KWSHQGMBCAWMLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(cyclohex-1-en-1-ylethynyl)-N,N-dimethylaniline 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到N-methyl-2-(cyclohex-1-enyl)-3-iodoindole
  参考文献：
  名称：

  Synthesis of 3-Iodoindoles by Electrophilic Cyclization of N,N-Dialkyl-2-(1-alkynyl)anilines

  摘要：

  A wide variety of N-alkyl-3-iodoindoles are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization by I-2. Alkyl-, aryl-, and vinylic-substituted alkynes all undergo iodocyclization in excellent yields.

  DOI：

  10.1021/ol0498996
• 作为产物：
  描述：

  1-乙炔基环己烷 、 邻碘-N,N-二甲基苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 6.0h， 以87%的产率得到2-(cyclohex-1-en-1-ylethynyl)-N,N-dimethylaniline
  参考文献：
  名称：

  通过 N,N-二烷基-2-碘苯胺和末端炔烃的 Pd/Cu 催化偶联合成 3-亚硫基-和 3-硒基吲哚，然后进行 n-Bu4NI 诱导的亲电环化

  摘要：

  3-亚硫基-和 3-硒基吲哚可通过两步法合成，包括钯/铜催化的N , N - 二烷基-邻 -碘苯胺和末端炔烃的交叉偶联以及随后所得N , N - 的亲电环化二烷基-邻-(1-炔基)苯胺与芳基硫基氯或芳基硒基氯。存在化学计量的n -Bu 4NI 对于亲电环化的成功至关重要。各种带有烷基、乙烯基、芳基和杂芳基取代基的 3-亚苯基和 3-硒基吲哚衍生物已经以良好到极好的产率（高达 99%）制备。通过使用N，N-二苄基-邻-碘苯胺，已成功制备了3-硫基-N - H-吲哚。此外，3-磺酰基-和3-亚磺酰基吲哚也已通过相应的3-亚磺酰基吲哚的轻松氧化成功制备。

  DOI：

  10.1021/jo9014003

文献信息

• Palladium(II)-Catalyzed Tandem Cyclization/C–H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
  作者：Xiao-Feng Xia、Ning Wang、Lu−Lu Zhang、Xian-Rong Song、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/jo301741j

  日期：2012.10.19

  A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.
• A Novel Synthetic Route to 3-Sulfenyl- and 3-Selenylindoles by <i>n</i>-Bu₄NI-Induced Electrophilic Cyclization
  作者：Yu Chen、Chul-Hee Cho、Richard C. Larock

  DOI：10.1021/ol8021287

  日期：2009.1.1

  3-Sulfenyl- and 3-selenylindoles are prepared In excellent yields by the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization with arylsulfenyl chlorides and arylselenyl chlorides in the presence of a stoichiometric amount of n-Bu4NI.
• Synthesis of 3-Iodoindoles by the Pd/Cu-Catalyzed Coupling of <i>N,N</i>-Dialkyl-2-iodoanilines and Terminal Acetylenes, Followed by Electrophilic Cyclization
  作者：Dawei Yue、Tuanli Yao、Richard C. Larock

  DOI：10.1021/jo051549p

  日期：2006.1.1

  3-lodoindoles have been prepared in excellent yields by coupling terminal acetylenes with N,N-dialkyl-o-iodoanilines in the presence of a Pd/Cu catalyst, followed by an electrophilic cyclization of the resulting N,N-dialkyl-o-(1-alkynyl)anilines using I-2 in CH2Cl2. Aryl-, vinylic-, alkyl-, and silyl-substituted terminal acetylenes undergo this process to produce excellent yields of 3-iodoindoles. The reactivity of the carbon-nitrogen bond cleavage during cyclization follows the following order: Me > n-Bu, Me > Ph, and cyclohexyl > Me. Subsequent palladium-catalyzed.Sonogashira, Suzuki, and Heck reactions of the resulting 3-iodoindoles proceed smoothly in good yields.
• An efficient, microwave-assisted, one-pot synthesis of indoles under Sonogashira conditions
  作者：Yu Chen、Nataliya A. Markina、Richard C. Larock

  DOI：10.1016/j.tet.2009.07.075

  日期：2009.10

  A microwave-assisted, one-pot, three-component coupling reaction for the synthesis of indoles has been developed. The reaction is carried out in two steps under standard Sonogashira coupling conditions from an N-substituted/N,N-disubstituted 2-iodoaniline and a terminal alkyne, followed by the addition of acetonitrile and an aryl iodide. A variety of polysubstituted indoles have been prepared in moderate to excellent yields using the present method. (C) 2009 Elsevier Ltd. All rights reserved.