N-cyclohexyl-N-methyl-[3-(4-methoxyphenyl)-2-propynyl]amine | 1025731-91-2

• 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: N-cyclohexyl-N-methyl-[3-(4-methoxyphenyl)-2-propynyl]amine
• 英文别名: N-methyl-N-(3-(4-methylphenyl)prop-2-yn-1-yl)cyclohexanamine；N-methyl-N-(3-(p-tolyl)prop-2-yn-1-yl)cyclohexanamine；N-methyl-N-(3-p-tolylprop-2-ynyl)cyclohexanamine；N-methyl-N-[3-(4-methylphenyl)prop-2-ynyl]cyclohexanamine
• CAS: 1025731-91-2
• 化学式: C₁₇H₂₃N
• 分子量: 241.376
• InChiKey: NCLRCWSZDQVPNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,N-二甲基环己胺 、 4-甲苯基乙炔 在 氧气 、 zinc dibromide 作用下， 100.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以79%的产率得到N-cyclohexyl-N-methyl-[3-(4-methoxyphenyl)-2-propynyl]amine
  参考文献：
  名称：

  通过将锌的组合的催化剂末端炔胺和叔胺的需氧交叉脱氢偶联2+和OMS-2 †

  摘要：

  在ZnBr 2和基于锰氧化物的八面体分子筛（OMS-2）的存在下，使用分子氧作为末端氧化剂，有效地进行了多种末端炔烃和叔胺与炔丙基胺的交叉脱氢偶联。

  DOI：

  10.1039/c4ra05105j

文献信息

• Efficient synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines over silver catalysts
  作者：Xiuling Chen、Tieqiao Chen、Yongbo Zhou、Chak-Tong Au、Li-Biao Han、Shuang-Feng Yin

  DOI：10.1039/c3ob41878b

  日期：——

  A simple, efficient and highly functional group compatible method for the synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines using silver catalysts has been developed.

  开发了一种简单、高效且功能性强的群兼容方法，用于以银催化剂从末端炔烃、二氯甲烷和叔胺合成炔丙胺。
• Functionalization of aliphatic tertiary amines mediated by hexachloroethane/cat. copper: synthesis of propargylic amines and methylene-bridged bis-1,3-dicarbonyl derivatives
  作者：Xiaoliang Xu、Zhichuang Ge、Dongping Cheng、Xiaonian Li

  DOI：10.3998/ark.5550190.0013.810

  日期：——

  Copper-catalyzed functionalization of aliphatic tertiary amines with the assistance of C2Cl6 is described. This method details the alkynylation of aliphatic tertiary amines and the synthesis of methylene-bridged bis-1,3-dicarbonyl derivatives. The mechanism of the selective oxidation of aliphatic tertiary amines was also discussed. A broad spectrum of aliphatic tertiary amines was examined in this

  描述了在 C2Cl6 的帮助下铜催化的脂肪族叔胺官能化。该方法详细介绍了脂肪族叔胺的炔基化和亚甲基桥联双-1,3-二羰基衍生物的合成。还讨论了脂肪族叔胺的选择性氧化机理。在该方法中检查了广谱的脂肪族叔胺。
• Copper-Catalyzed Coupling of Tertiary Aliphatic Amines with Terminal Alkynes to Propargylamines via C−H Activation
  作者：Mingyu Niu、Zhengming Yin、Hua Fu、Yuyang Jiang、Yufen Zhao

  DOI：10.1021/jo800279j

  日期：2008.5.1

  convenient and efficient method for coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C−H activation. The protocol uses CuBr as the catalyst, NBS as the free radical initiator, CH3CN as the solvent, and the alkynylation was selectively performed on the methyl of tertiary aliphatic amines at 80 °C. This is an economical and practical method for the synthesis of propargylamines

  我们已经开发了一种方便高效的方法，用于通过CH活化将末端脂肪族叔脂肪胺与炔丙基胺偶联。该方案使用CuBr作为催化剂，NBS作为自由基引发剂，CH 3 CN作为溶剂，并在80°C的条件下对脂肪族叔胺的甲基进行了烷基化反应。这是合成炔丙基胺的经济实用的方法。
• Aerobic cross-dehydrogenative coupling of terminal alkynes and tertiary amines by a combined catalyst of Zn²⁺and OMS-2
  作者：Xiongjie Jin、Kazuya Yamaguchi、Noritaka Mizuno

  DOI：10.1039/c4ra05105j

  日期：——

  In the presence of ZnBr2 and a manganese oxide-based octahedral molecular sieve (OMS-2), cross-dehydrogenative coupling of a wide range of terminal alkynes and tertiary amines to propargylamines efficiently proceeded using molecular oxygen as the terminal oxidant.

  在ZnBr 2和基于锰氧化物的八面体分子筛（OMS-2）的存在下，使用分子氧作为末端氧化剂，有效地进行了多种末端炔烃和叔胺与炔丙基胺的交叉脱氢偶联。
• Copper/Diethyl Azodicarboxylate Mediated Regioselective Alkynylation of Unactivated Aliphatic Tertiary Methylamine with Terminal Alkyne
  作者：Xiaoliang Xu、Xiaonian Li

  DOI：10.1021/ol802974b

  日期：2009.2.19

  Mediated by copper/diethyl azodicarboxylate, regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne was successfully established. It is not necessary for the tertiary methylamines to be aryl substituted to modulate the properties of amines. The alkynylation reaction described here has the advantage of simple operation, mild reaction conditions, good to excellent yields, and no need to exclude air and moisture.