N,N-dimethyl-4-(4-phenylbuta-1,3-diyn-1-yl)aniline | 638216-82-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-4-(4-phenylbuta-1,3-diyn-1-yl)aniline
• 英文别名: N,N-dimethyl-4-(phenylbuta-1,3-diyn-1-yl)aniline；4-N,N-dimethylaminophenyl[butadiynyl]benzene；N,N-dimethyl-4-(4-phenylbuta-1,3-diynyl)aniline
• CAS: 638216-82-7
• 化学式: C₁₈H₁₅N
• 分子量: 245.324
• InChiKey: HDNNMWNQYWCMIN-UHFFFAOYSA-N

物化性质

• 熔点：
  113 °C(Solv: ethyl ether (60-29-7); pentane (109-66-0))
• 沸点：
  398.0±34.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  7,7,8,8-四氰基对苯二醌二甲烷 、 N,N-dimethyl-4-(4-phenylbuta-1,3-diyn-1-yl)aniline 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以72%的产率得到[1-{[4-(dicyanomethylene)cyclohexa-2,5-dien-1-ylidene][4-(dimethylamino)phenyl]-methyl}-3-phenylprop-2-yn-1-ylidene]malononitrile
  参考文献：
  名称：

  A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2 + 2] cycloaddition with alkynes

  摘要：

  通过7,7,8,8-四氰基喹喔啉（TCNQ）与N,N-二烷基苯胺取代的（DAA取代的）炔烃之间的区域选择性[2 + 2]环加成反应，随后对初始形成的环丁烯进行环开裂，制备了一系列具有强烈低能内分子电荷转移带的供-受体分子。

  DOI：

  10.1039/b713683h
• 作为产物：
  描述：

  4-二甲基氨基苯乙炔 在 正丁基锂 、 盐酸羟胺 、 乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N,N-dimethyl-4-(4-phenylbuta-1,3-diyn-1-yl)aniline
  参考文献：
  名称：

  合成，结构，电子性质和丁二的热行为取代phenylCr（CO）3个-complexes

  摘要：

  丁二取代的η 6 -benzeneCr（CO）3个配合物3是由催化的铜的苯乙炔络合物的耦合非常有效地制备1个溴炔2。的电子效应通过丁二桥的发送通过共振机制操作为通过相关哈米特之间建立σ p，σ [R和σ P +参数。然而，最有趣的是，异常的热行为导致了结构未知的难处理的顺磁性聚合物。根据热分析（热重量分析，差示扫描量热法），配合物3在CO挤出下以热固态反应进行反应，从而得到无定形的交联聚合物。

  DOI：

  10.1016/s0022-328x(03)00708-3

文献信息

• Visible-light-activated copper(<scp>i</scp>) catalyzed oxidative C_sp–C_sp cross-coupling reaction: efficient synthesis of unsymmetrical conjugated diynes without ligands and base
  作者：Arunachalam Sagadevan、Ping-Chiang Lyu、Kuo Chu Hwang

  DOI：10.1039/c6gc01463a

  日期：——

  A novel visible-light-promoted copper-catalysed process for highly selective Csp-Csp cross-coupling reaction of terminal alkynes at room temperature is described. The current photochemical method is simple, high functional group compatible, and...

  描述了一种新型的可见光促进的铜催化的炔烃在室温下高度选择性的Csp-Csp交叉偶联反应的方法。当前的光化学方法简单，具有高官能团相容性，并且...
• One‐pot synthesis of unsymmetrical 1,3‐butadiyne derivatives
  作者：Zhicai Zhao

  DOI：10.1002/bkcs.12762

  日期：2023.10

  An efficient co-operative Ni/Cu system for Cadiot–Chodkiewicz coupling utilizes CaC2 as the alkyne source. The advantage of this cross-coupling reaction lies in the low cost of using cheap and readily available raw materials and the simplicity of operation. A series of functionalized diaryl, aryl-alkyl, and aryl-heteroaryl 1,3-diynes are obtained in moderate to high yields.

  Cadiot-Chodkiewicz 耦合的高效协同 Ni/Cu 系统利用 CaC 2作为炔烃源。这种交叉偶联反应的优点在于使用廉价易得的原材料成本低且操作简单。以中等到高产率获得了一系列官能化二芳基、芳基-烷基和芳基-杂芳基1,3-二炔。
• Nonafluorobutanesulfonyl Azide as a Shelf-Stable Highly Reactive Oxidant for the Copper-Catalyzed Synthesis of 1,3-Diynes from Terminal Alkynes
  作者：José Ramón Suárez、Daniel Collado-Sanz、Diego J. Cárdenas、Jose Luis Chiara

  DOI：10.1021/jo5025909

  日期：2015.1.16

  Nonafluorobutanesulfonyl azide is a highly efficient reagent for the copper-catalyzed coupling of terminal alkynes to give symmetrical and unsymmetrical 1,3-diynes in good to excellent yields and with good functional group compatibility. The reaction is extremely fast (<10 min), even at low temperature (-78 degrees C), and requires substoichiometric amounts of a simple copper(I) or copper(II) salt (2-5 mol %) and an organic base (0.6 mol %). A possible mechanistic pathway is briefly discussed on the basis of model DFT theoretical calculations. The quantitative assessment of the safety of use and shelf stability of nonafluorobutanesulfonyl azide has confirmed that this reagent is a superior and safe alternative to other electrophilic azide reagents in use today.
• Deciphering the Photophysical Role of Conjugated Diyne in Butadiynyl Fluorophores: Synthesis, Photophysical and Theoretical Study
  作者：Avik Kumar Pati、Monalisa Mohapatra、Pokhraj Ghosh、Santosh J. Gharpure、Ashok K. Mishra

  DOI：10.1021/jp404809g

  日期：2013.8.1

  The present work focuses on the current interest in diyne bridged chromophores necessitating a clearer understanding of the photophysics of such molecules. The significance of the diyne moiety in the photophysics has been investigated by synthesizing simple substituted diphenyl butadiynyl derivatives following a quick and efficient microwave assisted Eglinton coupling of terminal alkynes. Emission of the fluorophores is observed from the usual locally excited (LE) state and intramolecular charge transfer (ICT) state. Separation of pure ICT emission from pure LE emission has been carried out by Gaussian/Lorentzian curve fitting. The vibronic coupling in the local transitions appears to be confined to the normal mode involving the C-C triple bond stretching of the diyne moiety. This implies that the LE transition involves the diyne moiety, a conclusion supported by quantum chemical calculations. The resolved ICT emission follows double linear dependence on E-T(30) solvent polarity scale. The important role of the diyne moiety in the photophysics of this class of molecules is clearly discernible in this study.