ethyl 4-dimethylaminophenylpropiolate | 35283-11-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 4-dimethylaminophenylpropiolate
• 英文别名: ethyl p-dimethylaminophenylpropiolate；ethyl 3-(4-(dimethylamino)phenyl)；4-Dimethylaminophenyl-propinsaeureaethylester；(4-Dimethylamino-phenyl)-propynoic acid ethyl ester；ethyl 3-[4-(dimethylamino)phenyl]prop-2-ynoate
• CAS: 35283-11-5
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: KJELNXJBNUZEAN-UHFFFAOYSA-N

物化性质

• 熔点：
  36-38 °C
• 沸点：
  332.7±25.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-dimethylaminophenylpropiolate 、 苯甲脒 在 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以90%的产率得到2-Phenyl-4-(4-dimethylaminobenzylidene)imidazol-5-one
  参考文献：
  名称：

  A Phosphine-Catalyzed Preparation of 4-Arylidene-5-imidazolones

  摘要：

  A simple and efficient method for constructing 4-arylidene-S-imidazolones was developed using a phosphine-catalyzed tandem umpolung addition and intramolecular cyclization of amidine pronucleophiles on arylpropiolates. The reaction offers a robust route to heterocycle analogues of the fluorescent protein chromophores.

  DOI：

  10.1021/jo501922j
• 作为产物：
  描述：

  氯甲酸乙酯 、 4-(2-氯乙烯基)-N,N-二甲基苯胺 在 正丁基锂 作用下， 生成 ethyl 4-dimethylaminophenylpropiolate
  参考文献：
  名称：

  制备对二烷基氨基苯基乙炔的简便方法

  摘要：

  报道了两种制备对二烷基氨基苯乙炔的简便方法： a) 将二烷基氨基取代的肉桂酸在乙酸中而不是氯仿中容易地获得的溴化化合物脱溴化氢；b) 由对二甲氨基苯甲醛与氯亚甲基三苯基正膦反应得到的 2-氯苯乙烯衍生物的脱氯化氢。

  DOI：

  10.1246/bcsj.56.361

文献信息

• Novel Catalyst System for Hydrostannation of Alkynes
  作者：Sreya Gupta、Youngshil Do、Jin Hee Lee、Miryeong Lee、Junghoon Han、Young Ho Rhee、Jaiwook Park

  DOI：10.1002/chem.201303057

  日期：2014.1.27

  A catalyst system was developed for the highly regio‐ and stereoselective hydrostannation of a range of alkynes with tributylstannane under mild conditions. The active catalytic species was generated from a stable diruthenium complex by illuminating household fluorescent light (30 W) at room temperature.

  开发了一种催化剂体系，用于在温和条件下将一系列炔烃与三丁基锡烷进行高度区域和立体选择性加氢锡烷基化。活性催化物质是通过在室温下照射家用荧光灯（30 W）从稳定的钌络合物生成的。
• Phosphine-catalyzed cage carbon functionalization of o-carborane: facile synthesis of alkenylcarboranes
  作者：Fangrui Zheng、Tsz-Fai Leung、Ka-Wing Chan、Herman H. Y. Sung、Ian D. Williams、Zuowei Xie、Guochen Jia

  DOI：10.1039/c6cc05283e

  日期：——

  A phosphine-catalyzed alkenylation reaction of o-carborane with electron-deficient alkynes at the C-H vertex of o-carborane cage has been developed, which led to the preparation of a series of 1-alkenyl-o-carboranes in...

  已经开发了膦催化的邻碳硼烷与电子缺陷的炔烃在邻碳硼烷笼的CH顶点的链烯基化反应，从而导致了一系列1-烯基-邻碳硼烷的制备。
• Synthesis of pyrylium salts from trisubstituted 1,4-pentadiyn-3-ols with HClO4
  作者：Shin'ichi Nakatsuji、Kenichiro Nakashima、Kimiaki Yamamura、Shuzo Akiyama

  DOI：10.1016/s0040-4039(01)81547-1

  日期：1984.1

  The synthesis of 2,4,6-trisubstituted pyrylium salts from 1,3,5-trisubstituted 1,4-pentadiyn-3-ols with HClO4 is reported for the first time.

  首次报道了由1,3,5-三取代的1,4-戊二炔-3-醇与HClO 4合成2,4,6-三取代的吡啶鎓盐。
• Synthesis of α,β-Alkynyl Esters and Unsymmetrical Maleate Esters Catalyzed by Pd/C; An Efficient Phosphine-Free Catalytic System for Oxidative Alkoxycarbonylation of Terminal Alkynes
  作者：Bhalchandra Bhanage、Sandip Gadge

  DOI：10.1055/s-0032-1316896

  日期：——

  Pd/C-catalyzed oxidative alkoxycarbonylation of terminal alkynes using alcohols in the presence of tetrabutylammonium iodide under CO/O-2 (5:1 atm) has been investigated. The desired alpha,beta-alkynyl esters and unsymmetrical maleate esters are formed in good to excellent yields under different reaction conditions. The present protocol eliminates the use of phosphine ligands and has straightforward catalyst recovery. The catalyst was recycled up to six times without significant loss of catalytic activity.
• AKIYAMA, SHUZO;NAKATSUJI, SHINICHI;YOSHIDA, KEIKO;NAKASHIMA, KENICHIRO;HA+, BULL. CHEM. SOC. JAP., 1983, 56, N 1, 361-362
  作者：AKIYAMA, SHUZO、NAKATSUJI, SHINICHI、YOSHIDA, KEIKO、NAKASHIMA, KENICHIRO、HA+

  DOI：——

  日期：——