Ethyl 2-cyano-3-(4-propan-2-ylphenyl)prop-2-enoate | 2286-34-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Ethyl 2-cyano-3-(4-propan-2-ylphenyl)prop-2-enoate
• CAS: 2286-34-2
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: TZDDDADGOBQFAK-UHFFFAOYSA-N

物化性质

• 沸点：
  367.0±30.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-cyano-3-(4-propan-2-ylphenyl)prop-2-enoate 在 硫酸 、 magnesium 、 溶剂黄146 作用下， 反应 24.5h， 生成 3-(4-Fluoro-phenyl)-3-(4-isopropyl-phenyl)-propionic acid
  参考文献：
  名称：

  Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

  摘要：

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.

  DOI：

  10.1021/jm00361a002
• 作为产物：
  描述：

  氰乙酸乙酯 、 4-异丙基苯甲醛 在 mesoporous carbon nitride 作用下， 以 甲苯 为溶剂， 反应 0.2h， 以78.1%的产率得到Ethyl 2-cyano-3-(4-propan-2-ylphenyl)prop-2-enoate
  参考文献：
  名称：

  介孔氮化碳作为微波辅助氰基乙酸乙酯与芳族醛的Knoevenagel缩合反应中的无金属碱催化剂

  摘要：

  合成并研究了高氮含量的中孔氮化碳（MCN），作为氰基乙酸乙酯与芳族醛的Knoevenagel缩合的无金属基础催化剂。发现该催化剂对于在微波辐射下进行的Knoevenagel缩合是有效的。在12分钟的短时间内获得的产量在75–95％的范围内。介孔氮化碳易于回收并重复使用多达5个循环，而不会降低催化活性。

  DOI：

  10.1016/j.cattod.2011.07.024

文献信息

• Imidazolium chloride immobilized SBA-15 as a heterogenized organocatalyst for solvent free Knoevenagel condensation using microwave
  作者：Mst. Nargis Parvin、Hua Jin、Mohd. Bismillah Ansari、Soon-Moon Oh、Sang-Eon Park

  DOI：10.1016/j.apcata.2011.11.008

  日期：2012.1

  short channeled disk type mesostructure which can provide facile to-and-from diffusion of substrates and products with enhanced activity. This heterogenized organocatalyst ILS had been investigated for the Knoevenagel condensation reaction of different aromatic and heteroaromatic aldehyde with ethyl cyanoacetate in solvent free conditions. The catalyst ILS was found to be efficient to catalyze the condensation

  通过微波辐射共缩聚法合成1-甲基-3-[（3-三乙氧基甲硅烷基）丙基]咪唑鎓氯化物[MTESPImCl]固定化的非均相有机催化剂，其中1-甲基咪唑（Im）被改性有机硅烷（3-氯丙基三乙氧基硅烷）。ILS的特征是小天使XRD，N 2吸附解吸等温线，TEM，SEM，TGA和FT-IR。ILS显示2D六角形短通道盘状介观结构，可以提供增强的活性，可以轻松地在基材和产品之间来回扩散。已经研究了这种均相的有机催化剂ILS在无溶剂条件下用于不同芳族和杂芳族醛与氰基乙酸乙酯的Knoevenagel缩合反应。发现使用单模微波辐射，催化剂ILS可有效催化缩合，从而有效地导致反应在6分钟内完成。
• Synthesis of Polysubstituted Dihydropyridines by Four-Component Reactions of Aromatic Aldehydes, Malononitrile, Arylamines, and Acetylenedicarboxylate
  作者：Jing Sun、Er-Yan Xia、Qun Wu、Chao-Guo Yan

  DOI：10.1021/ol101475b

  日期：2010.8.20

  procedure for the preparation of the polysubstituted dihydropyridines was developed through a unique four-component reaction of aromatic aldehydes, malononitrile, arylamines, and acetylenedicarboxylate in ethanol in the presence of triethylamine as a base promoter. This four-component reaction is atom-efficient, high-yielding, and applicable to a wide variety of four-component reactions.

  在三乙胺作为碱助催化剂的存在下，通过芳族醛，丙二腈，芳基胺和乙炔二羧酸酯在乙醇中的独特的四组分反应，开发了一种制备多取代的二氢吡啶的实用有效的方法。该四组分反应是原子有效的，高产率的，并且适用于各种各样的四组分反应。
• Microwave-assisted Knoevenagel condensation in aqueous over triazine-based microporous network
  作者：Mohd Bismillah Ansari、Mst. Nargis Parvin、Sang-Eon Park

  DOI：10.1007/s11164-013-1456-x

  日期：2014.1

  A high nitrogen-containing triazine-based microporous polymeric (TMP) network was used as an efficient metal-free catalyst for Knoevenagel condensation of ethylcyanoacetate with aromatic aldehydes. The reactions were performed in water as an environmentally benign medium, under microwave irradiation within a short reaction time of 10 min. The conversions of substituted aromatic aldehydes and selectivities for Knoevenagel products were found to be in the ranges of 44–99 and 65–99 %, respectively. The electron-withdrawing substituent showed higher conversion and selectivity as compared to electron-donating substituents. The TMP network can be readily recovered and reused up to three runs without loss in catalytic activity and selectivity.

  一种高含氮三嗪基微孔聚合物（TMP）网络被用作芳香醛与氰乙酸乙酯克诺文纳格尔缩合反应的高效无金属催化剂。反应以水为环境友好介质，在微波辐照下进行，反应时间短，仅需 10  min。研究发现，取代芳香醛的转化率和克诺文纳格尔产物的选择性分别为 44-99% 和 65-99 %。与供电子取代基相比，取电子取代基显示出更高的转化率和选择性。TMP 网络可以很容易地回收和重复使用，最多可使用三次，而不会丧失催化活性和选择性。
• Mesoporous sodalite: A novel, stable solid catalyst for base-catalyzed organic transformations
  作者：Ganapati V. Shanbhag、Minkee Choi、Jeongnam Kim、Ryong Ryoo

  DOI：10.1016/j.jcat.2009.03.014

  日期：2009.5

  Mesoporous socialite with a mesoporous/microporous hierarchical structure was successfully synthesized using an organosilane surfactant. It showed about 10-fold high surface area and 4-fold large pore volume, as compared with sodalite with solely microporous structure. The basicity of MPSOD was higher than that of CsNaX or KAIMCM-41. The catalytic activities of this mesoporous zeolite were evaluated for various base catalyzed reactions involving bulky and small substrates, viz. Knoevenagel condensation, Claisen-Schmidt condensation in liquid phase, and acetonylacetone cyclization in vapor phase. The catalyst showed higher activity and longer lifetime than CsNaX and KAIMCM-41. (C) 2009 Elsevier Inc. All rights reserved.
• Sharanin, Yu. A.; Baskakov, Yu. A.; Abramenko, Yu. T., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1870 - 1879
  作者：Sharanin, Yu. A.、Baskakov, Yu. A.、Abramenko, Yu. T.、Putsykin, Yu. G.、Vasil'ev, A. F.、Nazarova, E.B.

  DOI：——

  日期：——