2-丙烯酸,2,3,3-三氰基-,甲基酯 | 101342-43-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-丙烯酸,2,3,3-三氰基-,甲基酯
• 英文名称: methyl tricyanoethylenecarboxylate
• 英文别名: 2,3,3-Tricyano-acrylic acid methyl ester；methyl 2,3,3-tricyanoprop-2-enoate
• CAS: 101342-43-2
• 化学式: C₇H₃N₃O₂
• 分子量: 161.12
• InChiKey: YXKNBAVLYLPADR-UHFFFAOYSA-N

物化性质

• 熔点：
  89.5-90.5 °C
• 沸点：
  276.6±40.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  97.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(pentamethylcyclopentadienyl)chromium 、 2-丙烯酸,2,3,3-三氰基-,甲基酯 以 二氯甲烷 为溶剂， 以61%的产率得到decamethylchromocenium methyl tricyanoethylenecarboxylate
  参考文献：
  名称：

  使用三氰基亚乙基羧酸甲酯 (MTCE) 作为电子受体的十甲基茂金属电荷转移盐磁铁家族

  摘要：

  三氰基乙烯羧酸甲酯 (MTCE) 已被用作单电子受体构件，用于合成式 [MCp*2][MTCE]、M = Cr、Mn 和 Fe 的同晶十甲基茂金属电荷转移盐磁体。在功能和电化学方面，MTCE 是四氰基乙烯 (TCNE) 和二氰基富马酸二甲酯 (DMeDCF) 的混合物，这两种受体以前已被发现支持铁磁性。铬类似物的 X 射线晶体结构 [CrCp*2][MTCE] 表明它存在于正交空间群 Pnma 中预期的混合堆叠结构中，a = 14.739(3) A, b = 10.7869(19 ) A 和 c = 15.771(3) A 和 Z = 4。正如预期的那样，所有三个家族成员都表现出占主导地位的铁磁耦合，据推测这反映了叠内相互作用。然而，体磁特性主要不同于对其 TCNE 和 DMeDCF 类似物特性的简单内插或外推。密度泛函理论计算已被用于阐明这一观察结果。

  DOI：

  10.1021/ja0457213
• 作为产物：
  描述：

  methyl 2,3,3-tricyano-7-(propan-2-ylidene)bicyclo[2.2.1]hept-5-ene-2-carboxylate 以 氘代氯仿 为溶剂， 生成 6,6-二甲基-5-亚甲基-1,3-环戊二烯 、 2-丙烯酸,2,3,3-三氰基-,甲基酯
  参考文献：
  名称：

  Reversible Diels−Alder Reactions for the Generation of Dynamic Combinatorial Libraries

  摘要：

  Condensation reactions between various dienes and dienophiles have been screened for reversibility. Functionalized fulvenes, bearing in particular biological groups, and cyanolefins have been found to react rapidly and reversibly, in the temperature range from -10 to +50 degreesC. These results pave the way for the development of dynamic combinatorial libraries based on reversible Diels-Alder chemistry.

  DOI：

  10.1021/ol048065k

文献信息

• Room Temperature Dynamic Polymers Based on Diels-Alder Chemistry
  作者：P. Reutenauer、E. Buhler、P. J. Boul、S. J. Candau、J.-M. Lehn

  DOI：10.1002/chem.200802145

  日期：2009.2.9

  Polymer, heal thyself! Dynamic polymers formed by a reversible Diels–Alder reaction were formed and studied by using neutron scattering at room temperature. They were used to obtain thin films that displayed self‐healing at room temperature (see figure).

  聚合物，治愈自己！由可逆的狄尔斯-阿尔德反应形成的动态聚合物是通过在室温下使用中子散射来形成和研究的。它们被用来获得在室温下表现出自愈性的薄膜（见图）。
• Cycloaddition and copolymerization of methyl tricyanoethylenecarboxylate with electron-rich olefins
  作者：H. K. Hall、Anne Buyle Padias、Tun Fun Way、Bridgette Bergami

  DOI：10.1021/jo00234a006

  日期：1987.12
• Zwitterionic tetramethylenes as the common intermediates in the cycloaddition and polymerization reactions of N-vinylcarbazole with electrophilic tetrasubstituted ethylenes: a new explanation for charge-transfer initiation
  作者：Tetsuya. Gotoh、Anne Buyle. Padias、H. K. Hall

  DOI：10.1021/ja00276a037

  日期：1986.8
• HALL, H. K., JR.;PADIAS, ANNE BUYLE;WAY, TUN-FUN;BERGAMI, BRIDGETTE, J. ORG. CHEM., 52,(1987) N 25, 5528-5531
  作者：HALL, H. K., JR.、PADIAS, ANNE BUYLE、WAY, TUN-FUN、BERGAMI, BRIDGETTE

  DOI：——

  日期：——
• NOVEL ADDUCT COMPOUND, METHODS FOR PURIFICATION AND PREPARATION OF FUSED POLYCYCLIC AROMATIC COMPOUND, SOLUTION FOR FORMATION OF ORGANIC SEMICONDUCTOR FILM, AND NOVEL ALPHA-DIKETONE COMPOUND
  申请人：Ikeda Yoshinori

  公开号：US20120211731A1

  公开（公告）日：2012-08-23

  Provided are a novel adduct compound and a novel α-diketone compound, from which organic semiconductor layers consisting of a fused polycyclic aromatic compound can be formed by a solution method, said solution method being generally easier than a deposition method. Also provided are a method for the purification of the adduct compound, and a solution for the formation of organic semiconductor film, which contains the adduct compound. The adduct compound has a structure wherein a compound having a double bond is added in an eliminable state to a fused polycyclic aromatic compound of general formula (I): Ar 1 Ar 2 Ar 3 (I), while the α-diketone compound has a structure wherein a compound having a double bond is added in an eliminable state to a fused polycyclic aromatic compound. The fused polycyclic aromatic compound is dinaphthothienothiophene or the like, while the compound having a double bond is hexachlorocyclopentadiene or the like. In general formula (I), Ar 1 , Ar 2 and Ar 3 are each as defined in the description.