(E)-2-benzoyl-3-(4-methoxyphenyl)acrylonitrile | 20413-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-benzoyl-3-(4-methoxyphenyl)acrylonitrile
• 英文别名: 2-benzoyl-3-(p-methoxyphenyl)-acrylonitrile；(E)-2-benzoyl-3-(4-methoxyphenyl)prop-2-enenitrile
• CAS: 20413-06-3；88137-32-0；88137-31-9
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: WISBDQKRXNGNJX-RVDMUPIBSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  445.4±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-2-benzoyl-3-(4-methoxyphenyl)acrylonitrile 在 哌啶 、 硫酸 、 sodium nitrite 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 3,5-Dicyano-4-(p-methoxyphenyl)-6-phenyl-pyrid-2-one
  参考文献：
  名称：

  Seoane, C.; Soto, J. L.; Zamorano, M. P., Heterocycles, 1980, vol. 14, # 5, p. 639 - 642

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-2-benzoyl-3-(4-methoxyphenyl)prop-2-enenitrile 生成 (E)-2-benzoyl-3-(4-methoxyphenyl)acrylonitrile
  参考文献：
  名称：

  NARUTO, SHUNSUKE;MIZUTA, HIROYUKI;YOSHIDA, TOYOKICHI;UNO, HITOSHI;KAWASHI+, CHEM. AND PHARM. BULL., 1983, 31, N 6, 2023-2032

  摘要：

  DOI：

文献信息

• Microwave synthesis of α-cyano chalcones
  作者：Shyam J. Deshpande、Paul R. Leger、Stephen R. Sieck

  DOI：10.1016/j.tetlet.2012.01.109

  日期：2012.4

  aromatic aldehydes, substituted chalcones are generated via a 15-min, one-pot synthesis. Diversification of aromatic groups, including electron-withdrawing, electron-donating, and heterocyclic substitutions, has led to the isolation of over twenty colored, solid chalcone products. Furthermore the methodology can be extended to the synthesis of benzylidenemalononitriles as well as methyl and ethyl α-cyano

  描述了一种在微波辐射下轻松生产α-氰基查耳酮的新颖方法。利用苯甲酰基乙腈和芳族醛之间的Knoevenagel缩合，通过15分钟的一锅法合成生成取代的查耳酮。芳香族基团的多样化，包括吸电子，供电子和杂环取代，已导致分离出二十多种有色固体查耳酮产品。此外，该方法可以扩展到亚苄基丙二腈以及甲基和乙基α-氰基肉桂酸酯的合成。
• Synthesis and spasmolytic activity of 2-substituted-3-(.OMEGA.-dialkylaminoalkoxyphenyl)acrylonitriles and related compounds.
  作者：SHUNSUKE NARUTO、HIROYUKI MIZUTA、TOYOKICHI YOSHIDA、HITOSHI UNO、KATSUYOSHI KAWASHIMA、TOSHIAKI KADOKAWA、HARUKI NISHIMURA

  DOI：10.1248/cpb.31.2023

  日期：——

  Several analogs of (Z)-2-(1, 2-benzisoxazol-3-yl)-3-[2-(2-piperidinoethoxy) phenyl]-acrylonitrile (1a), such as (Z)-2-(1, 2-benzisothiazol-3-yl)-, (Z)-2-(1H-indol-3-yl)-, (E)-2-(2-thienyl)-and (E)-2-benzoyl-3-(ω-dialkylaminoalkoxyphenyl) acrylonitriles (2-5), were synthesized by means of the Knoevenagel condensation. The descyano analog (6) was prepared by means of the Wittig reaction. Triethylammonium formate reduction of 1 afforded the dihydro analog (7). The spasmolytic activities of these analogs were examined. Among these compounds, (Z)-2-(1, 2-benzisothiazol-3-yl)-3-[2-(2-piperidinoethoxy) phenyl]-acrylonitrile (2a) and (Z)-2-(1, 2-benzisothiazol-3-yl)-3-[2-(2-morpholinoethoxy) phenyl]-acrylonitrile (2b) showed potent antispasmodic activities in vitro and in vivo (in mice).

  合成了几种(Z)-2-(1,2-苯异噻唑-3-基)-3-[2-(2-哌嗪乙氧基)苯基]-丙烯腈(1a)的类似物，如(Z)-2-(1,2-苯异噻唑-3-基)-、(Z)-2-(1H-吲哚-3-基)-、(E)-2-(2-噻吩基)-和(E)-2-苯甲酰基-3-(ω-二烷基氨基醇苯基)丙烯腈(2-5)，这些化合物是通过Knoevenagel缩合法合成的。去氰类似物(6)是通过Wittig反应制备的。将1与三乙基氨基甲酸盐还原得到二氢类似物(7)。对这些类似物的镇痉活性进行了研究。在这些化合物中，(Z)-2-(1,2-苯异噻唑-3-基)-3-[2-(2-哌嗪乙氧基)苯基]-丙烯腈(2a)和(Z)-2-(1,2-苯异噻唑-3-基)-3-[2-(2-吗啉乙氧基)苯基]-丙烯腈(2b)在体外和体内（小鼠）均表现出强效的抗痉挛活性。
• Asymmetric Inverse-Electron-Demand Oxa-Diels–Alder Reaction of Allylic Ketones through Dienamine Catalysis
  作者：Ming-Lin Shi、Gu Zhan、Su-Lan Zhou、Wei Du、Ying-Chun Chen

  DOI：10.1021/acs.orglett.6b03384

  日期：2016.12.16

  A remote β,γ-regioselective asymmetric inverse-electron-demand oxa-Diels–Alder reaction between allylic ketones and α-cyano-α,β-unsaturated ketones has been developed through induced extended dienamine catalysis of a cinchona-derived primary amine. A spectrum of densely substituted dihydropyran frameworks were efficiently produced with excellent enantioselectivity and fair to exclusive diastereoselectivity

  通过诱导金鸡纳酮衍生的伯胺的扩展二烯胺催化作用，已开发出烯丙基酮与α-氰基-α，β-不饱和酮之间的远程β，γ-区域选择性不对称逆电子要求的oxa-Diels-Alder反应。高效地生产了一系列稠密取代的二氢吡喃骨架，具有出色的对映选择性和对等非对映选择性。
• Reduced graphene oxide supported piperazine in aminocatalysis
  作者：Eduardo Rodrigo、Beatriz García Alcubilla、Raquel Sainz、J. L. García Fierro、Rafael Ferritto、M. Belén Cid

  DOI：10.1039/c4cc02701a

  日期：——

  Reduced graphene oxide (rGO) has been used as a support for piperazine to provide a heterogeneous bifunctional organocatalyst (rGO-NH) that is able to efficiently promote vintage organic transformations such as Knoevenagel, Michael and aldol reactions. The obtained results suggest a significant role of the support in the course of these reactions.

  还原氧化石墨烯（rGO）被用作哌嗪的载体，以提供一种能够高效促进老式有机转化反应的异相双功能有机催化剂（rGO-NH），例如Knoevenagel反应、迈克尔反应和醛醇反应。获得的结果表明，载体在这些反应过程中发挥了重要作用。
• New routes to the synthesis of pyridazinone, ethoxypyridine, pyrazole and pyrazolo[1,5-<i>a</i>]pyrimidine derivatives incorporating a benzotriazole moiety
  作者：Fatima Al-Omran、Osama Yousef Abd El-Hay、Adel Abou El-Khair

  DOI：10.1002/jhet.5570370635

  日期：2000.11

  A new approach to the synthesis of pyridazinone, ethoxypyridine, pyrazole and 7-aminopyrazolo-[1,5-a]pyrimidine derivatives. The structure of the newly synthesized compounds was elucidated by elemental analyses, ir, 1H nmr spectra and in some cases by 13C nmr investigations.

  合成哒嗪酮，乙氧基吡啶，吡唑和7-氨基吡唑并-[1,5- a ]嘧啶衍生物的新方法。通过元素分析，ir，1 H nmr光谱以及在某些情况下通过13 C nmr研究阐明了新合成化合物的结构。

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