4-(cyanomethyl)-N,N-dimethylbenzamide | 120352-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(cyanomethyl)-N,N-dimethylbenzamide
• CAS: 120352-92-3
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: YSKRZISUFYPAMN-UHFFFAOYSA-N

物化性质

• 沸点：
  374.5±25.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(cyanomethyl)-N,N-dimethylbenzamide 在 sodium tetrahydroborate 、 sodium amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 4-[3-cyano-6-[3-(3-methoxyphenoxy)propyl-methylamino]-2-methylhexan-3-yl]-N,N-dimethylbenzamide
  参考文献：
  名称：

  Novel phenoxyalkylamine derivatives. IV. Synthesis, Ca2+-antagonistic activity and quantitative structure-activity analysis of .ALPHA.-isopropyl-.ALPHA.-(3-(3-(3-methoxyphenoxy)propylamino)propyl)-.ALPHA.-phenylacetonitrile derivatives.

  摘要：

  制备了α-异丙基-α-[3-[3-(3-甲氧基苯氧基)丙氨基]丙基]-α-苯乙腈衍生物，并评估了它们的 Ca2+ 拮抗活性。在这些化合物中，发现在 A 环上具有 m-OMe、p-F、p-Cl、3，4-(OMe) 2 和 3，5-(OMe) 2 取代基的 N-Me 衍生物比维拉帕米具有更高的 Ca2+ 拮抗活性。利用物理化学取代基参数和回归分析对 A 环上取代基的影响进行了定量研究。分析结果表明，π值接近于零的取代基对活性有利，而 m 和 p 取代基存在最佳立体条件，相当于 m-OMe 和 p-F 或 p-Cl。对同时改变 A 环、苯氧基苯环（B 环）和季碳原子上的取代基的全系列类似物进行的分析表明，除了特定位置的立体效应和疏水效应外，还存在最佳的分子疏水性，这可能参与了向作用部位的迁移过程。

  DOI：

  10.1248/cpb.36.4103
• 作为产物：
  描述：

  4-(氰甲基)苯甲酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 30.0h， 生成 4-(cyanomethyl)-N,N-dimethylbenzamide
  参考文献：
  名称：

  From donor and acceptor substitutedmeta- andpara-xylenes topara-Quinodimethanes and Poly(meta-phenylenevinylene)s

  摘要：

  Ortho-, meta-and para-xylenes 1, 13a, 13b and 13c, with donor and acceptor substituents at the alpha- and alpha' positions, lead to a remarkable variety of intermediates and reaction products after deprotonation of the benzylic proton. Thus, the reaction of para-(cyanomethyl)dialkyl[(methylthio)phenylmethylene] ammonium tetrafluoroborates 13a and 13b with sodium hydride affords the para-quinodimethanes 14a and 14b. Poly(meta-phenylenevinylene) 14c can be obtained when starting from 13c. We report the synthesis of para-quinodimethanes 14a and 14b and poly(metaphenylenevinylene) 14c and describe a successive approach towards meta-phenylenevinylenes of definite length 16b and 17b starting from 12d. Moreover, we compare the stability and reactivity of para-quinodimethane 14a and 14b with those of the ortho-quinodimethane 2 and we focus on the characterization of the resulting donor and acceptor substituted compounds.

  DOI：

  10.1002/prac.19983400412

文献信息

• Computer‐Driven Development of Ylide Functionalized Phosphines for Palladium‐Catalyzed Hiyama Couplings
  作者：Jonas F. Goebel、Julian Löffler、Zhongyi Zeng、Jens Handelmann、Albert Hermann、Ilja Rodstein、Tobias Gensch、Viktoria H. Gessner、Lukas J. Gooßen

  DOI：10.1002/anie.202216160

  日期：2023.2.20

  Ylide functionalized phosphines were tailored supported by computational inverse catalyst design to fit the requirements of mild Hiyama couplings of aryl chlorides. YPhos/Pd catalyst is highly efficient for the coupling with aryl chlorides in general, and the reaction shows excellent functional group compatibility.

  Ylide 官能化膦是在计算逆催化剂设计的支持下定制的，以满足芳基氯的温和 Hiyama 偶联的要求。通常，YPhos/Pd 催化剂与芳基氯的偶联效率很​​高，并且反应显示出优异的官能团相容性。
• MITANI, KAZUYA;SAKURAI, SHUNICHIRO;SUZUKI, TOSHIHIRO;NORIKAWA, KOJI;KOSHI+, CHEM. AND PHARM. BULL., 36,(1988) N0, C. 4101-4120
  作者：MITANI, KAZUYA、SAKURAI, SHUNICHIRO、SUZUKI, TOSHIHIRO、NORIKAWA, KOJI、KOSHI+

  DOI：——

  日期：——
• Novel phenoxyalkylamine derivatives. IV. Synthesis, Ca2+-antagonistic activity and quantitative structure-activity analysis of .ALPHA.-isopropyl-.ALPHA.-(3-(3-(3-methoxyphenoxy)propylamino)propyl)-.ALPHA.-phenylacetonitrile derivatives.
  作者：KAZUYA MITANI、SHUNICHIRO SAKURAI、TOSHIHIRO SUZUKI、KOJI MORIKAWA、EIICHI KOSHINAKA、HIDEO KATO、YASUO ITO、TOSHIO FUJITA

  DOI：10.1248/cpb.36.4103

  日期：——

  α-Isopropyl-α-[3-[3-(3-methoxyphenoxy) propylamino] propyl] -α-phenylacetonitrile derivatives containing various substituents on the benzene ring (A ring) at the phenylacetonitrile moiety were prepared, and their Ca2+-antagonistic activity was evaluated. Among these compounds, the N-Me derivatives with m-OMe, p-F, p-Cl, 3, 4-(OMe) 2 and 3, 5-(OMe) 2 substituents on the A ring were found to show higher Ca2+-antagonistic activity than verapamil. The effect of substituents on the A ring was examined quantitatively using physicochemical substituent parameters and regression analysis. The analysis showed that substituents with a π value close to zero are favorable to the activity and that optimum steric conditions exist for m-and p-substituents, corresponding to those of m-OMe and p-F or p-Cl. The analysis for the whole series of analogs where substituents on the A ring, the benzene ring (B ring) at the phenoxy moiety and the quaternary carbon atom are simultaneously varied suggested that there is an optimum molecular hydrophobicity, perhaps participating in the transport process to the site of action, besides position-specific steric and hydrophobic effects.

  制备了α-异丙基-α-[3-[3-(3-甲氧基苯氧基)丙氨基]丙基]-α-苯乙腈衍生物，并评估了它们的 Ca2+ 拮抗活性。在这些化合物中，发现在 A 环上具有 m-OMe、p-F、p-Cl、3，4-(OMe) 2 和 3，5-(OMe) 2 取代基的 N-Me 衍生物比维拉帕米具有更高的 Ca2+ 拮抗活性。利用物理化学取代基参数和回归分析对 A 环上取代基的影响进行了定量研究。分析结果表明，π值接近于零的取代基对活性有利，而 m 和 p 取代基存在最佳立体条件，相当于 m-OMe 和 p-F 或 p-Cl。对同时改变 A 环、苯氧基苯环（B 环）和季碳原子上的取代基的全系列类似物进行的分析表明，除了特定位置的立体效应和疏水效应外，还存在最佳的分子疏水性，这可能参与了向作用部位的迁移过程。
• From donor and acceptor substitutedmeta- andpara-xylenes topara-Quinodimethanes and Poly(meta-phenylenevinylene)s
  作者：Carsten Former、Gerrit Kl�rner、Manfred Wagner、Klaus M�llen

  DOI：10.1002/prac.19983400412

  日期：——

  Ortho-, meta-and para-xylenes 1, 13a, 13b and 13c, with donor and acceptor substituents at the alpha- and alpha' positions, lead to a remarkable variety of intermediates and reaction products after deprotonation of the benzylic proton. Thus, the reaction of para-(cyanomethyl)dialkyl[(methylthio)phenylmethylene] ammonium tetrafluoroborates 13a and 13b with sodium hydride affords the para-quinodimethanes 14a and 14b. Poly(meta-phenylenevinylene) 14c can be obtained when starting from 13c. We report the synthesis of para-quinodimethanes 14a and 14b and poly(metaphenylenevinylene) 14c and describe a successive approach towards meta-phenylenevinylenes of definite length 16b and 17b starting from 12d. Moreover, we compare the stability and reactivity of para-quinodimethane 14a and 14b with those of the ortho-quinodimethane 2 and we focus on the characterization of the resulting donor and acceptor substituted compounds.