N-carbamoylcinnamamide | 5962-06-1

• 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: N-carbamoylcinnamamide
• 英文别名: N-Cinnamoyl-harnstoff；Cinnamoylharnstoff；N-carbamoyl-3-phenylprop-2-enamide
• CAS: 5962-06-1
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: JDVRHVFQVXJPIH-UHFFFAOYSA-N

物化性质

• 熔点：
  207-209 °C(Solv: ethanol (64-17-5))
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-carbamoylcinnamamide 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 (+-)-2rF,3cF-dibromo-3catF-phenyl-propionic acid-ureide
  参考文献：
  名称：

  Kushnir,V.N. et al., Journal of general chemistry of the USSR, 1977, vol. 47, p. 1570 - 1574

  摘要：

  DOI：
• 作为产物：
  描述：

  4-phenyl-6-p-tolyl-5,6-dihydro-4H-pyran-2-carbothioic acid S-methyl ester 在 叠氮基三甲基硅烷 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以89%的产率得到N-carbamoylcinnamamide
  参考文献：
  名称：

  铜（II）通过C–C和C–S键断裂催化α-酮基硫代酸酯与叠氮化物的反应：N-酰基脲和酰胺的合成

  摘要：

  Cu（II）催化α-酮硫代酸酯与三甲基硅烷基叠氮化物（TMSN 3）的反应是通过C-C和C-S键断裂将硫代酯基团转化为尿素，从而构成了一种实用而直接的N合成方法-酰基脲。当在水性环境中使用二苯基磷酰基叠氮化物（DPPA）作为叠氮化物来源时，伯酰胺是通过硫代酯基团的取代而形成的。建议反应通过最初形成的α-酮酰基叠氮化物的库尔修斯重排进行以产生酰基异氰酸酯中间体，其与额外量的叠氮化物或水进一步反应并重排以提供相应的产物。为了证明该方法的潜力，已经进行了一步合成的显示抗惊厥活性的吡咯乙脲和异戊脲。

  DOI：

  10.1021/acs.joc.7b03054

文献信息

• Impact of a strong typhoon on the structure and dynamics of an old-growth beech (Fagus crenata) forest, southwestern Japan
  作者：Asuka Yamashita、Junji Sano、Shin-Ichi Yamamoto

  DOI：10.1007/bf02803187

  日期：2002.3

  Typhoon no. 19 of 1991 (T9119) caused multiple treefalls and created large openings in an old-growth beech (Fagus crenata) forest at Mt. Daisen, in the Daisen Forest Reserve, southwestern Japan. The area of the largest opening was about 1.7 ha (300 m by 70 m). To predict the dynamics of the beech stand after the disturbance of T9119, we investigated the damage to the stand and the density and growth rate of trees with DBH = 5-10 cm in a 1-ha plot covering a large part of the largest opening and the adjacent closed canopy.The beech did not regenerate immediately. The regeneration and growth rate of trees with DBH = 5-10 cm were related to the frequency of the typhoon attack for at least the past century. In beech forests, small gap formation is the prevailing mode of disturbance. Our results indicate that typhoons affect the structure and dynamics of this beech stand. We suggest that both small gap formation and large-scale disturbance are important for the maintenance of beech forest in some areas.
• Solid-Phase Synthesis of Disubstituted <i>N</i>-Acylureas from Resin-Bound Ureas and Acyl Chlorides
  作者：Hans-Georg Häcker、Manuela Meusel、Melanie Aschfalk、Michael Gütschow

  DOI：10.1021/co100020b

  日期：2011.1.10

  Acylureas (ureides) are valued for their important biological activities. Whereas cyclic acylureas have frequently been the object of solid-phase chemistry, only few reports have focused on the solid-supported preparation of acyclic representatives. We have prepared different types of acylureas on Rink amide resin in three or four steps. The products are either N-acylated (9, 18), N-acylated-N'-allcylated (10, 19), or N-acylated-N-alkylated (22). Characteristic NMR parameters of isomeric acylureas 10, 19, and 22 are discussed.
• Vuano; Pieroni; Cabaleiro, Journal of Chemical Research - Part S, 2000, # 7, p. 318 - 320
  作者：Vuano、Pieroni、Cabaleiro

  DOI：——

  日期：——
• Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C–C and C–S Bond Cleavages: Synthesis of <i>N</i>-Acylureas and Amides
  作者：Rajib Maity、Sandip Naskar、Indrajit Das

  DOI：10.1021/acs.joc.7b03054

  日期：2018.2.16

  Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C–C and C–S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of

  Cu（II）催化α-酮硫代酸酯与三甲基硅烷基叠氮化物（TMSN 3）的反应是通过C-C和C-S键断裂将硫代酯基团转化为尿素，从而构成了一种实用而直接的N合成方法-酰基脲。当在水性环境中使用二苯基磷酰基叠氮化物（DPPA）作为叠氮化物来源时，伯酰胺是通过硫代酯基团的取代而形成的。建议反应通过最初形成的α-酮酰基叠氮化物的库尔修斯重排进行以产生酰基异氰酸酯中间体，其与额外量的叠氮化物或水进一步反应并重排以提供相应的产物。为了证明该方法的潜力，已经进行了一步合成的显示抗惊厥活性的吡咯乙脲和异戊脲。
• Kushnir,V.N. et al., Journal of general chemistry of the USSR, 1977, vol. 47, p. 1570 - 1574
  作者：Kushnir,V.N. et al.

  DOI：——

  日期：——