cinnamyl phenylcarbamate | 25076-44-2

• 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: cinnamyl phenylcarbamate
• 英文别名: 3-phenylprop-2-enyl N-phenylcarbamate
• CAS: 25076-44-2
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: DXODDGVNDLOMLO-UHFFFAOYSA-N

物化性质

• 沸点：
  375.8±31.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 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：

  cinnamyl phenylcarbamate 在 Ir(dF(CF₃)ppy)₂(bpy)PF₆ 、 苯硫酚 、 tetrabutylammonium dibutyl phosphate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以81%的产率得到4-benzyl-3-phenyloxazolidin-2-one
  参考文献：
  名称：

  Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer

  摘要：

  Here we report a ternary catalyst system for the intramolecular hydroamidation of unactivated olefins using simple N-aryl amide derivatives. Amide activation in these reactions occurs via concerted proton-coupled electron transfer (PCET) mediated by an excited state iridium complex and weak phosphate base to furnish a reactive amidyl radical that readily adds to pendant alkenes. A series of H-atom, electron, and proton transfer events with a thiophenol cocatalyst furnish the product and regenerate the active forms of the photocatalyst and base. Mechanistic studies indicate that the amide substrate can be selectively homolyzed via PCET in the presence of the thiophenol, despite a large difference in bond dissociation free energies between these functional groups.

  DOI：

  10.1021/jacs.5b09671
• 作为产物：
  描述：

  肉桂醇 、 异氰酸苯酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到cinnamyl phenylcarbamate
  参考文献：
  名称：

  烯烃分子内脱氢胺化通过双有机光氧化还原和钴催化在没有氢受体的情况下进行

  摘要：

  在没有牺牲氢受体的情况下，直接 C-H/N-H 脱氢偶联是一种有前途但在热力学上不利的转变。在此，通过协同光氧化还原和钴催化与H 2释放，实现了概念上新颖的烯烃无氧化剂脱氢胺化。通过这种方法，合成了具有优异原子经济性的多种五元 N-杂环。绿色系统将解决对传统氧化条件敏感的挑战。此外，讨论了该方法的范围和机械细节。

  DOI：

  10.1039/d2gc02084j

文献信息

• Palladium-Catalyzed Allylidenation of Aldehyde. A Simple and Convenient Method for the Preparation of Conjugated Diene and Polyene Compounds
  作者：Nobuhisa Okukado、Osamu Uchikawa、Yukari Nakamura

  DOI：10.1246/cl.1988.1449

  日期：1988.8.5

  situ reacted with aldehydes to give conjugated dienes in good yields in the presence of tributylphosphine and a catalytic amount of Pd(PPh3)4. This method proved to be suitable for the preparation of polyene compounds such as carotenoids.

  在三丁基膦和催化量的 Pd(PPh3)4 存在下，由烯丙醇和异氰酸苯酯原位制备的烯丙基苯基氨基甲酸酯与醛反应以良好的产率得到共轭二烯。该方法被证明适用于制备多烯化合物，如类胡萝卜素。
• Preparation of<i>N</i>-Substituted Aryl and Alkyl Carbamates and Their Inhibitory Effect on Oat Seed Germination
  作者：Babak Heidary ALIZADEH、Takeyoshi SUGIYAMA、Takayuki ORITANI、Shigefumi KUWAHARA

  DOI：10.1271/bbb.66.422

  日期：2002.1

  A series of N-substituted aryl and alkyl carbamates (RNHCOOR'; R: aryl, alkyl; R': aryl, alkyl) was prepared and screened for inhibitory activity toward the germination of oat seeds. The activity of each compound was compared with that of chlorpropham (isopropyl 3-chlorocarbanilate). Some of the synthetic carbamates possessing the N-(phenylthio)methyl group, PhSCH2NHCOOR', showed inhibitory activity

  制备了一系列的N-取代的芳基和氨基甲酸烷基酯（RNHCOOR'； R：芳基，烷基； R'：芳基，烷基），并筛选了对燕麦种子发芽的抑制活性。将每种化合物的活性与氯丙胺（3-氯氨基甲酸异丙酯）的活性进行比较。一些具有N-（苯硫基）甲基的合成氨基甲酸酯PhSCH2NHCOOR'表现出与氯丙胺接近或相当的抑制活性。
• Aminoacylation of Alkenes by Cooperative NHC and Photoredox Catalysis
  作者：Lena Lezius、Jannik Reimler、Armido Studer、Nadine Döben、Michael Hamm、Constantin G. Daniliuc

  DOI：10.1055/a-2145-8697

  日期：2024.3

  the combination of these two catalytic modes. The key step is a radical/radical cross-coupling between a persistent ketyl radical and a transient benzylic or aliphatic C-radical, which is generated through radical cyclization of an oxidatively formed amidyl radical. Several carbamates, amides and sulfonamides containing an alkene moiety and different acyl fluorides can be used as substrates. The resulting

  近年来，NHC 和光氧化还原协同催化作为一个新兴的研究领域受到了广泛的关注。在此，我们报告了烯烃的环化氨酰化，这是通过这两种催化模式的组合实现的。关键步骤是持久的羰基和瞬时的苄基或脂肪族C-自由基之间的自由基/自由基交叉偶联，这是通过氧化形成的酰胺自由基的自由基环化产生的。含有烯烃部分和不同酰基氟化物的几种氨基甲酸酯、酰胺和磺酰胺可用作底物。所得产品的收率中等至良好。
• DE1916971
  申请人：——

  公开号：——

  公开（公告）日：——
• Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer
  作者：David C. Miller、Gilbert J. Choi、Hudson S. Orbe、Robert R. Knowles

  DOI：10.1021/jacs.5b09671

  日期：2015.10.28

  Here we report a ternary catalyst system for the intramolecular hydroamidation of unactivated olefins using simple N-aryl amide derivatives. Amide activation in these reactions occurs via concerted proton-coupled electron transfer (PCET) mediated by an excited state iridium complex and weak phosphate base to furnish a reactive amidyl radical that readily adds to pendant alkenes. A series of H-atom, electron, and proton transfer events with a thiophenol cocatalyst furnish the product and regenerate the active forms of the photocatalyst and base. Mechanistic studies indicate that the amide substrate can be selectively homolyzed via PCET in the presence of the thiophenol, despite a large difference in bond dissociation free energies between these functional groups.