(E)-5-Phenyl-3-pentenamide | 124033-83-6

• 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: (E)-5-Phenyl-3-pentenamide
• 英文别名: (E)-5-phenylpent-3-enamide
• CAS: 124033-83-6
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: GDDGLEJMOYJZSL-SNAWJCMRSA-N

物化性质

• 沸点：
  366.4±31.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-乙烯氮杂啶-2-酮 、 氯化苯汞 在 氯化铵 、 lithium chloride 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-5-Phenyl-3-pentenamide 、 (E)-5-Phenyl-3-pentenamide
  参考文献：
  名称：

  Palladium(II)-promoted cross-coupling of 4-alkenyl-2-azetidinones with organomercurials

  摘要：

  The palladium-promoted cross-coupling of 4-alkenyl-2-azetidinones with aryl and vinylic mercurials provides 5-aryl-3-alkenamides and 3,6-alkadienamides, respectively. Modest to excellent stereoselectivity for formation of the new carbon-carbon double bond is observed. The reaction becomes catalytic in palladium when cupric chloride and oxygen are introduced. This process constitutes the first organometallic ring opening of 2-azetidinones to acyclic unsaturated amides.

  DOI：

  10.1021/jo00060a024

文献信息

• Fused quinoline derivative and use thereof
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2080760A1

  公开（公告）日：2009-07-22

  Use of a compound represented by the formula (I) wherein R1 is (1) unsubstituted, (2) a hydrogen atom, (3) a hydrocarbon group optionally having substituent(s) or (4) acyl; R2 is (1) a hydrogen atom, (2) a hydrocarbon group optionally having substituent(s), (3) hydroxy optionally having a substituent, (4) amino optionally having substituent(s), (5) thiol optionally having a substituent, (6) a heterocyclic group optionally having substituent(s) or (7) acyl; R3 is (1) unsubstituted, (2) a hydrogen atom, (3) a hydrocarbon group optionally having substituent(s), (4) hydroxy optionally having a substituent, (5) amino optionally havingsubstituent(s), (6) thiol optionally having a substituent or (7) acyl; R4 and R5 are the same or different and each is (1) a hydrogen atom, (2) a hydrocarbon group optionally having substituent (s), (3) hydroxyoptionallyhavingasubstituent, (4) amino optionally having substituent (s), (5) thiol optionally having a substituent or (6) acyl; R6 is (1) (cyclic group optionally having substituent(s))-carbonyl, (2) alkenylcarbonyl optionally having substituent (s), (3) alkylcarbonyl having substituent (s) selected from (i) cycloalkyl optionally having substituent (s), (ii) amino optionally having substituent(s) and (iii) a heterocyclic group optionally having substituent(s) or (4) a heterocyclic group optionally having substituent(s); R7, R8, R9 and R10 are the same or different and each is (1) a hydrogen atom, (2) halogen, (3) cyano, (4) nitro, (5) a hydrocarbon group optionally having substituent(s), (6) hydroxy optionally having a substituent, (7) amino optionally having substituent(s), (8) thiol optionally having a substituent, (9) a heterocyclic group optionally having substituent(s) or (10) acyl; or R7 and R8, R8 and R9, and R9 and R10 may form a ring together with the adjacent carbon atoms; n is an integer of 1 to 5; --- represents unsubstituted or a single bond; and; --- represents a single bond or a double bond, or a salt thereof, for the production of an agent for the prophylaxis or treatment of melancholia.

  使用式 (I) 所代表的化合物 其中 R1 是(1)未取代的氢原子，(2)氢原子，(3)任选具有取代基的烃基或(4)酰基； R2 是(1)氢原子，(2)任选具有取代基的烃基，(3)任选具有取代基的羟基，(4)任选具有取代基的氨基，(5)任选具有取代基的硫醇，(6)任选具有取代基的杂环基团或(7)酰基； R3 是(1)未取代的，(2)氢原子，(3)任选具有取代基的烃基，(4)任选具有取代基的羟基，(5)任选具有取代基的氨基，(6)任选具有取代基的硫醇或(7)酰基； R4 和 R5 相同或不同，各自是 (1) 氢原子，(2) 可选择具有取代基的烃基，(3) 可选择具有取代基的羟基，(4) 可选择具有取代基的氨基，(5) 可选择具有取代基的硫醇或 (6) 丙烯酸； R6 是(1)（任选具有取代基的环基）-羰基，(2)任选具有取代基的烯基羰基，(3)任选具有取代基的烷基羰基，这些取代基选自(i)任选具有取代基的环烷基，(ii)任选具有取代基的氨基和(iii)任选具有取代基的杂环基团或(4)任选具有取代基的杂环基团； R7、R8、R9 和 R10 相同或不同，且各自为：(1) 氢原子，(2) 卤素，(3) 氰基，(4) 硝基，(5) 任选具有取代基的烃基，(6) 任选具有取代基的羟基，(7) 任选具有取代基的氨基，(8) 任选具有取代基的硫醇，(9) 任选具有取代基的杂环基团或 (10) 丙烯酸基；或 R7 和 R8、R8 和 R9 以及 R9 和 R10 可与相邻的碳原子一起形成一个环； n 是 1 至 5 的整数； ----代表未取代或单键；以及 ----代表单键或双键，或其盐，用于生产预防或治疗忧郁症的制剂。
• Cooperative Fe/Co-Catalyzed Remote Desaturation for the Synthesis of Unsaturated Amide Derivatives
  作者：Yanjun Wan、Emmanuel Ramírez、Ayzia Ford、Harriet K. Zhang、Jack R. Norton、Gang Li

  DOI：10.1021/jacs.3c14481

  日期：2024.2.21

  Unsaturated amides represent common functional groups found in natural products and bioactive molecules and serve as versatile synthetic building blocks. Here, we report an iron(II)/cobalt(II) dual catalytic system for the syntheses of distally unsaturated amide derivatives. The transformation proceeds through an iron nitrenoid-mediated 1,5-hydrogen atom transfer (1,5-HAT) mechanism. Subsequently,

  不饱和酰胺代表天然产物和生物活性分子中常见的官能团，可作为多功能合成构件。在这里，我们报道了一种用于合成远端不饱和酰胺衍生物的铁（II）/钴（II）双催化系统。该转化通过铁氮烯介导的 1,5-氢原子转移 (1,5-HAT) 机制进行。随后，自由基中间体在钴肟催化剂的作用下从邻位亚甲基中夺取氢原子，在温和的条件下有效地生成β,γ-或γ,δ-不饱和酰胺衍生物。共介 HAT 的效率可以通过改变不同的辅助设备来调整，突出了该协议的通用性。值得注意的是，这种去饱和方案还适合实际的可扩展性，能够合成不饱和氨基甲酸酯和脲，它们可以很容易地转化为各种有价值的分子。
• Synthesis of aryl-substituted 3-alkenamides via palladium-catalyzed cross-coupling of aryl iodides and 4-alkenyl-2-azetidinones
  作者：Richard C. Larock、Shuji Ding

  DOI：10.1016/s0040-4039(00)77470-3

  日期：1993.2

  Palladium catalyzes the cross-coupling of aryl iodides and 4-alkenyl-2-azetidinones to give good yields of aryl-substituted 3-alkenamides.
• LAROCK, RICHARD C.;DING, SHUJI, TETRAHEDRON LETT., 30,(1989) N5, C. 1897-1900
  作者：LAROCK, RICHARD C.、DING, SHUJI

  DOI：——

  日期：——
• Palladium(II)-promoted cross-coupling of 4-alkenyl-2-azetidinones with organomercurials
  作者：Richard C. Larock、Shuji Ding

  DOI：10.1021/jo00060a024

  日期：1993.4

  The palladium-promoted cross-coupling of 4-alkenyl-2-azetidinones with aryl and vinylic mercurials provides 5-aryl-3-alkenamides and 3,6-alkadienamides, respectively. Modest to excellent stereoselectivity for formation of the new carbon-carbon double bond is observed. The reaction becomes catalytic in palladium when cupric chloride and oxygen are introduced. This process constitutes the first organometallic ring opening of 2-azetidinones to acyclic unsaturated amides.