(E)-N,2-dimethyl-3-phenylprop-2-enamide | 98876-16-5

• 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: (E)-N,2-dimethyl-3-phenylprop-2-enamide
• CAS: 98876-16-5；105906-93-2；131214-23-8
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: BDDNGLQSBHBGBQ-CMDGGOBGSA-N

物化性质

• 沸点：
  355.7±25.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N,2-dimethyl-3-phenylprop-2-enamide 以 二氯甲烷 为溶剂， 生成 (Z)-N,2-dimethyl-3-phenylprop-2-enamide
  参考文献：
  名称：

  Lewis-acid catalysis of photochemical reactions. 9. Structure and photoisomerization of (E)- and (Z)-cinnamamides and their Lewis acid complexes

  摘要：

  The spectroscopic properties and photoisomerization reactions of several (E)- and (Z)-cinnamamides have been investigated in the absence and presence of the strong Lewis acid BF3. The (E)-cinnamamides are essentially planar and exist predominantly in the enone s-cis conformation, except in the case of the alpha-methyl tertiary amide which adopts the s-trans conformation in order to minimize nonbonded repulsion. The (Z)-cinnamamides exist predominantly in the highly nonplanar s-trans conformation. This unusual conformational preference is attributed to intramolecular charge transfer from the aromatic to amide functionality. Photoisomerization efficiencies are dependent upon N-alkylation, aromatic substitution, alpha-alkylation, solvent, and excitation wavelength. These effects are attributed to the existence of two lowest energy pi,pi* singlet states (one reactive and one nonreactive) whose relative energies are dependent upon substitution. The cinnamamides from 1:1 complexes with BF3 with equilibrium constants > 10(3). Complexation alters both the electronic structure and photochemical behavior of the cinnamamides. Quantitative E --> Z isomerization has been observed for the BF3 complexes of two tertiary amides.

  DOI：

  10.1021/jo00002a015
• 作为产物：
  描述：

  (Z)-N,2-dimethyl-3-phenylprop-2-enamide 以 二氯甲烷 为溶剂， 生成 (E)-N,2-dimethyl-3-phenylprop-2-enamide
  参考文献：
  名称：

  Lewis-acid catalysis of photochemical reactions. 9. Structure and photoisomerization of (E)- and (Z)-cinnamamides and their Lewis acid complexes

  摘要：

  The spectroscopic properties and photoisomerization reactions of several (E)- and (Z)-cinnamamides have been investigated in the absence and presence of the strong Lewis acid BF3. The (E)-cinnamamides are essentially planar and exist predominantly in the enone s-cis conformation, except in the case of the alpha-methyl tertiary amide which adopts the s-trans conformation in order to minimize nonbonded repulsion. The (Z)-cinnamamides exist predominantly in the highly nonplanar s-trans conformation. This unusual conformational preference is attributed to intramolecular charge transfer from the aromatic to amide functionality. Photoisomerization efficiencies are dependent upon N-alkylation, aromatic substitution, alpha-alkylation, solvent, and excitation wavelength. These effects are attributed to the existence of two lowest energy pi,pi* singlet states (one reactive and one nonreactive) whose relative energies are dependent upon substitution. The cinnamamides from 1:1 complexes with BF3 with equilibrium constants > 10(3). Complexation alters both the electronic structure and photochemical behavior of the cinnamamides. Quantitative E --> Z isomerization has been observed for the BF3 complexes of two tertiary amides.

  DOI：

  10.1021/jo00002a015

文献信息

• An Efficient and General Method for the Heck and Buchwald–Hartwig Coupling Reactions of Aryl Chlorides
  作者：Dong-Hwan Lee、Abu Taher、Shahin Hossain、Myung-Jong Jin

  DOI：10.1021/ol202177k

  日期：2011.10.21

  The β-diketiminatophosphane Pd complex acted as a powerful catalyst for the Heck coupling of aryl chlorides with alkenes. Various aryl and heteroaryl chlorides were coupled efficiently under relatively mild conditions. Furthermore, this catalytic system also proved to be highly active in the Buchwald–Hartwig coupling of deactivated and sterically hindered aryl chlorides at room temperature.

  β-二酮基亚氨基膦Pd络合物可作为芳基氯化物与烯烃的Heck偶联的有力催化剂。在相对温和的条件下有效地偶联了各种芳基和杂芳基氯化物。此外，在室温下，这种催化体系在失活的和位阻的芳基氯化物的布赫瓦尔德-哈特维格偶联中也被证明具有很高的活性。
• [EN] PYRAN DERVATIVES AS CYP11A1 (CYTOCHROME P450 MONOOXYGENASE 11A1) INHIBITORS<br/>[FR] DÉRIVÉS DE PYRANE EN TANT QU'INHIBITEURS DE CYP11A1 (CYTOCHROME P450 MONOOXYGÉNASE 11A1)
  申请人：ORION CORP

  公开号：WO2018115591A1

  公开（公告）日：2018-06-28

  Compounds of formula (I) wherein R1, R2,R3,R4,R5,R23,R24,L, A and Bare as defined in claim 1, or pharmaceutically acceptable salts thereof are disclosed. The compounds of formula (I) possess utility as cytochrome P450 monooxygenase 11A1(CYP11A1) inhibitors. The compounds are useful as medicaments in the treatment of steroidreceptor, particularly androgen receptor,dependent diseases and conditions, such asprostate cancer.

  公式(I)的化合物，其中R1、R2、R3、R4、R5、R23、R24、L、A和B如权利要求1中定义，或其药用可接受的盐被披露。公式(I)的化合物具有作为细胞色素P450单加氧酶11A1（CYP11A1）抑制剂的使用价值。这些化合物作为药物用于治疗激素受体，尤其是雄激素受体相关的疾病和状况，如前列腺癌。
• [EN] INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA REPLICATION DU VIRUS DE L'IMMUNODEFICIENCE HUMAINE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010130034A1

  公开（公告）日：2010-11-18

  Compounds of formula I wherein a, R1, R2, R3, R4, R5 and R6 are defined herein, are useful as inhibitors of HIV replication.

  式I中的化合物，其中a、R1、R2、R3、R4、R5和R6如本文所定义，可用作HIV复制抑制剂。
• Scope and Mechanistic Study of the Coupling Reaction of α,β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways
  作者：Ki-Hyeok Kwon、Do W. Lee、Chae S. Yi

  DOI：10.1021/om201190v

  日期：2012.1.9

  intermolecular conjugate addition of simple alkenes to α,β-unsaturated carbonyl compounds to give (Z)-selective tetrasubstituted olefin products. The analogous coupling reaction of cinnamides with electron-deficient olefins led to the oxidative coupling of two olefinic C–H bonds in forming (E)-selective diene products. The intramolecular version of the coupling reaction efficiently produced indene and bicyclic fulvene

  阳离子氢化钌络合物 [(C 6 H 6 )(PCy 3 )(CO)RuH] + BF 4 – ( 1 ) 被发现是简单烯烃与 α,β- 分子间共轭加成的高效催化剂。不饱和羰基化合物，得到( Z )-选择性四取代烯烃产物。肉桂酰胺与缺电子烯烃的类似偶联反应导致两个烯属C-H键氧化偶联，形成( E )-选择性二烯产物。偶联反应的分子内形式有效地产生了茚和双环富烯衍生物。肉桂酸乙酯与丙烯的偶联反应的经验速率定律确定如下：速率= k [ 1 ] 1 [丙烯] 0 [肉桂酸酯] -1。从 ( E )-C 6 H 5 CH=C(CH 3 ) CONHCH 3和 ( E )-C 6 H 5 CD=C测量到可忽略不计的氘动力学同位素效应 ( k H / k D = 1.1 ± 0.1) (CH 3 )CONHCH 3与苯乙烯。相反，从( E )-C 6 H 5 CH=C(CH 3 )CONHCH 3与苯乙烯和苯乙烯-d
• [EN] METHOD FOR PRODUCING -MERCAPTO CARBOXYLIC ACIDS<br/>[FR] PROCÉDÉ D'ÉLABORATION D'ACIDES BÊTA-MERCAPTO CARBOXYLIQUES
  申请人：SHOWA DENKO KK

  公开号：WO2009113711A1

  公开（公告）日：2009-09-17

  An object of the present invention is to provide a method for industrially producing beta-mercapto carboxylic acids that are useful as synthetic raw materials for medicines and agrochemicals or as additives for polymer compounds from easily available alpha,beta-unsaturated carboxylic acids in high yields and productivity. The present invention is characterized in that a solvent having an amide group and represented by the formula (1) is used when the alpha,beta-unsaturated carboxylic acids are reacted with hydrogen sulfides to produce the beta-mercapto carboxylic acids. Particularly, it is more preferable to carry out the reaction at a pH range of 6.0 to 8.5: (In the formula (1), R1 represents any one of a hydrogen atom, an alkoxy group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an amino group, and an alkylamino group having 1 to 5 carbon atoms; R2 and R3 each represents independently any one of a hydrogen atom and an alkyl group having 1 to 5 carbon atoms; when both R2 and R3 are not a hydrogen atom, R2 and R3 may together form a ring structure through an alkylene group; and when both R1 and R2 are not a hydrogen atom, R1 and R2 may form a ring structure through an alkylene group).

  本发明的目的是提供一种工业生产β-巯基羧酸的方法，该方法可以从易得到的α，β-不饱和羧酸高产高效地合成用于药品和农药的合成原料或聚合物化合物的添加剂。本发明的特点在于，在α，β-不饱和羧酸与氢硫化物反应产生β-巯基羧酸时，使用具有酰胺基的溶剂，该溶剂由公式（1）表示。特别是，在pH范围为6.0至8.5的条件下进行反应更为理想：（在公式（1）中，R1代表氢原子、具有1至5个碳原子的烷氧基、具有1至5个碳原子的烷基、氨基和具有1至5个碳原子的烷基氨基中的任意一种；R2和R3各自独立地代表氢原子和具有1至5个碳原子的烷基中的任意一种；当R2和R3均不是氢原子时，R2和R3可以通过烷基链结构形成环状结构；当R1和R2均不是氢原子时，R1和R2可以通过烷基链结构形成环状结构。）