β-Methylcinnamonylmethylamin | 91132-09-1

• 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: β-Methylcinnamonylmethylamin
• 英文别名: N-methyl-3-phenylbut-2-enamide
• CAS: 91132-09-1
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: SCSDQNZYSLRNHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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

• 作为产物：
  描述：

  N-methoxy-N-methyl-3-phenylbut-2-enamide 在 蒽 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以82%的产率得到β-Methylcinnamonylmethylamin
  参考文献：
  名称：

  Weinreb 酰胺的有机光催化 N-O 键断裂：从 PET 到 ConPET 平台的机制引导进化

  摘要：

  Weinreb 酰胺的温和、有机光催化 N-O 键裂解，从而将这一古老基序的化学扩展到酰化之外。这种氧化还原中性过程开始调和当代合成中普遍存在的 N-O 键与键断裂通常所需的不成比例的苛刻化学计量条件。该策略与母体烷基衍生物（N-OMe、N-OAlkyl）兼容，从而补充了定制的O- 需要 N-OAr 基团的取代基方法（Ar = 缺电子）。公开了广泛的无环和环状衍生物（>40 个实例，高达 95%），并且该方法的合成效用在一系列应用中得到证明。在环状 Weinreb 酰胺衍生物的情况下，该平台能够在一次转化中生成不同链长的两亲酰胺醛。受 Emil Fischer 1908 年使用钠汞齐合成氨基乙醛的开创性启发，这种方法提供了一种更温和的途径来获得这类重要的材料。机械引导的反应发展证明了光诱导电子转移 (PET) 机制的参与，这已进一步发展为连续光诱导电子转移 (ConPET) 歧管：

  DOI：

  10.1021/acscatal.2c02991

文献信息

• [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。）
• METHOD FOR PRODUCING BETA-MERCAPTO CARBOXYLIC ACIDS
  申请人：Showa Denko K.K.

  公开号：EP2268614B1

  公开（公告）日：2013-05-15
• METHOD FOR PRODUCING BETA-MERCAPTO CARBOXYLIC ACIDS
  申请人：Aoki Hidemasa

  公开号：US20110015436A1

  公开（公告）日：2011-01-20

  An object of the present invention is to provide a method for industrially producing β-mercapto carboxylic acids that are useful as synthetic raw materials for medicines and agrochemicals or as additives for polymer compounds from easily available α,β-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 α,β-unsaturated carboxylic acids are reacted with hydrogen sulfides to produce the β-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), R 1 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; R 2 and R 3 each represents independently any one of a hydrogen atom and an alkyl group having 1 to 5 carbon atoms; when both R 2 and R 3 are not a hydrogen atom, R 2 and R 3 may together form a ring structure through an alkylene group; and when both R 1 and R 2 are not a hydrogen atom, R 1 and R 2 may form a ring structure through an alkylene group).
• US8258340B2
  申请人：——

  公开号：US8258340B2

  公开（公告）日：2012-09-04
• Organophotocatalytic N–O Bond Cleavage of Weinreb Amides: Mechanism-Guided Evolution of a PET to ConPET Platform
  作者：Julia Soika、Calum McLaughlin、Tomáš Neveselý、Constantin G. Daniliuc、John. J. Molloy、Ryan Gilmour

  DOI：10.1021/acscatal.2c02991

  日期：2022.8.19

  A mild, organophotocatalytic N–O bond cleavage of Weinreb amides is disclosed, thereby expanding the chemistry of this venerable motif beyond acylation. This redox neutral process begins to reconcile the ubiquity of N–O bonds in contemporary synthesis with the disproportionately harsh, stoichiometric conditions that are often required for bond cleavage. The strategy is compatible with the parent alkyl

  Weinreb 酰胺的温和、有机光催化 N-O 键裂解，从而将这一古老基序的化学扩展到酰化之外。这种氧化还原中性过程开始调和当代合成中普遍存在的 N-O 键与键断裂通常所需的不成比例的苛刻化学计量条件。该策略与母体烷基衍生物（N-OMe、N-OAlkyl）兼容，从而补充了定制的O- 需要 N-OAr 基团的取代基方法（Ar = 缺电子）。公开了广泛的无环和环状衍生物（>40 个实例，高达 95%），并且该方法的合成效用在一系列应用中得到证明。在环状 Weinreb 酰胺衍生物的情况下，该平台能够在一次转化中生成不同链长的两亲酰胺醛。受 Emil Fischer 1908 年使用钠汞齐合成氨基乙醛的开创性启发，这种方法提供了一种更温和的途径来获得这类重要的材料。机械引导的反应发展证明了光诱导电子转移 (PET) 机制的参与，这已进一步发展为连续光诱导电子转移 (ConPET) 歧管：