N-(S)-(-)-α-Methylbenzylmaleimide | 6129-15-3

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(S)-(-)-α-Methylbenzylmaleimide
• 英文别名: 1-(1-phenylethyl)-1H-pyrrole-2,5-dione；d,l-N-α-Methylbenzylmaleimide；N-(α)-methylbenzylmaleimide；N-(α-Methylbenzyl)maleimide；N-(1-phenylethyl)maleimide；(R)-(+)-N-α-methylbenzylmaleimide；1H-Pyrrole-2,5-dione, 1-(1-phenylethyl)-；1-(1-phenylethyl)pyrrole-2,5-dione
• CAS: 6129-15-3；60925-76-0；94132-27-1；89143-10-2
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD00458390
• 分子量: 201.225
• InChiKey: PWZXUQWQRVKGAH-UHFFFAOYSA-N

物化性质

• 沸点：
  110-115 °C/0.004 mmHg (lit.)
• 密度：
  1.138 g/mL at 25 °C (lit.)
• 闪点：
  113 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36
• WGK Germany：
  3

制备方法与用途

本品为一种光学活性物质，能与苯乙烯发生自由基共聚合反应，生成约1:1的共聚物（占比达98%）。这种具有非对称主链的乙烯基共聚物可用作非线性光学材料，并且是用于非对映选择性Diels-Alder反应的良好亲二烯体。

反应信息

• 作为反应物：
  描述：

  N-(S)-(-)-α-Methylbenzylmaleimide 、 天然橡胶 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Diastereoselective diels-alder reactions between substituted 1,3-butadienes and n-α-methylbenzylmaleimide

  摘要：

  The TiCl4 catalyzed reaction between 2-t-butyl-1,3-butadiene and N-alpha-methylbenzylmaleimide at -65-degrees-C affords diastereomeric Diels-Alder adducts in a 15:1 ratio. The structure of the major adduct was determined by x-ray.

  DOI：

  10.1016/s0040-4039(00)79415-9
• 作为产物：
  描述：

  4-Oxo-4-[(1-phenylethyl)amino]but-2-enoic acid 在 sodium acetate 、 乙酸酐 作用下， 以1.13 g的产率得到N-(S)-(-)-α-Methylbenzylmaleimide
  参考文献：
  名称：

  Tailor‐Made Pd _n L _{2 n} Metal‐Organic Cages through Covalent Post‐Synthetic Modification

  摘要：

  AbstractPost‐synthetic modification (PSM) is an effective approach for the tailored functionalization of metal‐organic architectures, but its generalizability remains challenging. Herein we report a general covalent PSM strategy to functionalize PdnL2n metal‐organic cages (MOCs, n=2, 12) through an efficient Diels–Alder cycloaddition between peripheral anthracene substituents and various functional motifs bearing a maleimide group. As expected, the solubility of functionalized Pd12L24 in common solvents can be greatly improved. Interestingly, concentration‐dependent circular dichroism and aggregation‐induced emission are achieved with chiral binaphthol (BINOL)‐ and tetraphenylethylene‐modified Pd12L24, respectively. Furthermore, Pd12L24 can be introduced with two different functional groups (e.g., chiral BINOL and achiral pyrene) through a step‐by‐step PSM route to obtain chirality‐induced circularly polarized luminescence. Moreover, similar results are readily observed with a smaller Pd2L4 system.

  DOI：

  10.1002/anie.202216977

文献信息

• Breaking Symmetry with Symmetry: Bifacial Selectivity in the Asymmetric Cycloaddition of Anthracene Derivatives
  作者：Carles Rodríguez-Escrich、Rebecca L. Davis、Hao Jiang、Julian Stiller、Tore K. Johansen、Karl Anker Jørgensen

  DOI：10.1002/chem.201300142

  日期：2013.2.25

  Push to activate: A new catalytic strategy for the activation of anthracene derivatives has been developed. From symmetrical starting materials, enantioselective cycloaddition reactions can be achieved by employing a C2‐symmetric aminocatalyst. This selectivity is due to the gain or loss of conjugation between the enamine and the anthracene in the two transition‐state structures. This methodology is demonstrated

  推动活化：已开发出用于活化蒽衍生物的新催化策略。从对称的起始原料，可以通过使用C 2对称的氨基催化剂来实现对映选择性的环加成反应。这种选择性是由于两个过渡态结构中烯胺和蒽之间共轭的得失所致。在14个示例中证明了该方法，其产率为70-96％，ee为76-95％  。
• Aerobic Oxidative EDA Catalysis: Synthesis of Tetrahydroquinolines Using an Organocatalytic EDA Active Acceptor
  作者：August Runemark、Henrik Sundén

  DOI：10.1021/acs.joc.1c02776

  日期：2022.1.21

  A catalytic electron donor–acceptor (EDA) complex for the visible-light-driven annulation reaction between activated alkenes and N,N-substituted dialkyl anilines is reported. The key photoactive complex is formed in situ between dialkylated anilines as donors and 1,2-dibenzoylethylene as a catalytic acceptor. The catalytic acceptor is regenerated by aerobic oxidation. Investigations into the mechanism

  报道了一种催化电子供体-受体（EDA）复合物，用于活化烯烃和 N,N-取代的二烷基苯胺之间可见光驱动的环化反应。关键的光活性络合物是在作为供体的二烷基苯胺和作为催化受体的1,2-二苯甲酰乙烯之间原位形成的。催化受体通过有氧氧化再生。对该机制进行了研究，揭示了光活性 EDA 复合物中催化受体的罕见例子，该复合物可以在温和的光化学条件下实现芳香胺的选择性官能化。
• Substituted heterocyclic derivatives useful as antidiabetic and antiobesity agents and method
  申请人：——

  公开号：US20040063700A1

  公开（公告）日：2004-04-01

  1 wherein Z 1 is (CH 2 ) q or C═O; Z 2 is (CH 2 ) p or C═O; D is —CH═ or C═O or (CH 2 ) m where m is 0, 1, 2 or 3; n=0, 1 or 2; p=1 or 2; q=0, 1 or 2; Q is C or N; A is (CH 2 ) x where x is 1 to 5, or A is (CH 2 ) x 1 , where x 1 is 1 to 5 with an alkenyl bond or an alkynyl bond embedded anywhere in the chain, or A is —(CH 2 ) x 2 —O—(CH 2 ) x 2 — where x 2 is 0 to 5 and x 3 is 0 to 5, provided that at least one of x 2 and x 3 is other than 0; B is a bond or is (CH 2 ) x 4 where X 4 is 1 to 5; X is CH or N; X 2 is C, N, O or S; X 3 is C, N, O or S; X 4 i s C, N, O or S; X 5 is C, N, O or S; X 6 is C, N, O or S; provided that at least one of X 2 , X 3 , X 4 X 5 and X 6 is N; and at least one of X 2 , X 3 , X 4 X 5 and X 6 is C. R 1 is H or alkyl; R 2 is H, alkyl, alkoxy, halogen, amino, substituted amino or cyano; R 2a , R 2b and R 2c may be the same or different and are selected from H, alkyl, alkoxy, halogen, amino, substituted amino or cyano; and R 3 , E, Z and Y are as defined herein.

  其中Z1为(CH2)q或C═O；Z2为(CH2)p或C═O；D为—CH═或C═O或(CH2)m，其中m为0、1、2或3；n为0、1或2；p为1或2；q为0、1或2；Q为C或N；A为(CH2)x，其中x为1至5，或A为(CH2)x1，其中x1为带有烯丙基键或炔基键的1至5链，或A为—(CH2)x2—O—(CH2)x2—，其中x2为0至5，x3为0至5，但至少有一个x2和x3不为0；B为键或(CH2)x4，其中x4为1至5；X为CH或N；X2、X3、X4、X5和X6为C、N、O或S，但至少有一个X2、X3、X4、X5和X6为N，至少有一个X2、X3、X4、X5和X6为C；R1为H或烷基；R2为H、烷基、烷氧基、卤素、氨基、取代氨基或氰基；R2a、R2b和R2c可以相同也可以不同，选自H、烷基、烷氧基、卤素、氨基、取代氨基或氰基；R3、E、Z和Y的定义如前所述。
• SUBSTITUTED HETEROCYCLIC DERIVATIVES USEFUL AS ANTIDIABETIC AND ANTIOBESITY AGENTS AND METHOD
  申请人：Cheng T. W. Peter

  公开号：US20070287713A1

  公开（公告）日：2007-12-13

  wherein Z 1 is (CH 2 ) q or C═O; Z 2 is (CH 2 ) p or C═O; D is —CH═ or C═O or (CH 2 ) m where m is 0, 1, 2 or 3; n=0, 1 or 2; p=1 or 2; q=0, 1 or 2; Q is C or N; A is (CH 2 ) x where x is 1 to 5, or A is (CH 2 ) x 1 , where x 1 is 1 to 5 with an alkenyl bond or an alkynyl bond embedded anywhere in the chain, or A is —(CH 2 ) x 2 —O—(CH 2 ) x 3 — where x 2 is 0 to 5 and x 3 is 0 to 5, provided that at least one of x 2 and x 3 is other than 0; B is a bond or is (CH 2 ) x 4 where x 4 is 1 to 5; X is CH or N; X 2 is C, N, O or S; X 3 is C, N, O or S; X 4 is C, N, O or S; X 5 is C, N, O or S; X 6 is C, N, O or S; provided that at least one of X 2 , X 3 , X 4 X 5 and X 6 is N; and at least one of X 2 , X 3 , X 4 X 5 and X 6 is C. R 1 is H or alkyl; R 2 is H, alkyl, alkoxy, halogen, amino, substituted amino or cyano; R 2a , R 2b and R 2c may be the same or different and are selected from H, alkyl, alkoxy, halogen, amino, substituted amino or cyano; and R 3 , E, Z and Y are as defined herein.

  其中Z1为(CH2)q或C═O；Z2为(CH2)p或C═O；D为—CH═或C═O或(CH2)m，其中m为0、1、2或3；n=0、1或2；p=1或2；q=0、1或2；Q为C或N；A为(CH2)x，其中x为1到5，或A为(CH2)x1，其中x1为1到5，具有烯丙基键或炔基键嵌入链中的任何位置，或A为—(CH2)x2—O—(CH2)x3—，其中x2为0到5，x3为0到5，前提是x2和x3中至少有一个不为0；B为键或(CH2)x4，其中x4为1到5；X为CH或N；X2、X3、X4、X5和X6为C、N、O或S；前提是X2、X3、X4、X5和X6中至少有一个为N；并且X2、X3、X4、X5和X6中至少有一个为C。R1为H或烷基；R2为H、烷基、烷氧基、卤素、氨基、取代氨基或氰基；R2a、R2b和R2c可以相同也可以不同，选择自H、烷基、烷氧基、卤素、氨基、取代氨基或氰基；而R3、E、Z和Y的定义如前所述。
• NANOCOMPOSITE AND DISPERSION COMPRISING THE SAME
  申请人：Morishita Takuya

  公开号：US20120053288A1

  公开（公告）日：2012-03-01

  A nanocomposite comprises a nanostructure, and a copolymer adsorbed to the nanostructure and containing at least one ionic monomer unit and a different monomer unit from the ionic monomer unit; the ionic monomer unit selected from the group consisting of a zwitterionic monomer unit and a cationic monomer unit which are represented by the following formula (1): (in the formula (1), R 1 , R 2 , and R 3 each independently represent any one of a hydrogen atom and a monovalent organic group having 1 to 20 carbon atoms, Y 1 represents any one of a carbonyl group and an arylene group, Y 2 represents any one of —O— and —NH—, n is 0 or 1, R 4 represents a divalent organic group having 1 to 20 carbon atoms, and X represents any one of a zwitterionic group and a cationic group).

  一种纳米复合材料包括纳米结构和吸附在纳米结构上的共聚物，该共聚物包含至少一个离子单体单元和一个不同于离子单体单元的单体单元；所述离子单体单元选自以下公式（1）表示的带电单体单元组中的具有两性离子单体单元和阳离子单体单元：（在公式（1）中，R1、R2和R3各自独立地表示氢原子和具有1到20个碳原子的一价有机基团，Y1表示羰基基团和芳基基团中的任意一种，Y2表示-O-和-NH-中的任意一种，n为0或1，R4表示具有1到20个碳原子的二价有机基团，X表示具有两性离子基团和阳离子基团中的任意一种）。