N-[1-(4-methylphenyl)ethyl]phthalimide | 101207-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-[1-(4-methylphenyl)ethyl]phthalimide
• 英文别名: 2-(1-(p-tolyl)ethyl)isoindoline-1,3-dione；N-(1-p-tolyl-ethyl)-phthalimide；4-(1-phthalimidoethyl)toluene；2-[1-(4-methylphenyl)ethyl]isoindole-1,3-dione
• CAS: 101207-49-2
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: RGRNZPMALLCOIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[1-(4-methyl-phenyl)-vinyl]-isoindole-1,3-dione 在 Ru[(R_PS_C)-TangPhos](NBD)SbF₆ 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、3.04 MPa 条件下， 反应 18.0h， 生成 N-[1-(4-methylphenyl)ethyl]phthalimide
  参考文献：
  名称：

  Highly enantioselective hydrogenation of N-phthaloyl enamides

  摘要：

  Rh- or Ru-catalyzed highly enantioselective hydrogenation of N-phthaloyl enamides is presented. Electron-rich Tang-Phos and DuanPhos are found to be effective ligands for Rh-catalyzed hydrogenation of alpha-aryl enamides and up to 99% ee has been achieved. In contrast, for the hydrogenation of alpha-alkyl enamide.. the Ru-C-3-TunePhos complex is more effective and up to 69% ee can be observed. This work is the first report of the hydrogenation of N-phthaloyl enamides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.064

文献信息

• Amidine derivatives and cardiotonic compositions
  申请人：Torii & Co. Ltd.

  公开号：US04598077A1

  公开（公告）日：1986-07-01

  Amidine derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent each a hydrogen atom or a lower alkyl group, or R.sub.1 and R.sub.2 together with an intermediary carbon atom and/or hetero atom may form a ring; X represents ##STR2## (wherein R.sub.8 represents a hydrogen atom, a lower alkyl group, or --CH.sub.2 COOR.sub.9, where R.sub.9 represents a hydrogen atom or a lower alkyl group; Z represents a single bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, or --CH.dbd.CH--); R.sub.3 represents a hydrogen or chlorine atom, methoxy group, nitro group, or amino group; Y represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 O--, or --OCH.sub.2 --; R.sub.4 represents a hydrogen atom, methoxy group, benzoyl group, nitro group, or amino group; and R.sub.5, R.sub.6 and R.sub.7, which may be the same or different, represent each a hydrogen atom, lower alkyl group, cycloalkyl group, aralkyl group, substituted alkyl group, substituted aralkyl group, or amino group, or R.sub.5 and R.sub.7 may form a ring, or salts thereof have an excellent cardiotonic activity and can be used as cardiotonics.

  式##STR1##中的胺基衍生物，其中R.sub.1和R.sub.2，可以相同也可以不同，分别代表氢原子或低碳基团，或者R.sub.1和R.sub.2与中间的碳原子和/或杂原子一起可以形成环；X代表##STR2##（其中R.sub.8代表氢原子、低碳基团，或--CH.sub.2 COOR.sub.9，其中R.sub.9代表氢原子或低碳基团；Z代表单键，--CH.sub.2 --，--CH.sub.2 CH.sub.2 --，或--CH.dbd.CH--）；R.sub.3代表氢或氯原子，甲氧基，硝基，或氨基；Y代表--CH.sub.2 CH.sub.2 --，--CH.dbd.CH--，--CH.sub.2 O--，或--OCH.sub.2 --；R.sub.4代表氢原子，甲氧基，苯甲酰基，硝基，或氨基；以及R.sub.5，R.sub.6和R.sub.7，可以相同也可以不同，分别代表氢原子，低碳基团，环烷基团，芳基烷基团，取代基烷基团，取代基芳基烷基团，或氨基，或者R.sub.5和R.sub.7可以形成环，或其盐具有优异的心力活性，并可用作心力药。
• 1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents
  作者：Jakub Adamek、Roman Mazurkiewicz、Anna Węgrzyk、Karol Erfurt

  DOI：10.3762/bjoc.13.142

  日期：——

  imidoalkylating properties of the obtained 1-imidoalkylphosphonium salts were tested using the Tscherniac-Einhorn-type reaction with aromatic hydrocarbons as a model reaction. It was found that the Cα-P+ bond strength can be considerably reduced and the imidoalkylation of arenes can be markedly facilitated using 1-imidoalkylphosphonium salts derived from triarylphosphines with electron-withdrawing substituents

  在已报道的研究中，开发了迄今为止未知的1-亚氨基烷基phosph盐的有效合成方法。该方法的关键步骤包括将N-邻苯二甲酰基-或N-琥珀酰氨基酸脱羧化α-甲氧基化为相应的N-（1-甲氧基烷基）酰亚胺，然后通过三芳基phosph的熔融将甲氧基取代为三芳基phosph基。酰亚胺衍生物与四氟硼酸三芳基phosph。使用Tscherniac-Einhorn型反应和芳香族烃作为模型反应，测试了所获得的1-亚氨基烷基phosph盐的亚氨基烷基化性质。发现使用衍生自具有吸电子取代基的三芳基膦的1-亚氨基烷基phosph盐如三（间-氯苯基）膦，三（对-苯基），可以显着降低Cα-P+键的强度，并显着促进芳烃的亚氨基烷基化。氯苯基）膦和三[对-（三氟甲基）苯基]膦。微波辐射还大大促进了高极性Cα-P+键的裂解。
• Iridium-Catalyzed Hydroiodination and Formal Hydroamination of Olefins with <i>N-</i>Iodo Reagents and Molecular Hydrogen: An Umpolung Strategy
  作者：Huaxin Yang、Yang Zhou、Zhihan Zhang、Jialin Wen、Xumu Zhang

  DOI：10.1021/acs.orglett.2c00392

  日期：2022.3.11

  We herein report a convenient method to convert olefins to organic iodides and amines using an Ir/ZhaoPhos catalyst, molecular hydrogen, and an electrophilic iodine(I) reagent. High yields and regioselectivities were obtained under mild conditions. In addition, basic workup with potassium carbonate leads to C–N products. Control experiments and DFT calculations tentatively excluded the pathway involving

  我们在此报告了一种使用 Ir/ZhaoPhos 催化剂、分子氢和亲电子碘 (I) 试剂将烯烃转化为有机碘化物和胺的简便方法。在温和条件下获得了高产率和区域选择性。此外，用碳酸钾进行碱性后处理会产生 C-N 产物。对照实验和 DFT 计算暂时排除了涉及HI原位形成的途径。相反，提出了一种涉及氢化卤离子中间体的催化循环。
• Iridium-catalyzed asymmetric addition of imides to alkenes
  作者：Kentaro Yamakawa、Kana Sakamoto、Takahiro Nishimura

  DOI：10.1039/d3cc04406h

  日期：——

  Enantioselective addition of an imide N–H bond to alkenes was realized by use of a cationic iridium catalyst. Bulky diphosphine ligands such as DTBM-segphos, DTBM-MeO-biphep, and DTBM-binap were indispensable for the reaction. A variety of styrene derivatives, allylsilanes, and norbornene were good substrates to give the corresponding chiral adducts with high enantioselectivity.

  通过使用阳离子铱催化剂，实现了酰亚胺 N-H 键与烯烃的对映选择性加成。DTBM-segphos、DTBM-MeO-biphep 和 DTBM-binap 等大体积二膦配体对于该反应是不可或缺的。各种苯乙烯衍生物、烯丙基硅烷和降冰片烯是良好的底物，可以得到具有高对映选择性的相应手性加合物。
• US4598077A
  申请人：——

  公开号：US4598077A

  公开（公告）日：1986-07-01