N-[2-(3-methyl-phenyl)ethyl]-phthalimide | 1000563-21-2

• 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-[2-(3-methyl-phenyl)ethyl]-phthalimide
• 英文别名: 2-[2-(3-Methylphenyl)ethyl]isoindole-1,3-dione；2-[2-(3-methylphenyl)ethyl]isoindole-1,3-dione
• CAS: 1000563-21-2
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: TWGUVZXZNBLHCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  N-[2-(3-methyl-phenyl)ethyl]-phthalimide 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到12b-hydroxy-3-methyl-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one
  参考文献：
  名称：

  Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine

  摘要：

  用三氟甲磺酸活化酰亚胺羰基有助于苯乙基邻苯二甲酰亚胺的分子内环化，从而得到融合的异吲哚异喹啉酮骨架。利用这种方法，首次成功地进行了异吲哚异喹啉酮生物碱 (±)-nuevamine 的一锅区域选择性合成。

  DOI：

  10.1039/c1ob06349a
• 作为产物：
  描述：

  苯酐 、 间甲基苯乙胺 以 甲苯 为溶剂， 以83%的产率得到N-[2-(3-methyl-phenyl)ethyl]-phthalimide
  参考文献：
  名称：

  Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine

  摘要：

  用三氟甲磺酸活化酰亚胺羰基有助于苯乙基邻苯二甲酰亚胺的分子内环化，从而得到融合的异吲哚异喹啉酮骨架。利用这种方法，首次成功地进行了异吲哚异喹啉酮生物碱 (±)-nuevamine 的一锅区域选择性合成。

  DOI：

  10.1039/c1ob06349a

文献信息

• Sterically Controlled Isodesmic Late-Stage C–H Iodination of Arenes
  作者：Manuel van Gemmeren、Mirxan Farizyan、Rita de Jesus、Jyotirmoy Dey

  DOI：10.1039/d3sc00801k

  日期：——

  availability of the required starting materials. Herein, we describe the sterically controlled iodination of arenes through an isodesmic C–H/C–I bond metathesis approach enabled by our dual ligand-based catalysts for arene-limited nondirected C–H activation. The protocol gives direct access to a complementary product spectrum with respect to traditional methods. Its synthetic utility is demonstrated by

  芳基碘化物是有机化学中的关键基序，因为它们在金属介导的交叉偶联反应中作为关键的多功能性，用于合成和药物发现。这些支架通常由预功能化起始材料间接制备或通过亲电芳香族碘化协议。这些方法因其固有的选择性和/或所需起始材料的可用性而限于特定的区域异构体。在此，我们描述了通过基于双配体的双配体催化剂实现的等距 C-H/C-I 键复分解方法对芳烃进行空间控制的碘化，以实现芳烃限制的非定向 C-H 活化。该协议允许直接访问与传统方法相关的互补产品谱。它的合成效用通过广泛的范围和后期修饰的适用性得到证明。
• One-Pot Cascade Trifluoromethylation/Cyclization of Imides: Synthesis of α-Trifluoromethylated Amine Derivatives
  作者：Vinay Kumar Pandey、Pazhamalai Anbarasan

  DOI：10.1021/jo5002998

  日期：2014.5.2

  Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the alpha-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.
• Synthesis and biological evaluation of isoindoloisoquinolinone, pyroloisoquinolinone and benzoquinazolinone derivatives as poly(ADP-ribose) polymerase-1 inhibitors
  作者：Arumugam Suyavaran、Chitteti Ramamurthy、Ramachandran Mareeswaran、Yagna Viswa Shanthi、Jayaraman Selvakumar、Selvaraj Mangalaraj、Muthuvel Suresh Kumar、Chinnasamy Ramaraj Ramanathan、Chinnasamy Thirunavukkarasu

  DOI：10.1016/j.bmc.2014.12.017

  日期：2015.2

  A series of novel fused isoquinolinones with isoindoloisoquinolinone, pyroloisoquinolinone, and benzoquinalizinone skeletons were synthesized from corresponding phenethylimides. The isoquinolinone derivatives were evaluated for their protective effect on chicken erythrocytes subjected to oxidative damage. The effect of isoquinolinone derivatives were analysed by estimation of cell viability, antioxidant enzyme activities, DNA damage (comet assay), PARP-1 inhibition assay and molecular docking of the compounds with PARP-1 active site. The compounds CRR-271, CRR-288 and CRR-224+225 showed significant protective effect at 100 mu M concentration. The PARP-1 inhibition assay revealed the IC50 values of CRR-271, CRR-288 and CRR-224+225 as <200 nM, further molecular docking studies shows higher binding energies with PARP-1 active site. Interesting findings in this study suggest that the novel isoquinolinone derivatives inhibit PARP-1 activity and protect cells against oxidative DNA damage, which could be implemented in the treatment of inflammatory diseases. (C) 2014 Elsevier Ltd. All rights reserved.
• Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine
  作者：Jayaraman Selvakumar、Chinnasamy Ramaraj Ramanathan

  DOI：10.1039/c1ob06349a

  日期：——

  Activation of imide carbonyl group with trifluoromethanesulfonic acid facilitates the intramolecular cyclization of phenethylphthalimides to give a fused isoindoloisoquinolinone skeleton. The first one pot regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine has been successfully executed using this methodology.

  用三氟甲磺酸活化酰亚胺羰基有助于苯乙基邻苯二甲酰亚胺的分子内环化，从而得到融合的异吲哚异喹啉酮骨架。利用这种方法，首次成功地进行了异吲哚异喹啉酮生物碱 (±)-nuevamine 的一锅区域选择性合成。