2-[2-(2-Methylphenyl)ethyl]isoindole-1,3-dione | 117661-73-1

• 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: 2-[2-(2-Methylphenyl)ethyl]isoindole-1,3-dione
• CAS: 117661-73-1
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: GMVKTAJAVHPXIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：

  2-[2-(2-Methylphenyl)ethyl]isoindole-1,3-dione 以 乙腈 为溶剂， 反应 7.0h， 以5%的产率得到13a-Hydroxy-7,8,13,13a-tetrahydro-benzo[4,5]azepino[2,1-a]isoindol-5-one
  参考文献：
  名称：

  Photoreaction of Phthalimides Possessing an ortho-Methylphenyl Group in Their N-Side Chain. Synthesis of Tetracyclic Nitrogen Heterocycles

  摘要：

  DOI：

  10.3987/r-1987-10-2683
• 作为产物：
  描述：

  邻甲基氯化苄 在 sodium tetrahydroborate 、 苄基三乙基氯化铵 、 三氟乙酸 作用下， 以 水 、 苯 为溶剂， 生成 2-[2-(2-Methylphenyl)ethyl]isoindole-1,3-dione
  参考文献：
  名称：

  Photoreaction of Phthalimides Possessing an ortho-Methylphenyl Group in Their N-Side Chain. Synthesis of Tetracyclic Nitrogen Heterocycles

  摘要：

  DOI：

  10.3987/r-1987-10-2683

文献信息

• Benzylphthalimides and Phenethylphthalimides with Thalidomide-Like Activity on the Production of Tumor Necrosis Factor .ALPHA..
  作者：Keizo SASAKI、Yoshihiro SHIBATA、Yuichi HASHIMOTO、Shigeo IWASAKI

  DOI：10.1248/bpb.18.1228

  日期：——

  Benzylphthalimide analogs (P1P's) and phenethylphthalimide analogs (P2P's) have been found to exhibit thalidomide-like activity on the production of tumor necrosis factor (TNF)-α by the human leukemia cell line, HL-60, stimulated by 12-O-tetradecanoylphorbol-13-acetate (TPA). Structure-activity relationships are discussed on the basis of the TNF-α production-enhancing activity. Benzylphthalimide (P1P-00) exhibited activity which is weaker than that of thalidomide, but introduction of a methyl group at the ortho-position of the benzyl moiety (P1P-10) resulted an increase to a level comparable with that of thalidomide. Phenethylphthalimide (P2P-00) is more potent than thalidomide, and its fluorinated derivative, 2-phenethyl-4, 5, 6, 7-tetrafluoro-1H-isoindole-1, 3-dione (FP2P-00), exhibited potent activity at very low concentrations.

  苄基邻苯二甲酰亚胺类化合物（P1P's）和苯乙基邻苯二甲酰亚胺类化合物（P2P's）被发现能够在通过12-O-十四酸酯磷酸酯（TPA）刺激的人类白血病细胞系HL-60中表现出类沙利度胺的活性，促进肿瘤坏死因子（TNF）-α的产生。基于TNF-α产生增强活性，讨论了结构-活性关系。苄基邻苯二甲酰亚胺（P1P-00）表现出的活性弱于沙利度胺，但在苄基的邻位引入甲基（P1P-10）后，其活性增强至与沙利度胺相当的水平。苯乙基邻苯二甲酰亚胺（P2P-00）的活性比沙利度胺更强，其氟化衍生物2-苯乙基-4, 5, 6, 7-四氟-1H-异苯并吡咯-1, 3-二酮（FP2P-00）在极低浓度下表现出强效活性。
• 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.
• Oda, Kazuaki; Yoshida, Eiichi; Ohno, Kosei, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 3, p. 642 - 647
  作者：Oda, Kazuaki、Yoshida, Eiichi、Ohno, Kosei、Machida, Minoru、Kanaoka, Yuichi

  DOI：——

  日期：——
• ODA, KAZUAKI;YOSHIDA, EIICHI;OHNO, KOSEI;MACHIDA, MINORU;KANAOKA, YUICHI, CHEM. PHARM. BULL., 37,(1989) N, C. 642-647
  作者：ODA, KAZUAKI、YOSHIDA, EIICHI、OHNO, KOSEI、MACHIDA, MINORU、KANAOKA, YUICHI

  DOI：——

  日期：——