2-[2-氧代-2-[4-(三氟甲基)苯基]乙基]异吲哚-1,3-二酮 | 391-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-[2-氧代-2-[4-(三氟甲基)苯基]乙基]异吲哚-1,3-二酮
• 英文名称: N-(4-trifluoromethyl-phenacyl)-phthalimide
• 英文别名: N-(4-Trifluormethyl-phenacyl)-phthalimid；2-[2-Oxo-2-[4-(trifluoromethyl)phenyl]ethyl]isoindole-1,3-dione
• CAS: 391-10-6
• 化学式: C₁₇H₁₀F₃NO₃
• 分子量: 333.267
• InChiKey: YCTRFLJIVGYLTG-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C
• 沸点：
  460.5±45.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2-氧代-2-[4-(三氟甲基)苯基]乙基]异吲哚-1,3-二酮 在 盐酸 、 氢氧化钾 作用下， 生成 2-氨基-1-[4-(三氟甲基)苯基]乙酮
  参考文献：
  名称：

  The Synthesis of an Analog of Chloramphenicol¹

  摘要：

  DOI：

  10.1021/ja01119a029
• 作为产物：
  描述：

  4'-三氟甲基苯乙酮 在 溴 、 N,N-二甲基甲酰胺 作用下， 生成 2-[2-氧代-2-[4-(三氟甲基)苯基]乙基]异吲哚-1,3-二酮
  参考文献：
  名称：

  The Synthesis of an Analog of Chloramphenicol¹

  摘要：

  DOI：

  10.1021/ja01119a029

文献信息

• Convergent routes to substituted naphthylamides
  作者：Ngoc Diem My Tran、Samir Z. Zard

  DOI：10.1039/c4ob00339j

  日期：——

  Practical, convergent routes to variously substituted 1- and 2-naphthylamides have been developed. They exploit the ability of xanthates to undergo both intermolecular radical additions to vinyl pivalate and intramolecular radical cyclisations to aromatic rings. In the case of 1-naphthylamides, the existence of an intramolecular hydrogen bond was used to facilitate the cyclisation step.

  我们开发出了获得各种取代的 1-和 2-萘酰胺的实用趋同路线。它们利用了黄原酸盐分子间自由基加成新戊酸乙烯酯和分子内自由基环化芳香环的能力。就 1-萘甲酰胺而言，分子内氢键的存在被用来促进环化步骤。
• New anticancer agents: synthesis of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza-7,8-dihydropteridines)
  作者：Carroll Temple、Glynn P. Wheeler、Robert D. Elliott、Jerry D. Rose、Conrad L. Kussner、Robert N. Comber、John A. Montgomery

  DOI：10.1021/jm00351a008

  日期：1982.9

  Reaction of alpha-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-[(2-oxo-2-phenylethyl)amino]pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4). Related pyridines substituted with a keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4- [[3-(N-methyl-N-phenylamino)-2-hydroxypropyl]amino]-5-nitropyridine-7- carbamates (6). Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7). Several of the oximes 3 were successfully hydrogenated to give 7 directly. The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice. These biological activities are attributed to the accumulation of cells at mitosis.
• The Synthesis of an Analog of Chloramphenicol¹
  作者：William T. Caldwell、George C. Schweiker

  DOI：10.1021/ja01119a029

  日期：1953.12