1-acetyl-3-phenylindoline | 182165-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-acetyl-3-phenylindoline
• 英文别名: 1-(3-phenylindolin-1-yl)ethan-1-one；1-(3-phenylindolin-1-yl)ethanone；N-acetyl-3-phenylindoline；1-acetyl-3-phenyl-2,3-dihydro-indole；N-Acetyl-3-phenyl-indolin；1-(3-phenyl-2,3-dihydroindol-1-yl)ethanone
• CAS: 182165-50-0
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: MDIIJQXXDHPKAC-UHFFFAOYSA-N

物化性质

• 熔点：
  52-58 °C
• 沸点：
  418.508±34.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.157±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-acetyl-3-phenylindoline 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以89%的产率得到1-acetyl-3-phenylindole
  参考文献：
  名称：

  1,3-环己二酮和硝基烯烃通过简便的芳构化反应合成多取代的6-烷氧基吲哚

  摘要：

  由1，3-环己二酮烯醇醚和β-硝基苯乙烯有效地制备了6-烷氧基-3-芳基吲哚。使用动力学生成的烯醇化物进行迈克尔加成，然后将所得加合物的硝基进行锌还原，生成了硝酮，然后将其用乙酸酐处理，通过脱水和N-乙酰化诱导芳构化，通过DDQ氧化得到所需的吲哚。该方法提供了容易进入各种多取代的6-烷氧基吲哚的方法。

  DOI：

  10.1021/jo902068m
• 作为产物：
  描述：

  1-acetyl-3-phenylindole 以100%的产率得到1-acetyl-3-phenylindoline
  参考文献：
  名称：

  Process for producing indoline compounds and intermediates for the

  摘要：

  本发明涉及一种生产代表性通式为##STR1##的3-芳基吲哚啉化合物的方法。

  公开号：

  US05936098A1

文献信息

• Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis
  作者：Sarah Z. Tasker、Timothy F. Jamison

  DOI：10.1021/jacs.5b05597

  日期：2015.8.5

  Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to perform the difficult C-N bond-forming reductive elimination, producing a Ni(I) complex, which in turn

  镍/光氧化还原催化用于从碘乙酰苯胺和烯烃一步合成二氢吲哚。对于脂肪族和苯乙烯基烯烃，3-取代二氢吲哚产物均具有非常高的区域选择性。机理研究表明，氧化为 Ni(III) 是执行困难的 CN 键形成还原消除所必需的，产生 Ni(I) 络合物，而 Ni(I) 络合物又被还原为 Ni(0)。该过程用于进一步证明光氧化还原催化剂在多氧化态镍催化中作为受控单电子转移剂的效用。
• Intermolecular dearomative C2-arylation of N-Ac indoles activated by FeCl₃
  作者：Raj Kumar Nandi、Friederike Ratsch、Rodolphe Beaud、Régis Guillot、Cyrille Kouklovsky、Guillaume Vincent

  DOI：10.1039/c6cc01654e

  日期：——

  We report the FeCl₃-mediated direct addition of electron-rich arenes to the C2-position of electrophilic N-Ac indoles under mild conditions (room temperature, air).

  我们报告了在温和条件下（室温、空气）FeCl₃介导的电子富集芳烃直接加在亲电性N-乙酰基吲哚的C2位置的反应。
• Phenylindolines
  申请人：Delmar Chemicals Limited

  公开号：US04153789A1

  公开（公告）日：1979-05-08

  The present invention is concerned with novel 2-unsubstituted-3-phenylindolines acid addition salts thereof. These compounds have been found to have valuable pharmacological properties indicative of possible utility, inter alia, of controlling coagulation of the blood and as hypoglycemic agents. The invention also provides novel processes for producing the novel compounds and pharmaceutical compositions containing same as active ingredients.

  本发明涉及新型2-未取代-3-苯基吲哚啉酸盐。这些化合物已被发现具有有价值的药理学特性，表明其可能用于控制血液凝固和作为降糖药物等方面。该发明还提供了制备这些新化合物的新型方法和含有其作为活性成分的制药组合物。
• Phenylindolines and process for their production
  申请人：Delmar Chemicals Limited

  公开号：US04080330A1

  公开（公告）日：1978-03-21

  The present invention is concerned with novel 2-unsubstituted-3-phenylindolines and acid addition salts thereof. These compounds have been found to have valuable pharmacological properties indicative of possible utility, inter alia, of controlling coagulation of the blood and as hypoglycemic agents. The invention also provides novel processes for producing the novel compounds and pharmaceutical compositions containing same as active ingredients.

  本发明涉及新型的2-未取代-3-苯基吲哚和其酸加成盐。已发现这些化合物具有有价值的药理学特性，表明其可能用于控制血液凝固和作为降糖剂等方面。本发明还提供了生产这些新型化合物的新型方法和含有它们作为活性成分的药物组合物。
• PROCESS FOR PRODUCING INDOLINE COMPOUNDS AND INTERMEDIATES FOR THE PRODUCTION OF THE SAME
  申请人：TOKYO TANABE COMPANY LIMITED

  公开号：EP0810214A1

  公开（公告）日：1997-12-03

  This invention concerns a method for the production of a 3-arylindoline compound represented by the general formula (wherein R1 represents an optionally substituted phenyl group or an aromatic heterocyclic group and R2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a hydroxy group, a lower alkoxy group, a carbamoyl group, or a lower alkoxycarbonyl group) which is used for the production of a 1-acyl-3-arylindoline compound represented by the general formula (wherein R1 and R2 have the same meanings as defined above and R3 represents the following group) which is the 5-HT3 receptor antagonist, based on the fact that a 1-acyl-3-arylindole compound obtained by having a removable electron withdrawing group linked thereto by acylating the 1 position of a 3-arylindole compound with such an organic acid as carboxylic acid or sulfonic acid easily undergoes a catalytic reduction under neutral or acidic conditions and gives rise to a 1-acyl-3-arylindoline compound and that an optically active 1-acyl-3-arylindole compound obtained by the acylation with an organic acid such as optically active carboxylic acid or sulfonic acid produces an optically active 1-acyl-3-arylindoline compound with high selectivity by the reaction of a catalytic reduction.

  本发明涉及一种生产通式如下的 3-芳基吲哚啉化合物的方法 (其中 R1 代表任选取代的苯基或芳香杂环基团，R2 代表氢原子、卤素原子、低级烷基、羟基、低级烷氧基、氨基甲酰基或低级烷氧羰基）的方法，该方法用于生产由通式表示的 1-酰基-3-芳基吲哚啉化合物。 (其中 R1 和 R2 的含义与上述定义相同，R3 代表下列基团） 是 5-HT3 受体拮抗剂、通过用羧酸或磺酸等有机酸对 3-芳基吲哚化合物的 1 位进行酰化而得到的 1-酰基-3-芳基吲哚化合物，在中性或酸性条件下很容易发生催化还原反应，生成 1-酰基-3-芳基吲哚化合物。3-芳基吲哚化合物，而通过与有机酸（如具有光学活性的羧酸或磺酸）酰化得到的具有光学活性的 1-酰基-3-芳基吲哚化合物通过催化还原反应以高选择性生成具有光学活性的 1-酰基-3-芳基吲哚化合物。