methyl benzindole-2-carboxylate | 55970-07-5

• 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: methyl benzindole-2-carboxylate
• 英文别名: methyl 1H-benzo[g]indole-2-carboxylate；2-Carbomethoxy-6,7-benzindol；2-Methoxycarbonyl-6,7-benzindol；1H-benzo[g]indole-2-carboxylic acid methyl ester；methyl benz[g]indole-2-carboxylate
• CAS: 55970-07-5
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: NFLXKEHVYVOZAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl benzindole-2-carboxylate 在 platinum(IV) oxide 氢气 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、405.3 kPa 条件下， 反应 46.0h， 生成 1H-苯并[g]吲哚-2-羧酸,5-氨基-,甲基酯
  参考文献：
  名称：

  Synthesis and characterization of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate

  摘要：

  The synthesis of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate (4), is described, and its physical and chemical properties are compared to those of the trimethyl ester of PQQ (2) and the methyl ester of 7,9-didecarboxy PQQ (3). The synthesis of 4 was achieved by starting with 1-aminonaphthalene and constructing 2-carbomethoxybenz[g]indole (7) by a Japp-Klingemann reaction with methyl alpha-methylacetoacetate and a subsequent Fischer indolization reaction. The quinone function was introduced by a Fremy's salt oxidation of 5-aminoindole 9 which was prepared from 7 by regioselective nitration and catalytic hydrogenation. From the physical properties, it can be recognized that the peri pyridine nitrogen and the ester groups at the 7- and 9-positions considerably affect the electronic nature of the molecules. This is reflected on the reactivities of the quinones in the acetone-adduct formation, the reaction with phenylhydrazine, and the aerobic autorecycling oxidation of benzylamine. The significant roles of the pyridine nitrogen and the ester groups in these reactions are discussed.

  DOI：

  10.1021/jo00036a007
• 作为产物：
  描述：

  methyl pyruvate 1-naphthylhydrazone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到methyl benzindole-2-carboxylate
  参考文献：
  名称：

  Synthesis and characterization of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate

  摘要：

  The synthesis of the 6-deaza derivative of coenzyme PQQ, methyl 4,5-dihydro-4,5-dioxobenz[g]indole-2-carboxylate (4), is described, and its physical and chemical properties are compared to those of the trimethyl ester of PQQ (2) and the methyl ester of 7,9-didecarboxy PQQ (3). The synthesis of 4 was achieved by starting with 1-aminonaphthalene and constructing 2-carbomethoxybenz[g]indole (7) by a Japp-Klingemann reaction with methyl alpha-methylacetoacetate and a subsequent Fischer indolization reaction. The quinone function was introduced by a Fremy's salt oxidation of 5-aminoindole 9 which was prepared from 7 by regioselective nitration and catalytic hydrogenation. From the physical properties, it can be recognized that the peri pyridine nitrogen and the ester groups at the 7- and 9-positions considerably affect the electronic nature of the molecules. This is reflected on the reactivities of the quinones in the acetone-adduct formation, the reaction with phenylhydrazine, and the aerobic autorecycling oxidation of benzylamine. The significant roles of the pyridine nitrogen and the ester groups in these reactions are discussed.

  DOI：

  10.1021/jo00036a007

文献信息

• Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones
  作者：Alberto V. Jerezano、Ehecatl M. Labarrios、Fabiola E. Jiménez、María del Carmen Cruz、Diana C. Pazos、Rsuini U. Gutiérrez、Francisco Delgado、Joaquín Tamariz

  DOI：10.3998/ark.5550190.p008.138

  日期：——

  The synthesis of 2-carbonylindoles was achieved via a iodine-mediated cyclization of the corresponding enaminone precursors, which were form ed by reaction of the α-arylaminomethylene carbonyl derivatives with N,N′-dimethylformamide dimethyl acetal (DMFDMA). An alternative and more efficient procedure consisted of a similar cyclization of the enaminones, but under solvent-free and grinding reaction

  2-羰基吲哚的合成是通过相应烯胺酮前体的碘介导环化来实现的，该前体是通过α-芳基氨基亚甲基羰基衍生物与N,N'-二甲基甲酰胺二甲基乙缩醛（DMFDMA）反应形成的。另一种更有效的方法包括烯胺酮的类似环化，但在无溶剂和研磨反应条件下。在另一个碘促进的过程中，通过 α-芳基氨基亚甲基羰基衍生物和 DMFDMA 之间的一锅级联反应合成了 2-羰基-3-二甲基氨基吲哚。
• Anti-aids piperazines
  申请人：The Upjohn Company

  公开号：US05489593A1

  公开（公告）日：1996-02-06

  The present invention includes diaromatic substituted heterocyclic compounds (III) ##STR1## which are useful in treating individuals infected with the HIV virus. The invention includes certain previously generically disclosed anti-AIDS piperazinyl compounds (V) and a method of treating HIV infected individuals with the indoles of formula (V) and the anti-AIDS amines (X).

  本发明包括二芳基取代的杂环化合物（III）##STR1##，其可用于治疗感染HIV病毒的个体。本发明还包括某些先前一般性披露的抗艾滋病哌嗪基化合物（V）以及一种使用吲哚类化合物（V）和抗艾滋病胺类（X）治疗HIV感染个体的方法。
• Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C−H Amination
  作者：Julien Bonnamour、Carsten Bolm

  DOI：10.1021/ol2004066

  日期：2011.4.15

  A practical iron-catalyzed intramolecular C−H amination reaction and its application in the synthesis of indole derivatives are presented. As a catalyst, commercially available iron(II) triflate is used.

  提出了一种实用的铁催化分子内胺化反应及其在吲哚衍生物合成中的应用。作为催化剂，使用可商购的三氟甲磺酸铁（II）。
• [EN] DIAROMATIC SUBSTITUTED ANTI-AIDS COMPOUNDS
  申请人：THE UPJOHN COMPANY

  公开号：WO1991009849A1

  公开（公告）日：1991-07-11

  (EN) The present invention includes diaromatic substituted heterocyclic compounds (III) which are useful in treating individuals infected with the HIV virus. The invention includes certain previously generically disclosed anti-AIDS piperazinyl compounds (IV) and a method of treating HIV infected individuals with the indoles of formula (V) and the anti-AIDS amines (X).(FR) Composés hétérocyclique (III) diaromatique substitué, utiles dans le traitement d'individus contaminés par le virus VIH. L'invention comprend certains composés (IV) de pipérazinyle anti-SIDA antérieurement décrits, ainsi qu'un procédé de traitement d'individus contaminés par VIH, à l'aide d'indoles de la formule (V) et à l'aide des amines (X) anti-SIDA.

  (中文) 本发明涉及二芳基取代杂环化合物(III)，其在治疗感染HIV病毒的个体中具有用途。该发明包括先前通用抗艾滋病的哌嗪化合物(IV)，以及使用公式(V)的吲哚和抗艾滋病胺(X)治疗HIV感染个体的方法。
• Intramolecular C−H Amination Reactions:  Exploitation of the Rh₂(II)-Catalyzed Decomposition of Azidoacrylates
  作者：Benjamin J. Stokes、Huijun Dong、Brooke E. Leslie、Ashley L. Pumphrey、Tom G. Driver

  DOI：10.1021/ja072219k

  日期：2007.6.1

  Rhodium(II) perfluorobutyrate-mediated decomposition of vinyl azides provides a new, mild entry into Rh-2(II) nitrenoid chemistry. This methodology allows rapid access to a variety of complex, functionalized N-heterocycles in two steps from commercially available starting materials.