dimethyl 7-bromoindole-2,3-dicarboxylate | 243836-46-6

• 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: dimethyl 7-bromoindole-2,3-dicarboxylate
• 英文别名: dimethyl 7-bromo-1H-indole-2,3-dicarboxylate
• CAS: 243836-46-6
• 化学式: C₁₂H₁₀BrNO₄
• 分子量: 312.12
• InChiKey: NTERCTCYBZQPLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 7-bromoindole-2,3-dicarboxylate 在 copper chromite 、 四(三苯基膦)钯 、 lithium hydroxide monohydrate 、 水 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 喹啉 、 丙酮 为溶剂， 反应 35.0h， 生成 pratosine
  参考文献：
  名称：

  Simple Synthesis of Pratosine and Hippadine by Intramolecular Palladium-Catalyzed Cyclization and Decarboxylation

  摘要：

  The palladium-catalyzed cyclization of dimethyl 1-(2-bromo-4,5-dimethoxybenzyl)indole-2,3-dicarboxylate in the presence of tetrakis(triphenylphosphine)palladium(0) and potassium acetate in hot 1,4-dioxane produced the 7H-pyrrolo[3,2,1-de]phenanthridine derivative, which was converted to pratosine by hydrolysis and decarboxylation. In a similar manner, hippadine was also prepared.

  DOI：

  10.3987/com-11-12167
• 作为产物：
  描述：

  1-(2-bromophenyl)-2-phenyldiazene 在 sodium hydroxide 、 锌 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 10.0h， 生成 dimethyl 7-bromoindole-2,3-dicarboxylate
  参考文献：
  名称：

  Synthesis and Reaction of Dimethyl 7-Bromoindole-2,3-dicarboxylates

  摘要：

  Reaction of 1-(4-benzyloxyphenyl)-2-phenylhydrazine with dimethyl acetylenedicarboxylate (DMAD) gave dimethyl 5-benzyloxyindole-2,3-dicarboxylate and dimethyl indole-2,3-dicarboxylate. However, treatment of 1-(2-bromophenyl)2-phenylhydrazine with DMAD afforded dimethyl 7-bromoindole-2,3-dicarboxylate, exclusively. In a similar manner, dimethyl 7-bromo-5-methoxyindole-2,3-dicarboxylate was also obtained from 1-(2-bromo-4-methoxyphenyl)-2phenylhydrazine. The bromo group of dimethyl 7-bromoindole-2,3-dicarboxylate was converted to an 1-ethoxyvinyl or vinyl group by treatment with tributyl-(1-ethoxyvinyl)tin or tributyl(vinyl)tin in the presence of a Pd(O) catalyst.

  DOI：

  10.3987/com-99-8543

文献信息

• [EN] SUBSTITUTED INDOLE MCL-1 INHIBITORS<br/>[FR] INHIBITEURS D'INDOLES MCL-1 SUBSTITUÉS
  申请人：UNIV VANDERBILT

  公开号：WO2017152076A1

  公开（公告）日：2017-09-08

  The present disclosure provides for compounds that inhibit the activity of an anti- apoptotic Bcl-2 family member Myeloid cell leukemia-1 (Mcl-1) protein. The present disclosure also provides for pharmaceutical compositions as well as methods for using compounds for treatment of diseases and conditions (e.g., cancer) characterized by the over- expression or dysregulation of Mcl-1 protein.

  本公开提供了抑制抗凋亡Bcl-2家族成员髓细胞白血病-1（Mcl-1）蛋白活性的化合物。本公开还提供了用于治疗由Mcl-1蛋白过度表达或失调所特征的疾病和病况（例如癌症）的药物组合物以及使用化合物的方法。
• SUBSTITUTED INDOLE MCL-1 INHIBITORS
  申请人：Vanderbilt University

  公开号：EP3423435A1

  公开（公告）日：2019-01-09
• Simple Synthesis of Pratosine and Hippadine by Intramolecular Palladium-Catalyzed Cyclization and Decarboxylation
  作者：Yasuyoshi Miki、Hideaki Umemoto、Masashi Dohshita、Hiromi Hamamoto

  DOI：10.3987/com-11-12167

  日期：——

  The palladium-catalyzed cyclization of dimethyl 1-(2-bromo-4,5-dimethoxybenzyl)indole-2,3-dicarboxylate in the presence of tetrakis(triphenylphosphine)palladium(0) and potassium acetate in hot 1,4-dioxane produced the 7H-pyrrolo[3,2,1-de]phenanthridine derivative, which was converted to pratosine by hydrolysis and decarboxylation. In a similar manner, hippadine was also prepared.
• Synthesis and Reaction of Dimethyl 7-Bromoindole-2,3-dicarboxylates
  作者：Yasuyoshi Miki、Ko-ichi Matsushita、Hajime Hibino、Hideaki Shirokoshi

  DOI：10.3987/com-99-8543

  日期：——

  Reaction of 1-(4-benzyloxyphenyl)-2-phenylhydrazine with dimethyl acetylenedicarboxylate (DMAD) gave dimethyl 5-benzyloxyindole-2,3-dicarboxylate and dimethyl indole-2,3-dicarboxylate. However, treatment of 1-(2-bromophenyl)2-phenylhydrazine with DMAD afforded dimethyl 7-bromoindole-2,3-dicarboxylate, exclusively. In a similar manner, dimethyl 7-bromo-5-methoxyindole-2,3-dicarboxylate was also obtained from 1-(2-bromo-4-methoxyphenyl)-2phenylhydrazine. The bromo group of dimethyl 7-bromoindole-2,3-dicarboxylate was converted to an 1-ethoxyvinyl or vinyl group by treatment with tributyl-(1-ethoxyvinyl)tin or tributyl(vinyl)tin in the presence of a Pd(O) catalyst.