benzyl 1-benzyl-1H-indole-6-carboxylate | 338959-28-7

• 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: benzyl 1-benzyl-1H-indole-6-carboxylate
• 英文别名: benzyl (1-benzyl)indole-6-carboxylate；Benzyl (1-benzyl)indole-6carboxylate；benzyl 1-benzylindole-6-carboxylate
• CAS: 338959-28-7
• 化学式: C₂₃H₁₉NO₂
• 分子量: 341.409
• InChiKey: VXJQZHMPCJTSQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl 1-benzyl-1H-indole-6-carboxylate 在 sodium hydroxide 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-benzylindoline-6-carboxylic acid
  参考文献：
  名称：

  8-Piperazinyl-2,3-dihydropyrrolo[3,2-g]isoquinolines: Potent, selective, orally bioavailable 5-HT1 receptor ligands

  摘要：

  The novel 8-piperazinyl-2,3-dihydropyrroloisoquinoline template was synthesized in nine steps. The template was N-substituted to give a series of compounds showing binding to human cloned 5-HT1A, 5-HT1B and 5-HT1D receptors with pK(i)'s greater than 9 and selectivities up to 1000-fold against other serotonin, dopamine and adrenergic receptors. Several compounds were shown to possess weak partial agonist activity in cloned receptors, which translated to antagonism in in vitro studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.042
• 作为产物：
  描述：

  6-吲哚甲酸 、 溴甲苯 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 16.5h， 以90%的产率得到benzyl 1-benzyl-1H-indole-6-carboxylate
  参考文献：
  名称：

  ISOQUINOLINE AND QUINAZOLINE DEIVATIVES HAVING A COMBINED 5HT1A, 5HT1B AND 5HT1D RECEPTOR ACTIVITY

  摘要：

  公开号：

  EP1228043B1

文献信息

• Pd-Catalyzed Direct and Selective CH Functionalization: C3-Acetoxylation of Indoles
  作者：Qiang Liu、Gang Li、Hong Yi、Pan Wu、Jie Liu、Aiwen Lei

  DOI：10.1002/chem.201002547

  日期：2011.2.18

  one! A novel Pd‐catalyzed direct and selective C3‐acetoxylation of indole derivatives has been accomplished (see scheme). This selective CH activation reaction was implemented without the assistance of directing groups and took place under mild conditions. The kinetic study revealed that the reaction was zero‐order with respect to the oxidant and first‐order with respect to the indole derivatives.

  被选中的人或事物！已经完成了新颖的钯催化吲哚衍生物的直接和选择性C3-乙酰氧基化反应（参见方案）。这种选择性Ç  ħ活化反应没有定位基团的协助下实现，并且在温和的条件下发生的。动力学研究表明，相对于氧化剂，反应是零级的；对于吲哚衍生物，反应是一级的。
• Palladium-Catalyzed Regioselective Aerobic Oxidative CH/NH Carbonylation of Heteroarenes under Base-Free Conditions
  作者：Hua Zhang、Dong Liu、Caiyou Chen、Chao Liu、Aiwen Lei

  DOI：10.1002/chem.201101300

  日期：2011.8.22

  balloon pressure of CO, the direct oxidative carbonylation of various heteroarenes with different alcohols was achieved in good to high yields with air as the oxidant in the presence of PdCl2(PPh3)2 (see scheme). Notably, this transformation was carried out under base‐free conditions. The reaction showed remarkably high regioselectivity and presents an environmentally benign protocol for the synthesis

  清除空气！通过使用CO的球囊压力，在存在PdCl 2（PPh 3）2的情况下，以空气作为氧化剂，可以以高至高产率实现各种杂芳烃与不同醇的直接氧化羰基化反应（参见方案）。值得注意的是，这种转化是在无碱条件下进行的。该反应显示出极高的区域选择性，并为羧酸衍生物的合成提供了环境友好的方案。
• Isoquinoline and quinazoline derivatives having a combined 5HT1A, 5HT1B, and 5HT1D receptor activity
  申请人：Gaster Mary Laramie

  公开号：US20050239797A1

  公开（公告）日：2005-10-27

  The invention relates to novel isoquinoline and quinazoline derivatives having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of various disorders.

  本发明涉及具有药理活性的新异喹啉和喹唑啉衍生物，其制备方法，含有它们的组合物以及它们在治疗各种疾病中的应用。
• NOVEL FUSED PYROLE DERIVATIVE
  申请人：Sone Toshihiko

  公开号：US20100190768A1

  公开（公告）日：2010-07-29

  The present invention relates to a compound represented by the formula (1) which is useful as a glucocorticoid receptor function regulating agent, an anti-inflammatory agent or an antidiabetic agent, or a pharmaceutically acceptable salt thereof: wherein R 1 is aralkyl, etc.; R 2 is H, etc.; —W 4 ═W 5 —W 6 ═W 7 — is a group of the formula: —CR 4 ═CR 5 —CR 6 ═CR 7 — (in which R 4 , R 5 , R 6 and R 7 are independently a group of the formula: -E-A (E is a single bond, etc., A is H or nitro, etc.)), etc.; R 8 is a group of the formula: —OR 11 (R 11 is H, etc.), etc.; R 9 is trifluoromethyl, etc.; R 10 is a group of the formula: —[C(R 13 )(R 14 )] n —R 15 (R 13 and R 14 are independently H, etc., n is an integer of 0 to 10, R 15 is a group of the formula: N(R 18 )R 19 (R 18 and R 19 form a nitrogen-containing heteromonocycle together with a nitrogen atom to which they are bonded), etc.).

  本发明涉及一种化合物，其化学式为(1)，它可作为糖皮质激素受体功能调节剂、抗炎剂或抗糖尿病剂，或其药学上可接受的盐使用：其中R1为芳基烷基等；R2为H等；-W4═W5-W6═W7-为以下式的基团：-CR4═CR5-CR6═CR7-(其中R4、R5、R6和R7独立地为以下式的基团：-E-A(E为单键等，A为H或硝基等))等；R8为以下式的基团：-OR11(R11为H等)等；R9为三氟甲基等；R10为以下式的基团：-[C(R13)(R14)]n-R15(R13和R14独立地为H等，n为0到10的整数，R15为以下式的基团：N(R18)R19(R18和R19与它们连接的氮原子一起形成含氮杂单环)等。
• NOVEL FUSED PYRROLE DERIVATIVE
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1930320A1

  公开（公告）日：2008-06-11

  The present invention relates to a compound represented by the formula (1) which is useful as a glucocorticoid receptor function regulating agent, an anti-inflammatory agent or an antidiabetic agent, or a pharmaceutically acceptable salt thereof: wherein R1 is aralkyl, etc.; R2 is H, etc.; -W4=W5-W6=W7- is a group of the formula: -CR4=CR5-CR6=CR7- (in which R4, R5, R6 and R7 are independently a group of the formula: -E-A (E is a single bond, etc., A is H or nitro, etc.)), etc.; R8 is a group of the formula: -OR11 (R11 is H, etc.), etc.; R9 is trifluoromethyl, etc.; R10 is a group of the formula: -[C(R13)(R14)]n-R15 (R13 and R14 are independently H, etc., n is an integer of 0 to 10, R15 is a group of the formula: N(R18)R19 (R18 and R19 form a nitrogen-containing heteromonocycle together with a nitrogen atom to which they are bonded), etc.).

  本发明涉及一种由式（1）表示的化合物，它可用作糖皮质激素受体功能调节剂、抗炎剂或抗糖尿病剂，或其药学上可接受的盐： 其中 R1 是芳烷基等；R2 是 H 等；-W4=W5-W6=W7- 是式中的基团：-CR4=CR5-CR6=CR7-（其中 R4、R5、R6 和 R7 独立地是式子中的一个基团：-E-A（E 是单键等，A 是 H 或硝基等））等； R8 是式中的基团：-OR11（R11 是 H 等）等； R9 是三氟甲基等； R10 是式中的基团：-[C(R13)(R14)]n-R15（R13 和 R14 独立地为 H 等，n 为 0 至 10 的整数，R15 为式中的基团：N(R18)R19（R18 和 R19 与它们键合的氮原子一起形成含氮杂单环）等）。