5-iodo-2-(4-methoxyphenyl)-1H-indole | 1239440-14-2

• 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: 5-iodo-2-(4-methoxyphenyl)-1H-indole
• CAS: 1239440-14-2
• 化学式: C₁₅H₁₂INO
• 分子量: 349.171
• InChiKey: IOOLTPQPDKMPQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 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：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-iodo-2-(4-methoxyphenyl)-1H-indole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以19.5%的产率得到4-(5-iodo-1H-indol-2-yl)phenol
  参考文献：
  名称：

  Synthesis and characterization of novel phenylindoles as potential probes for imaging of β-amyloid plaques in the brain

  摘要：

  We synthesized a novel series of phenylindole (PI) derivatives and evaluated their biological activities as probes for imaging A beta plaques in vivo. The affinity for A beta plaques was assessed by an in vitro-binding assay using pre-formed synthetic A beta aggregates. 2-Phenyl-1H-indole (2-PI) derivatives showed high affinity for A beta 42 aggregates with K-i values ranging from 4 to 32 nM. 2-PI derivatives clearly stained A beta plaques in an animal model of AD. In biodistribution experiments using normal mice, 2-PI derivatives displayed sufficient uptake for imaging, ranging from 1.1% to 2.6% ID/g. Although additional modifications are necessary to improve uptake by and clearance from the brain, 2-PI derivatives may be useful as a backbone structure to develop novel Ab imaging agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.013
• 作为产物：
  描述：

  5-溴-2-(4-甲氧基苯基)-1H-吲哚 在 四(三苯基膦)钯 、 六甲基二锡 、 碘 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 3.5h， 以15 mg的产率得到5-iodo-2-(4-methoxyphenyl)-1H-indole
  参考文献：
  名称：

  Synthesis and characterization of novel phenylindoles as potential probes for imaging of β-amyloid plaques in the brain

  摘要：

  We synthesized a novel series of phenylindole (PI) derivatives and evaluated their biological activities as probes for imaging A beta plaques in vivo. The affinity for A beta plaques was assessed by an in vitro-binding assay using pre-formed synthetic A beta aggregates. 2-Phenyl-1H-indole (2-PI) derivatives showed high affinity for A beta 42 aggregates with K-i values ranging from 4 to 32 nM. 2-PI derivatives clearly stained A beta plaques in an animal model of AD. In biodistribution experiments using normal mice, 2-PI derivatives displayed sufficient uptake for imaging, ranging from 1.1% to 2.6% ID/g. Although additional modifications are necessary to improve uptake by and clearance from the brain, 2-PI derivatives may be useful as a backbone structure to develop novel Ab imaging agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.013

文献信息

• The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons
  作者：Shuling Yu、Linjun Qi、Kun Hu、Julin Gong、Tianxing Cheng、Qingzong Wang、Jiuxi Chen、Huayue Wu

  DOI：10.1021/acs.joc.7b00148

  日期：2017.4.7

  A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations

  首次开发了钯催化的2-（2-氨基芳基）乙腈与芳基硼酸的串联串联加成/环化反应，实现了直接构建吲哚骨架的新策略。该系统显示出良好的官能团耐受性和出色的化学选择性。特别地，卤素（例如，溴和碘）取代基适合于进一步的合成精细化，从而扩大了产物的多样性。初步的机械实验表明，这种转化涉及相继的亲核加成，然后进行分子内环化。