2-(3-iodophenyl)-1H-indole | 914389-67-6

• 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: 2-(3-iodophenyl)-1H-indole
• CAS: 914389-67-6
• 化学式: C₁₄H₁₀IN
• 分子量: 319.145
• InChiKey: JOLCQKZDYKFSEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(3-iodophenyl)-1H-indole 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-benzyl-2-(2-(3-iodophenyl)-1H-indol-3-yl)-2-oxoacetamide
  参考文献：
  名称：

  Synthesis and receptor binding studies of halogenated N,N-dialkylel-(2-phenyl-1H-indol-3-yl)glyoxylamides to visualize peripheral benzodiazepine receptors with SPECT or PET

  摘要：

  A library of halogenated 2-arylindolyl-3-oxocarboxamides was prepared to develop radioligands to visualize cerebral PBR by SPECT and PET imaging. In vitro evaluation showed that most of the synthesized compounds were selective,high-affinity PBR ligands with adequate lipophilicity (log D(7.4) in the range of 1.6-2.4). The iodinated derivative 11 (K(i) = 2.6 nM) and the fluorinated analog 26 (K(i) = 6.2 nM) displayed higher affinity than reference compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.001
• 作为产物：
  描述：

  1-[1-(3-溴苯基)亚乙基]-2-苯基肼 在 copper(l) iodide 、 PPA 、 四甲基乙二胺 、 sodium iodide 作用下， 以 1,4-二氧六环 、 xylene 为溶剂， 反应 20.33h， 生成 2-(3-iodophenyl)-1H-indole
  参考文献：
  名称：

  Synthesis and receptor binding studies of halogenated N,N-dialkylel-(2-phenyl-1H-indol-3-yl)glyoxylamides to visualize peripheral benzodiazepine receptors with SPECT or PET

  摘要：

  A library of halogenated 2-arylindolyl-3-oxocarboxamides was prepared to develop radioligands to visualize cerebral PBR by SPECT and PET imaging. In vitro evaluation showed that most of the synthesized compounds were selective,high-affinity PBR ligands with adequate lipophilicity (log D(7.4) in the range of 1.6-2.4). The iodinated derivative 11 (K(i) = 2.6 nM) and the fluorinated analog 26 (K(i) = 6.2 nM) displayed higher affinity than reference compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.001

文献信息

• Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
  作者：Kai Yang、Yixian Lou、Chenglan Wang、Liang‐Wen Qi、Tongchang Fang、Feng Zhang、Hetao Xu、Lu Zhou、Wangyang Li、Guan Zhang、Peiyuan Yu、Qiuling Song

  DOI：10.1002/anie.201913656

  日期：2020.2.17

  A new chiral Brønsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This "designer acid catalyst", which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities

  由手性磷酸硼（CPAB）配合物和水原位生成的新手性布朗斯台德酸已成功地用于不对称吲哚还原。如DFT计算所建议的，这种“设计酸催化剂”比TsOH酸性更强，可实现C2-芳基取代的N-未保护的吲哚空前的直接不对称还原，并具有良好的对映选择性，并具有宽泛的官能团耐受性。DFT计算和机理实验表明该反应经历了C3质子化和氢化物转移过程。此外，庞大的C 2-烷基取代的N-未保护的吲哚也适用于该体系。