3-(5-iodo-1H-indol-3-yl)-propanol | 1045805-53-5

• 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: 3-(5-iodo-1H-indol-3-yl)-propanol
• 英文别名: 3-(5-iodo-1H-indol-3-yl)propan-1-ol
• CAS: 1045805-53-5
• 化学式: C₁₁H₁₂INO
• 分子量: 301.127
• InChiKey: SMGJOYQUQOWDBC-UHFFFAOYSA-N

物化性质

• 沸点：
  449.8±30.0 °C(predicted)
• 密度：
  1.763±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(5-iodo-1H-indol-3-yl)-propanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到3-(3-bromo-propyl)-5-iodo-1H-indole
  参考文献：
  名称：

  Carbon-11 labeled indolylpropylamine analog as a new potential PET agent for imaging of the serotonin transporter

  摘要：

  The synthesis and structure-activity relationship of a new class of indole derivatives with low-nanomolar affinity for the SERT and high selectivity versus the 5-HT1A receptor were recently reported. Based on their chemical structure, four new indolylpropylamine derivatives which contain atoms to afford future labeling with PET isotopes, were synthesized and evaluated as SERT ligands. The chemistry of these novel derivatives, their biological evaluation, the general method of preparing the precursor indole for labeling, and the C-11 labeling of the most promising indole derivative, are described herein. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.006
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 4-碘苯肼 在 硫酸 作用下， 以 水 为溶剂， 反应 2.0h， 以36%的产率得到3-(5-iodo-1H-indol-3-yl)-propanol
  参考文献：
  名称：

  Carbon-11 labeled indolylpropylamine analog as a new potential PET agent for imaging of the serotonin transporter

  摘要：

  The synthesis and structure-activity relationship of a new class of indole derivatives with low-nanomolar affinity for the SERT and high selectivity versus the 5-HT1A receptor were recently reported. Based on their chemical structure, four new indolylpropylamine derivatives which contain atoms to afford future labeling with PET isotopes, were synthesized and evaluated as SERT ligands. The chemistry of these novel derivatives, their biological evaluation, the general method of preparing the precursor indole for labeling, and the C-11 labeling of the most promising indole derivative, are described herein. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.006

文献信息

• A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents
  作者：Xiaofeng Ma、Joshua J. Farndon、Tom A. Young、Natalie Fey、John F. Bower

  DOI：10.1002/anie.201708176

  日期：2017.11.13

  A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.

  概述了具有广泛范围的 CN 键形成脱芳构化方案。具体来说，双功能氨基试剂用于顺序亲核和亲电CN键形成，后者影响关键的脱芳构化步骤。使用这种方法，只需两到三个步骤即可将 γ-芳基化醇转化为各种差异保护的螺环吡咯烷。