1-(2-iodo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline | 303744-04-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(2-iodo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 1-(2-iodophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 303744-04-9
• 化学式: C₁₇H₁₅IN₂
• 分子量: 374.224
• InChiKey: SJAIEKVSGDONJD-UHFFFAOYSA-N

物化性质

• 沸点：
  483.7±45.0 °C(Predicted)
• 密度：
  1.620±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  丙二烯 、 1-(2-iodo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline 在 palladium diacetate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.32 kPa 条件下， 反应 16.0h， 以90%的产率得到15-Methylidene-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16,18,20-heptaene
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1
• 作为产物：
  描述：

  [2-(1H-indol-3-yl)ethyl]-(2-iodo-benzylidene)-amine 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以81%的产率得到1-(2-iodo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1

文献信息

• Rapid, Label‐Free Screening of Diverse Biotransformations by Flow‐Injection Mass Spectrometry
  作者：Sarah A. Berger、Christopher Grimm、Jonathan Nyenhuis、Stefan E. Payer、Isabel Oroz‐Guinea、Joerg H. Schrittwieser、Wolfgang Kroutil

  DOI：10.1002/cbic.202300170

  日期：2023.6

  Mass spectrometry‐based high‐throughput screening methods combine the advantages of photometric or fluorometric assays and analytical chromatography, as they are reasonably fast (throughput ≥1 sample/min) and broadly applicable, with no need for labelled substrates or products. However, the established MS‐based screening approaches require specialised and expensive hardware, which limits their broad use throughout the research community. We show that a more common instrumental platform, a single‐quadrupole HPLC‐MS, can be used to rapidly analyse diverse biotransformations by flow‐injection mass spectrometry (FIA‐MS), that is, by automated infusion of samples to the ESI‐MS detector without prior chromatographic separation. Common organic buffers can be employed as internal standard for quantification, and the method provides readily validated activity and selectivity information with an analytical run time of one minute per sample. We report four application examples that cover a broad range of analyte structures and concentrations (0.1–50 mM before dilution) and diverse biocatalyst preparations (crude cell lysates and whole microbial cells). Our results establish FIA‐MS as a versatile and reliable alternative to more traditional methods for screening enzymatic reactions.

  摘要 基于质谱的高通量筛选方法结合了光度或荧光测定法和分析色谱法的优点，因为它们速度快（通量≥1 样品/分钟），适用范围广，无需标记底物或产物。然而，现有的基于质谱的筛选方法需要专业而昂贵的硬件，这限制了它们在整个研究界的广泛应用。我们的研究表明，单四极杆高效液相色谱-质谱（HPLC-MS）这一更常见的仪器平台可用于通过流动注射质谱（FIA-MS）快速分析各种生物转化，即通过自动将样品注入 ESI-MS 检测器，而无需事先进行色谱分离。常用的有机缓冲液可用作定量的内标，该方法可提供易于验证的活性和选择性信息，每个样品的分析运行时间仅为一分钟。我们报告了四个应用实例，涵盖了广泛的分析物结构和浓度（稀释前为 0.1-50 mM）以及不同的生物催化剂制备方法（粗细胞裂解物和整个微生物细胞）。我们的研究结果表明，FIA-MS 是筛选酶促反应的传统方法之外的一种多功能、可靠的替代方法。
• Silver- and Gold-Mediated Intramolecular Cyclization to Substituted Tetracyclic Isoquinolizinium Hexafluorostilbates
  作者：Fang Liu、Xiao Ding、Lei Zhang、Yu Zhou、Linxiang Zhao、Hualiang Jiang、Hong Liu

  DOI：10.1021/jo1006174

  日期：2010.9.3

  A convenient route for the synthesis of various charged tetracyclic isoquinolizinium hexafluorostilbates was developed using AgSbF6/AuCl(PPh3) for the intramolecular addition of amine to alkyne. The described process is tolerant of a variety of functional groups and broadens the diversity of substrates with the use of 8-substituted tetracyclic isoquinolizinium salts.
• Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes
  作者：Ronald Grigg、William S MacLachlan、David T MacPherson、Visuvanathar Sridharan、Selvaratnam Suganthan、Mark Thornton-Pett、Jin Zhang

  DOI：10.1016/s0040-4020(00)00628-1

  日期：2000.8

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.