1,1-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 6678-85-9

• 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: 1,1-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 1,1-dimethyl-1,2,3,4-tetrahydro-β-carboline；1,1-dimethyl-2,3,4,9-tetrahydro-1H-β-carboline；2,3,4,9-Tetrahydro-1,1-dimethyl-1H-pyrido<3,4-b>indol；1,1-Dimethyl-1,2,3,4-tetrahydro-β-carbolin；1,1-Dimethyl-2,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 6678-85-9
• 化学式: C₁₃H₁₆N₂
• mdl: MFCD22058683
• 分子量: 200.283
• InChiKey: WZVZLIGRQSJGAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  352.5±32.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.384
• 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：

  1,1-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 25.33h， 生成 3,3-dimethyl-5,6-dihydro-7H-1,4-methanobenzo[e][1,4]diazonine-2,7(3H)-dione
  参考文献：
  名称：

  通过四氢-β-咔啉的Witkop氧化得到三环咪唑烷-4-酮。

  摘要：

  1-取代的1,1-二取代的四氢-β-咔啉在甲醛和其他醛的存在下经历高碘酸钠的氧化环膨胀，从而形成5,6-二氢-7H-1,4-甲基苯并[e] [1,4] ] diazonine-2,7（3H）-二酮，收率30-81％。在大多数情况下，形成这种新的6/8 / 5-三环系统的反应具有很高的非对映选择性。这些苯环中环酮基咪唑啉丁-4-酮扩展了四氢-β-咔啉氧化产物的范围。

  DOI：

  10.1021/acs.joc.9b03402
• 作为产物：
  描述：

  2-formyl-1,1-dimethyl-1,2,3,4-tetrahydro-β-carboline 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以96%的产率得到1,1-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  A Facile Synthesis of 1,1-Disubstituted 1,2,3,4-Tetrahydro-b-carbolines via Trifluoroacetic Acid Catalyzed Pictet- Spengler Reaction Using Titanium(IV) Isopropoxide as an Imination Reagent

  摘要：

  A synthesis of 1,1-disubstitued 1,2,3,4-tetrahydro-beta-carbolines (13) was achieved in a highly effective manner via the trifluoroacetic acid catalyzed Pictet-Spengler reaction of the keto imines (9) prepared from tryptamine (8) with acyclic and cyclic ketones using titanium(IV) isopropoxide as the imination reagent under one pot procedure. This reaction provides a convenient and general method for preparing various 1,2,3,4-tetrahydro-beta-carbolines derivatives.

  DOI：

  10.3987/com-02-s79

文献信息

• Two‐in‐One Strategy for Palladium‐Catalyzed C−H Functionalization in Water
  作者：Huiying Zeng、Zemin Wang、Chao‐Jun Li

  DOI：10.1002/anie.201813391

  日期：2019.2.25

  Transition metal catalyzed C−H functionalizations have been developed as powerful methods for C−C bond formations. Directing groups, removable directing groups, traceless directing groups, and transient directing groups (TDGs) have been successfully used to improve the reaction efficiencies. For the development of greener and more sustainable methods, C−H functionalization using a TDG that also serves

  过渡金属催化的CH官能化已被开发为形成CC键的有力方法。导向基团，可移动的导向基团，无痕导向基团和瞬态导向基团（TDG）已被成功地用于提高反应效率。为了开发更绿色，更可持续的方法，研究了使用TDG的CH功能化，该TDG还可以用作水性溶剂中的试剂。使用酮在水中的钯催化的色胺类胺的CH-H官能化成功生成了四氢-β-咔啉，其四级碳中心位于C1。讨论了氘标记实验以提供对该机理的深入了解。吡啶的C2位也通过该策略成功地官能化。
• SYNTHESIS OF NATURALLY OCCURING ECTEINASCIDINS AND RELATED COMPOUNDS
  申请人：Barrasa Valentin Martinez

  公开号：US20090163507A1

  公开（公告）日：2009-06-25

  Ecteinascidin compounds with a quinone ring for ring E are active as anti-cancer agents. Related processes and compounds are provided.

  Ecteinascidin化合物具有一个醌环的E环，可作为抗癌剂活性。提供了相关的过程和化合物。
• Indole C5‐Selective Bromination of Indolo[2,3‐a]quinolizidine Alkaloids via In Situ‐Generated Indoline Intermediate
  作者：Go Yoshimura、Jukiya Sakamoto、Mariko Kitajima、Hayato Ishikawa

  DOI：10.1002/chem.202401153

  日期：2024.6.20

  The indole C5-selective bromination of indolo[2,3-a]quinolizidine alkaloids by adding nearly equimolar amounts of Br3 ⋅ PyH and HCl in MeOH is disclosed. The resulting reaction plausibly proceeds through an indoline intermediate by the nucleophilic addition of MeOH to the C3-brominated indolenine intermediate. These simple, mild, and metal-free conditions are suitable for late-stage chemical conversions

  公开了通过在MeOH中添加几乎等摩尔量的Br 3 ·PyH和HCl来对吲哚并[2,3- a ]喹啉西啶生物碱进行吲哚C5选择性溴化。通过将MeOH亲核加成至C3-溴化吲哚啉中间体，所得反应似乎通过二氢吲哚中间体进行。这些简单、温和且不含金属的条件适用于全合成和药物化学中的后期化学转化。
• The synthesis of 1,1-disubstituted tetrahydro-β-carbolines induced by iodine
  作者：Y. Lingam、D. Muralimohan Rao、Dipal R. Bhowmik、Pachore Sharad Santu、K. Raghavendra Rao、Aminul Islam

  DOI：10.1016/j.tetlet.2007.06.099

  日期：2007.10

  A mild access to 1,1-disubstituted tetrahydro-beta-carbolines is described. Tryptamine is subjected to Pictet-Spengler cyclization with various ketones using iodine. (C) 2007 Elsevier Ltd. All rights reserved.
• Application of chlorotrimethylsilane in Pictet–Spengler reaction
  作者：Sergey V. Ryabukhin、Dmitriy M. Panov、Andrey S. Plaskon、Andrey A. Tolmachev、Radomyr V. Smaliy

  DOI：10.1007/s00706-012-0804-7

  日期：2012.11

  Chlorotrimethylsilane has been found to be an efficient condensing agent in the Pictet-Spengler reaction, affording an extremely straightforward synthetic route to tetrahydro-beta-carboline derivatives and their analogs. The applicability of the method has been studied, and a representative library of structurally diverse products has been created..