9-allyl-4,9-dihydro-3H-β-carboline | 868846-71-3

• 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: 9-allyl-4,9-dihydro-3H-β-carboline
• 英文别名: 9-Prop-2-enyl-3,4-dihydropyrido[3,4-b]indole；9-prop-2-enyl-3,4-dihydropyrido[3,4-b]indole
• CAS: 868846-71-3
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: ARGOXMPCKXYDAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-allyl-4,9-dihydro-3H-β-carboline 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 9-allyl-1-ethynyl-2-(tolylsulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Enyne and dienyne metathesis reactions in β-carbolines

  摘要：

  New indolic enynes and dienynes, based on the P-carboline system, give metathesis products with ruthenium catalysts. The synthesis of the starting materials is readily achieved from tryptamine. The tuning up of the conditions for the metathesis is discussed. Cascade metathesis gives an oxidized pentacyclic product. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.140
• 作为产物：
  描述：

  N-[2-(1H-吲哚-3-基)乙基]甲酰胺 在 sodium hydroxide 、 四丁基溴化铵 、 三氯氧磷 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 1.0h， 生成 9-allyl-4,9-dihydro-3H-β-carboline
  参考文献：
  名称：

  N（9）-（ω-硝基烷基）-3,4-二氢-β-咔啉的分子内曼尼希型氨基和酰胺烷基化反应生成的1,2,3,4-四氢-β-咔啉

  摘要：

  将2- [1-（ω-硝基烷基）-1 H-吲哚-3-基]乙基甲酰胺11转化为相应的9-（ω-硝基烷基）-4,9-二氢-3 H -β-咔啉5并通过高产率地将非对映选择性分子内氨基烷基化成环状的四氢-β-咔啉13。化合物5的分子内N-酰基环化得到具有中等选择性的两种非对映异构形式18和19的四环二氮杂环烷[ jk ]芴。对化合物18和19进行的共轭加成反应导致五环吲哚并[3,2,1- de ]吡啶并[3,2,1- jk ]萘并吡啶酮26a或二氮杂苯并[ a ]萘并[2,1,8- cde ] azulenone 26b。

  DOI：

  10.1016/j.tet.2006.08.020

文献信息

• Catalytic asymmetric synthesis of 1,1-disubstituted tetrahydro-β-carbolines by phase-transfer catalyzed alkylations
  作者：Seiji Shirakawa、Kun Liu、Hironobu Ito、Keiji Maruoka

  DOI：10.1039/c0cc04447d

  日期：——

  Efficient catalytic asymmetric synthesis of 1,1-disubstituted tetrahydro-beta-carbolines has been achieved via asymmetric alkylation of 1-cyanotetrahydro-beta-carbolines using a binaphthyl-modified N-spiro-type chiral phase-transfer catalyst. This is a valuable example of hitherto difficult highly enantioselective alkylations at alpha-carbon of the cyano group under phase-transfer conditions.

  通过使用双萘基修饰的N-螺环型手性相转移催化剂对1-氰基四氢-β-咔啉进行不对称烷基化，已经实现了1,1-二取代的四氢-β-咔啉的高效催化不对称合成。这是迄今为止在相转移条件下氰基的α-碳上难以进行的高度对映选择性烷基化的有价值的实例。
• Novel chemistry of β-carbolines. Expedient synthesis of polycyclic scaffolds
  作者：Álvaro González-Gómez、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1016/j.tet.2009.02.051

  日期：2009.4

  Functionalization of beta-carbolines is a challenge as numerous natural alkaloids with different biological activities present this heterocycle. The RCM is used herein with allyl-, vinyl-, ethynyl-, and propargyl-beta-carbolines to generate additionally fused hetero- and carbocycles, and it is combined with other cyclization processes to achieve great molecular complexity in one synthetic step. Thus, an RCM-Diels-Alder sequence gives pentacyclic Compounds related with certain alkaloids. On the other hand, vinyl-pyrrolo[2,1-a]-beta-carbolines and vinyl-beta-carbolines give different products upon reaction with activated dienophiles. Thus, a novel domino processes affords complex polycycles like 35-38. Other alkynes like 3-butyn-2-one give a Stevens rearrangement. (C) 2009 Elsevier Ltd. All rights reserved.
• Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (±)-debromoarborescidine B
  作者：Gordana Tasic、Milena Simic、Stanimir Popovic、Suren Husinec、Veselin Maslak、Vladimir Savic

  DOI：10.1016/j.tetlet.2013.06.069

  日期：2013.8

  Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B. (C) 2013 Elsevier Ltd. All rights reserved.