methyl-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate | 82789-35-3

• 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: methyl-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate
• 英文别名: 1-(3,4-Methylenedioxyphenyl)-1,2,3,4-tetrahydro-3-carbomethoxy-β-carboline；Methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate；methyl 1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylate；methyl 1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 82789-35-3
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: LIPVUDSNGRJSQE-UHFFFAOYSA-N

物化性质

• 沸点：
  531.0±50.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate 以91的产率得到(1S,3R)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride
  参考文献：
  名称：

  Tetrahedron: Asymmetry 2009, 20, 2090-2096

  摘要：

  DOI：
• 作为产物：
  描述：

  以98的产率得到methyl-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate
  参考文献：
  名称：

  Tetrahedron: Asymmetry 2009, 20, 2090-2096

  摘要：

  DOI：

文献信息

• Efficient and Practical One-Pot Conversions of N-Tosyltetrahydroisoquinolines into Isoquinolines and of N-Tosyltetrahydro-β-carbolines into β-Carbolines through Tandem β-Elimination and Aromatization
  作者：Jing Dong、Xiao-Xin Shi、Jing-Jing Yan、Jing Xing、Qiang Zhang、Sen Xiao

  DOI：10.1002/ejoc.201001153

  日期：2010.12

  An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) into β-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-β-carbolines as intermediates, and these were then oxidized in situ by

  描述了一种将 N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) 转化为异喹啉和将 N-tosyltetrahydro-β-carbolines (N-tosyl-THBCs) 转化为 β-咔啉的有效、实用和通用的方法。在二甲基亚砜中用碱处理 N-tosyl-THIQs 或 N-tosyl-THBCs 得到作为中间体的二氢异喹啉或二氢-β-咔啉，然后这些被分子氧原位氧化得到异喹啉或 β-咔啉。产量。两种一锅法转化都是通过串联β-消除和芳构化发生的。
• Convenient synthesis of 1-aryl-9H-β-carboline-3-carbaldehydes and their transformation into dihydropyrimidinone derivatives by Biginelli reaction
  作者：Péter Ábrányi-Balogh、András Dancsó、Dávid Frigyes、Balázs Volk、György Keglevich、Mátyás Milen

  DOI：10.1016/j.tet.2014.06.073

  日期：2014.9

  In the present work, a practical synthesis of 1-aryl-β-carboline-3-carbaldehydes as versatile building blocks and their application in Biginelli reaction is reported. The starting material of the four-step synthesis is racemic tryptophan methyl ester. The procedure involves a Pictet–Spengler cyclization, a dehydrogenation, an ester reduction, and an alcohol oxidation step. The β-carboline-3-carbaldehydes

  在目前的工作中，报道了一种实用的1-芳基-β-咔啉-3-甲醛的合成方法，作为通用的结构单元及其在Biginelli反应中的应用。四步合成的起始原料是外消旋色氨酸甲酯。该过程涉及Pictet-Spengler环化，脱氢，酯还原和醇氧化步骤。使用Biginelli反应，将β-咔啉-3-甲醛进一步转化为在位置3上具有药理学意义的二氢嘧啶环的衍生物。
• Manufacturing process for Tadalafil from racemic or L-tryptophan
  申请人：Soukup Milan

  公开号：US20120123124A1

  公开（公告）日：2012-05-17

  The present invention relates to a novel manufacturing process of pharmaceutically active compound of formula I, having (6R,12aR)-configuration, used for treatment of erectile dysfunction. Starting from racemic or L-tryptophan the invention describes preparation of an enantiomerically pure intermediate of formula II which is a known precursor in the synthesis of Tadalafil (formula I).

  本发明涉及一种用于治疗勃起功能障碍的具有（6R，12aR）-构型的化学药物活性化合物I的新型制造过程。从外消旋或L-色氨酸出发，本发明描述了一种制备公式II的对映纯中间体的方法，该中间体是犀利士（化合物I）合成中已知的前体。
• [EN] MODIFIED PICTET-SPENGLER REACTION AND PRODUCTS PREPARED THEREFROM<br/>[FR] REACTION DE PICTET-SPENGLER MODIFIEE ET PRODUITS PREPARES A PARTIR DE CETTE DERNIERE
  申请人：LILLY ICOS LLC

  公开号：WO2004011463A1

  公开（公告）日：2004-02-05

  A method of introducing a second stereogenic center into a tetrahydro-ß-carboline have two stereogenic centers using a modified Pictet-Spengler reaction is disclosed. The method provides a desired cis- or trans-isomer in high yield and purity, and in short processes times.

  一种在四氢-ß-咔啉中引入第二个立体异构中心的方法，利用改良的Pictet-Spengler反应进行。该方法以高产率和纯度提供所需的顺式或反式异构体，并在短时间内完成。
• [EN] PROCESS FOR THE PREPARATION OF 2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLIN-3-CARBOXYLIC ACID ESTERS"<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ESTERS DE L'ACIDE 2,3,4,9-TÉTRAHYDRO-1H-BÊTA-CARBOLIN-3-CARBOXYLIQUE
  申请人：ENDURA SPA

  公开号：WO2009103787A1

  公开（公告）日：2009-08-27

  The present invention relates to the process of preparation of 2,3,4,9-tetrahydro- 1 /-/-β-carbolin-3-carboxylic acid esters substituted in position 1 of the general formula (I). in the preferred diastereoisomeric form through a single step starting from tryptophan in racemic form and/or its enantiomers and from 3,4-(methylenedioxy)benzaldehyde.

  本发明涉及一种从色氨酸的外消旋形式和/或其对映体以及3,4-(亚甲二氧基)苯甲醛出发，通过单步法制备1位取代的2,3,4,9-四氢-1H-β-吲哚-3-羧酸酯的过程，其一种首选的对映异构形式。