1-acetyl-3,4-dihydro-β-carboline | 934463-33-9

• 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-acetyl-3,4-dihydro-β-carboline
• 英文别名: 1-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)ethanone
• CAS: 934463-33-9
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: TVHNOPLTPJMVCW-UHFFFAOYSA-N

物化性质

• 沸点：
  429.0±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetyl-3,4-dihydro-β-carboline 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以88%的产率得到1-(9H-beta-咔啉-1-基)乙酮
  参考文献：
  名称：

  通过 1-Benzyl-3,4-dihydro-β-Carbolines 串联苄基氧化和芳构化的高效一锅法全合成 Eudistomins Y1-Y7

  摘要：

  描述了eudistomin Y7 (7) 的首次全合成和eudistomin Y1–Y6 (1–6) 的全合成。1-苄基-3,4-二氢-β-咔啉（11）在室温下通过串联苄基氧化和芳构化的一锅法高效转化为1-苯甲酰基-β-咔啉（14）作为关键步骤还详细研究了这些全合成。

  DOI：

  10.1002/ejoc.201300080
• 作为产物：
  描述：

  N-lactoyltryptamine 在 conc. TFA 作用下， 反应 0.75h， 以0.9 mg的产率得到1-acetyl-3,4-dihydro-β-carboline
  参考文献：
  名称：

  The role of methylglyoxal in the non-enzymatic conversion of tryptophan, its methyl ester and tryptamine to 1-acetyl-β-carbolines

  摘要：

  Non-enzymatic modi. cation of L-tryptophan ( 1) and its metabolites and derivatives with aldehydes, via the Pictet-Spengler reaction, affords beta-carbolines. Here we demonstrate that methylglyoxal ( 2) generates 1-acetyl-beta-carbolines from tryptophan ( 1), from its methyl ester ( 6) and from tryptamine ( 4); however, 2 did not generate 1-(1-hydroxyethyl)-beta-carboline derivates. HPLC analysis of model reaction systems showed formation of 1-acetyl-beta-carboline ( 3) and 1-acetyl-beta-carboline-3-carboxylic acid ( 5) during incubation of 1 and 2, at pH 5.7 and 7.4, at 100 degrees C, and only 5 at 37 degrees C, at the same pH values, with limited access of oxygen. Aerobic conditions caused higher formation of 3 at 37 degrees C at both pH values, while, at higher temperature, the same effect was only observed at pH5.7. Lack of oxygen did not much influence the formation of 3 or 5 at both pH and temperature values, in comparison with the formation at limited access of oxygen. Incubation of 2 and 6 generated methyl-1-acetyl-beta-carboline-3-carboxylate ( 7) together with 3 and 5 as a result of hydrolysis of 6 into 1 and, partially, 7 into 5, while in incubation mixtures of 2 and 4 only unstable 1-acetyl-3,4-dihydro-beta-carboline ( 8) was observed. Incubation of 1 with D-glucose as well as incubation of tryptophan with Amadori product 18 under similar conditions did not generate carbolines 3 or 5. For the first time, we were able to demonstrate the presence of 1-acetyl-beta-carboline-3-carboxylic acid ( 5) in some commercially available ketchups and in previously heated tomato concentrate. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.039

文献信息

• The role of methylglyoxal in the non-enzymatic conversion of tryptophan, its methyl ester and tryptamine to 1-acetyl-β-carbolines
  作者：Ina Nemet、Lidija Varga-Defterdarović

  DOI：10.1016/j.bmc.2008.02.039

  日期：2008.4

  Non-enzymatic modi. cation of L-tryptophan ( 1) and its metabolites and derivatives with aldehydes, via the Pictet-Spengler reaction, affords beta-carbolines. Here we demonstrate that methylglyoxal ( 2) generates 1-acetyl-beta-carbolines from tryptophan ( 1), from its methyl ester ( 6) and from tryptamine ( 4); however, 2 did not generate 1-(1-hydroxyethyl)-beta-carboline derivates. HPLC analysis of model reaction systems showed formation of 1-acetyl-beta-carboline ( 3) and 1-acetyl-beta-carboline-3-carboxylic acid ( 5) during incubation of 1 and 2, at pH 5.7 and 7.4, at 100 degrees C, and only 5 at 37 degrees C, at the same pH values, with limited access of oxygen. Aerobic conditions caused higher formation of 3 at 37 degrees C at both pH values, while, at higher temperature, the same effect was only observed at pH5.7. Lack of oxygen did not much influence the formation of 3 or 5 at both pH and temperature values, in comparison with the formation at limited access of oxygen. Incubation of 2 and 6 generated methyl-1-acetyl-beta-carboline-3-carboxylate ( 7) together with 3 and 5 as a result of hydrolysis of 6 into 1 and, partially, 7 into 5, while in incubation mixtures of 2 and 4 only unstable 1-acetyl-3,4-dihydro-beta-carboline ( 8) was observed. Incubation of 1 with D-glucose as well as incubation of tryptophan with Amadori product 18 under similar conditions did not generate carbolines 3 or 5. For the first time, we were able to demonstrate the presence of 1-acetyl-beta-carboline-3-carboxylic acid ( 5) in some commercially available ketchups and in previously heated tomato concentrate. (c) 2008 Elsevier Ltd. All rights reserved.
• Total Syntheses of Eudistomins Y₁-Y₇by an Efficient One-Pot Process of Tandem Benzylic Oxidation and Aromatization of 1-Benzyl-3,4-dihydro-β-Carbolines
  作者：Tien Ha Trieu、Jing Dong、Qiang Zhang、Bo Zheng、Tian-Zhuo Meng、Xia Lu、Xiao-Xin Shi

  DOI：10.1002/ejoc.201300080

  日期：2013.6

  The first total synthesis of eudistomin Y7 (7) and total syntheses of eudistomins Y1–Y6 (1–6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail.

  描述了eudistomin Y7 (7) 的首次全合成和eudistomin Y1–Y6 (1–6) 的全合成。1-苄基-3,4-二氢-β-咔啉（11）在室温下通过串联苄基氧化和芳构化的一锅法高效转化为1-苯甲酰基-β-咔啉（14）作为关键步骤还详细研究了这些全合成。