methyl 1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 856968-24-6

• 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-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 856968-24-6
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: YHIDBQSPCIGAII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 碘 、 potassium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以98%的产率得到methyl 1-benzoyl-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Tandem iodine-mediated oxidations of tetrahydro-β-carbolines: total synthesis of eudistomins Y1–Y7

  摘要：

  报道了一种高效的碘介导的四氢-β-咔啉氧化反应，通过串联C-H氧化生成芳香β-咔啉类产物。该方法在生物碱合成中得到了应用，证明了其在尤迪斯通明素Y1至Y7的全合成中的实用性。

  DOI：

  10.1039/c3ob40661j
• 作为产物：
  描述：

  L-色氨酸 在 氯化亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 methyl 1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives

  摘要：

  Synthesis of 13 different tetrahydro-beta-carbolines (THBC) was accomplished by applying the Pictet-Spengler reaction with seven aldehydes, which have been coupled with tryptamine (6) and L-tryptophan methyl ester (7), respectively. The resulting products represent analogues of strictosidine (1) and carboxystrictosidine (5). They were investigated with respect to possible effects on herbivores in feeding bioassays upon the generalist Spodoptera littoralis. Maximum inhibition averages were 42% after four and 46% after six days for the most effective product (19) at 1000 ppm. Additionally, the frass of this particular bioassay was investigated via HPLC-UV for THBC digestion. All synthesized THBCs were also tested for their radical scavenger activity by monitoring their interaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 16-20, 24 and 25 exhibited radical scavenging activity, ranging from 50% to 74% compared to that of a-tocopherol. All results were discussed with respect to possible contributions of tetrahydro-beta-carboline moieties in bioactivities of strictosidine (1) and its biodegradation products. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.028

文献信息

• Synthesis of tetrahydro-β-carbolinediketopiperazines in [bdmim][PF6] ionic liquid accelerated by controlled microwave heating
  作者：Ya-Hew Yen、Yen-Ho Chu

  DOI：10.1016/j.tetlet.2004.09.056

  日期：2004.10

  Because of their negligible vapor pressures and large dipoles, ionic liquids are excellent media for microwave-accelerated organic reactions. Using low-power microwave irradiation in the new [bdmim][PF6] ionic liquid with temperature controlled at 60degreesC, a three-step synthesis (Pictet-Spengler, Schotten-Baumann, and intramolecular ester amidation) of tetraliydro-beta-carboline-diketopiperazines starting from tryptophan methyl ester was achieved with good isolated yields (49-69%) in only 5 min. (C) 2004 Elsevier Ltd. All rights reserved.
• The Synthesis of Derivatives of β-Carboline. II. Syntheses from dl-Tryptophan and Aldehydes¹
  作者：H. R. Snyder、Corwin H. Hansch、Leon Katz、Stanley M. Parmerter、Earl C. Spaeth

  DOI：10.1021/ja01181a063

  日期：1948.1
• Pictet-Spengler reactions in aprotic media. Stereospecificity in the Pictet-Spengler reaction
  作者：Joseph Sandrin、Sean P. Hollinshead、James M. Cook

  DOI：10.1021/jo00284a049

  日期：1989.11
• SANDRIN, JOSEPH;HOLLINSHEAD, SEAN P.;COOK, JAMES M., J. ORG. CHEM., 54,(1989) N3, C. 5636-5640
  作者：SANDRIN, JOSEPH、HOLLINSHEAD, SEAN P.、COOK, JAMES M.

  DOI：——

  日期：——