vulcanine

• 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: vulcanine
• 英文别名: 1-(2-methylprop-1-en-1-yl)-9H-pyrido[3,4-b]indole；1-(2-Methyl-1-propen-1-yl)-9h-pyrido[3,4-b]indole；1-(2-methylprop-1-enyl)-9H-pyrido[3,4-b]indole
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: UOPKNMSNJLVJOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  vulcanine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以32 mg的产率得到1-isobutyl-9H-β-carboline
  参考文献：
  名称：

  Vulcanine，一种来自 Haplophyllum vulcanicum 的 β-咔啉生物碱

  摘要：

  从 Haplophyllum vulcanicum 中分离出一种新型 β-咔啉生物碱 vulcanine (1-(2-methyl-1-propenyl)-β-carboline) 标志着该骨架在该属中的首次出现。

  DOI：

  10.1016/s0031-9422(96)00444-x
• 作为产物：
  描述：

  1-(2-methyl-1-propenyl)-1,2,3,4-tetrahydro-β-carboline 在 sodium hydroxide 、 次氯酸叔丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 64.0h， 以51%的产率得到vulcanine
  参考文献：
  名称：

  Creation of New Promoters for Plant’s Root Growth: Its Application for the Syntheses of Vulcanine and Borreline, and for Combating Desertification at Gobi Desert in Inner Mongolia

  摘要：

  Various new 2-substituted indole-3-carbaldehydes are prepared. Structurally related alkaloids, vulcanine and borreline, are synthesized as well. Among the compounds, 2-haloindole-3-carbaldehydes are found to be potent promoters of plant's root growth. Its successful preliminary application is reported for making Gobi desert in Inner Mongolia full of plant.

  DOI：

  10.3987/com-07-s(u)31

文献信息

• An Alternative to Pictet-Gams Reaction Triggered by Hendrickson Reagent: Isoquinolines and β-Carbolines from Amides
  作者：Shaozhong Wang、Mengde Wu

  DOI：10.1055/s-0029-1217138

  日期：2010.2

  The Hendrickson reagent derived from triflic anhydride and triphenylphosphine oxide exhibited high oxophilicity and induced the intramolecular cyclization of β-arylethylamides perfectly. Thus, a one-pot protocol to access isoquinoline and β-carboline was developed involving cyclization followed by oxidative aromatization. Hendrickson reagent - isoquinoline - β-carboline - β-arylethylamide - manganese(IV)

  衍生自三氟甲磺酸酐和三苯基氧化膦的亨德里克森试剂表现出高的亲氧性，并完美地诱导了β-芳基乙酰胺的分子内环化。因此，开发了一种一锅法访问异喹啉和β-咔啉，该方法涉及环化，然后进行氧化芳构化。 亨德里克森试剂-异喹啉-β-咔啉-β-芳基乙酰胺-氧化锰
• Creation of New Promoters for Plant’s Root Growth: Its Application for the Syntheses of Vulcanine and Borreline, and for Combating Desertification at Gobi Desert in Inner Mongolia
  作者：Masanori Somei、Shinsuke Sayama、Katsumi Naka、Kotaro Shinmoto、Fumio Yamada

  DOI：10.3987/com-07-s(u)31

  日期：——

  Various new 2-substituted indole-3-carbaldehydes are prepared. Structurally related alkaloids, vulcanine and borreline, are synthesized as well. Among the compounds, 2-haloindole-3-carbaldehydes are found to be potent promoters of plant's root growth. Its successful preliminary application is reported for making Gobi desert in Inner Mongolia full of plant.
• Vulcanine, a β-carboline alkaloid from Haplophyllum vulcanicum
  作者：Tekant Gözler、Belkis Gözler、Anthony Linden、Manfred Hesse

  DOI：10.1016/s0031-9422(96)00444-x

  日期：1996.12

  The isolation of a novel β-carboline alkaloid, vulcanine (1-(2-methyl-1-propenyl)-β-carboline) from Haplophyllum vulcanicum marks the first occurrence of this skeleton in the genus.

  从 Haplophyllum vulcanicum 中分离出一种新型 β-咔啉生物碱 vulcanine (1-(2-methyl-1-propenyl)-β-carboline) 标志着该骨架在该属中的首次出现。