3-methyl-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydrocarbazole | 155961-91-4

• 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: 3-methyl-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydrocarbazole
• 英文别名: 8-methyl-5,7,8,9-tetrahydro-6H-1,3-dioxolo[4,5-b]carbazol-6-one；8-methyl-8,9-dihydro-5H-[1,3]dioxolo[4,5-b]carbazol-6(7H)-one；8-Methyl-8,9-dihydro-5h-[1,3]dioxolo[4,5-b]carbazol-6(7h)-one；6-methyl-5,6,7,9-tetrahydro-[1,3]dioxolo[4,5-h]carbazol-8-one
• CAS: 155961-91-4
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: QBVBZGGTCROUFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydrocarbazole 在 氢氧化钾 、 一水合肼 作用下， 以 乙二醇 为溶剂， 生成 3-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  Clausenalene，一种来自七叶 Clausena heptaphylla 的咔唑生物碱

  摘要：

  摘要 从七叶云杉的茎皮中分离得到一种新的咔唑生物碱，命名为黄花烯，从物理、化学证据和合成上确定其结构为3-甲基-6,7-亚甲二氧基咔唑。这是来自植物来源的亚甲二氧基咔唑生物碱的首次报道。

  DOI：

  10.1016/0031-9422(93)85437-v
• 作为产物：
  描述：

  2-(hydroxymethylidene)-5-methylcyclohexanone 在 盐酸 、 sodium acetate 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 0.08h， 生成 3-methyl-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  Clausenalene，一种来自七叶 Clausena heptaphylla 的咔唑生物碱

  摘要：

  摘要 从七叶云杉的茎皮中分离得到一种新的咔唑生物碱，命名为黄花烯，从物理、化学证据和合成上确定其结构为3-甲基-6,7-亚甲二氧基咔唑。这是来自植物来源的亚甲二氧基咔唑生物碱的首次报道。

  DOI：

  10.1016/0031-9422(93)85437-v

文献信息

• A Tandem Reduction-Oxidation Protocol for the Conversion of 1-Keto-1,2,3,4-tetrahydrocarbazoles to Carbazoles via Tosylhydrazones through Microwave Assistance: Efficient Synthesis of Glycozoline, Clausenalene, Glycozolicine, and Deoxycarbazomycin B and th
  作者：Suchandra Chakraborty、Gautam Chattopadhyay、Chandan Saha

  DOI：10.1002/jhet.999

  日期：2013.1

  methodology for the synthesis of carbazoles from 1‐keto‐1,2,3,4‐tetrahydrocarbazoles via the corresponding tosylsulfonhydrazones by a one‐pot tandem reduction–oxidation protocol using a combination of NaBH4 and Pd–C on MgSO4·7H2O, a solid support, under microwave is developed. The reaction is successfully extended toward the synthesis of several naturally occurring carbazole alkaloids, namely 3‐methylcarbazole

  一种新颖高效的方法，通过NaBH 4和Pd-C的组合，通过一锅串联还原-氧化方案，通过相应的甲苯磺酰基hydr肼，通过相应的甲苯磺酰基hydr，由1-酮，1,2,3,4-四氢咔唑合成咔唑在微波作用下形成了4 ·7H 2 O（一种固体支持物）。该反应已成功地扩展到几种天然存在的咔唑生物碱的合成，即3-甲基咔唑，糖唑啉，黄嘌呤，糖唑啉，墨瑞福林A和脱氧咔唑霉素B（一种已知具有良好抗菌活性的咔唑衍生物）。
• Monitoring the Competence of a New Keto-tetrahydrocarbazole Based Fluorosensor Under Homogeneous, Micro-Heterogeneous and Serum Albumin Environments
  作者：Amrit Krishna Mitra、Abhishek Sau、Subhas Chandra Bera、Suchandra Chakraborty、Chandan Saha、Samita Basu

  DOI：10.1007/s10895-015-1685-z

  日期：2015.11

  We present here a detailed photophysical study of a recently synthesised fluorophore 8-methyl-8,9-dihydro-5H-[1,3]dioxolo[4,5-b]carbazol-6(7H)-one. This is a synthetic precursor of bio-active carbazole skeleton Clausenalene. Spectroscopic investigation of the fluorophore has been carried out in different protic and aprotic solvents, as well as in binary solvent mixtures, using absorption, steady-state and time-resolved fluorescence techniques. This fluorophore is particularly responsive to the hydrogen bonding nature as well as polarity of the solvent molecules. When considered in micelles and β-cyclodextrin, this behaves as a reporter of its immediate microenvironment. Steady state and time resolved fluorometric and circular dichroism techniques have been used to explore the binding interaction of the fluorophore with transport proteins, bovine serum albumin and human serum albumin. The probable binding sites of the fluorophore in the proteinous environments have been evaluated from fluorescence resonance energy transfer study. Laser flash photolysis experiments also have been performed to observe the triplet excited state interaction between the fluorophore and albumin proteins.

  我们在此对最近合成的荧光团8-甲基-8,9-二氢-5H-[1,3]二氧杂环戊烯并[4,5-b]咔唑-6(7H)-酮进行详细的光物理研究。这是生物活性咔唑骨架克劳森烯的合成前体。我们使用吸收、稳态和时分辨荧光技术，在不同的亲核和非亲核溶剂以及二元溶剂混合物中对荧光团进行了光谱研究。这种荧光团对溶剂分子的氢键性质和极性特别敏感。当考虑在胶束和β-环糊精中时，它就像其直接微环境的报告器。稳态和时分辨荧光和圆二色性技术已被用于探索荧光团与转运蛋白、牛血清白蛋白和人类血清白蛋白的结合相互作用。通过荧光共振能量转移研究，评估了荧光团在蛋白质环境中的可能结合位点。我们还进行了激光闪光光解实验，以观察荧光团和白蛋白之间的三重态激发态相互作用。
• Chakraborty, Suchandra; Chattopadhyay, Gautam; Saha, Chandan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 2, p. 201 - 206
  作者：Chakraborty, Suchandra、Chattopadhyay, Gautam、Saha, Chandan

  DOI：——

  日期：——
• Palladium-catalyzed syntheses of tetrahydrocarbazolones as advanced intermediates to carbazole alkaloids
  作者：Tricia L. Scott、Xiaomei Yu、Sobha P. Gorugantula、Grissell Carrero-Martínez、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2006.08.100

  日期：2006.11

  Two sequential palladium-catalyzed reactions, an intermolecular Stille cross-coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation, have been employed as the key synthetic steps toward six tetrahydrocarbazolones. The products are advanced intermediates toward a number of naturally occurring carbazole alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.
• Clausenalene, a carbazole alkaloid from Clausena heptaphylla
  作者：P. Bhattacharyya、G.K. Biswas、A.K. Barua、C. Saha、I.B. Roy、B.K. Chowdhury

  DOI：10.1016/0031-9422(93)85437-v

  日期：1993.4

  Abstract A new carbazole alkaloid designated as clausenalene was isolated from the stem bark of Clausena heptaphylla and its structure established as 3-methyl-6,7-methylenedioxy carbazole from physical, chemical evidence and synthesis. This is the first report of a methylenedioxy carbazole alkaloid from a plant source.

  摘要 从七叶云杉的茎皮中分离得到一种新的咔唑生物碱，命名为黄花烯，从物理、化学证据和合成上确定其结构为3-甲基-6,7-亚甲二氧基咔唑。这是来自植物来源的亚甲二氧基咔唑生物碱的首次报道。