1,4-萘二酮并,8-(1H-吲哚-3-基)-2-甲氧基-6-甲基- | 128508-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,4-萘二酮并,8-(1H-吲哚-3-基)-2-甲氧基-6-甲基-
• 英文名称: murrapanine
• 英文别名: 8-(1H-indol-3-yl)-2-methoxy-6-methylnaphthalene-1,4-dione
• CAS: 128508-22-5
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: VQJFSWASPVFXFY-UHFFFAOYSA-N

物化性质

• 熔点：
  278-280 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  621.6±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-[(4-甲基苯基)磺酰]-1H-吲哚-3-甲醛 在 sodium hydroxide 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 26.0h， 生成 1,4-萘二酮并,8-(1H-吲哚-3-基)-2-甲氧基-6-甲基-
  参考文献：
  名称：

  Murrapanine（一种新型的骨骼吲哚-萘醌生物碱）的结构和合成以及来自Murraya paniculata var的细胞毒性因子。掌果

  摘要：

  从Murraya paniculata var的根皮中分离出一种新型的骨架细胞毒性吲哚-萘醌生物碱murrapanine 。通过光谱数据和单晶X射线分析建立了掌果及其结构。还描述了由吲哚-3-醛合成尿嘧啶的方法。

  DOI：

  10.1016/s0040-4039(00)70641-1

文献信息

• Reaction of (dimethylvinylidene)carbene with indole-3-carbaldehyde and its application in the synthesis of β-(dehydroprenyl)indole-based natural products
  作者：Jyh-Horng Sheu、Chun-An Chen、Buo-Horng Chen

  DOI：10.1039/a808733d

  日期：——

  Reaction of (dimethylvinylidene)carbene with indole-3-carbaldehyde gives various dehydroprenyl-based indoles. Efficient synthesis of the indole natural products yuehchukene and murrapanine, using this reaction as a key step, is also described.

  (二甲基亚乙烯基)碳烯与吲哚-3-甲醛反应生成了各种脱水丙烯基吲哚。此外，还介绍了以该反应为关键步骤，高效合成吲哚类天然产物月桂烯和毛蕊花宁的过程。
• Sheu, Jyh-Horng; Chen, Yua-Kuang; Chung, Huey-Fen, Journal of the Chemical Society. Perkin transactions I, 1998, # 12, p. 1959 - 1965
  作者：Sheu, Jyh-Horng、Chen, Yua-Kuang、Chung, Huey-Fen、Lin, Song-Fang、Sung, Ping-Jyun

  DOI：——

  日期：——
• Synthesis of Yuehchukene Analogues, Murrapanine and Normurrapanine Utylizing Thermal Reaction of b-(1-Hydroxybutenyl)indoles under Neutral Reaction Conditions
  作者：Jyh-Horng Sheu、Yua-Kuang Chen、Huey-Fen Chung、Ping-Jyun Sung、Song-Fong Lin

  DOI：10.3987/com-96-7507

  日期：——

  beta-(1-Hydroxybutenyl)indoles, which were prepared in high yields from indole-3-carboxaldehyde, could be converted into yuehchukene analogues(8a, b) murrapanine (9a) and normurrapanine (9b) in one step under thermal-induced reaction conditions in neutral solution of ethylene glycol and water. beta-(1-Hydroxybutenyl)indoles are supposed to be dehydrated to 1-(beta-indolyl)-1,3-butadienes which react further to yuehchukene analogues via a Diels-Alder pathway. Murrapanine and normurrapanine showed a cytotoxicity toward KB cells.
• WU, TIAN-SHUNG;LIOU, MEEI-JEN;LEE, CHWAN-JEN;JONG, TING-TING;MCPHAIL, AND+, TETRAHEDRON LETT., 30,(1989) N8, C. 6649-6652
  作者：WU, TIAN-SHUNG、LIOU, MEEI-JEN、LEE, CHWAN-JEN、JONG, TING-TING、MCPHAIL, AND+

  DOI：——

  日期：——
• Structure and synthesis of murrapanine, a novel skeletal indole-naphthoquinone alkaloid and cytotoxic principal from Murraya paniculata var. omphalocarpa
  作者：Tian-Shung Wu、Meei-Jen Liou、Chwan-Jen Lee、Ting-Ting Jong、Andrew T. McPhail、Donald R. McPhail、Kuo-Hsiung Lee

  DOI：10.1016/s0040-4039(00)70641-1

  日期：——

  A novel skeletal cytotoxic indole-naphthoquinone alkaloid, murrapanine, has been isolated from the root bark of Murraya paniculata var. omphalocarpa and its structure has been established from spectral data and single-crystal X-ray analysis; the synthesis of murrapanine from indole-3-aldehyde is also described.

  从Murraya paniculata var的根皮中分离出一种新型的骨架细胞毒性吲哚-萘醌生物碱murrapanine 。通过光谱数据和单晶X射线分析建立了掌果及其结构。还描述了由吲哚-3-醛合成尿嘧啶的方法。