1-(4-chlorobutyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 763883-25-6

• 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: 1-(4-chlorobutyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 763883-25-6
• 化学式: C₁₅H₁₉ClN₂
• 分子量: 262.782
• InChiKey: FQBICADTBILMHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobutyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 1,2,3,4,6,7,12,12b-八氢吲哚并(2,3-a)喹嗪
  参考文献：
  名称：

  Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products

  摘要：

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

  DOI：

  10.1021/jo4023149
• 作为产物：
  描述：

  1-(tert-butyldimethylsilyloxy)-4-pentyne 在 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 氯化亚砜 、 palladium 10% on activated carbon 、 盐酸羟胺 、 methyl orange 、 水 、 氢气 、 sodium acetate 、 三氧化硫吡啶 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 二甲基亚砜 、 异丙胺 、 三乙胺 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 乙酸乙酯 、 异丙醇 、 叔丁醇 为溶剂， 反应 28.0h， 生成 1-(4-chlorobutyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products

  摘要：

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

  DOI：

  10.1021/jo4023149

文献信息

• Verfahren zur Herstellung von 1-(Halogenalkyl)-1,2,3,4-tetrahydro-beta-carbolinen
  申请人：BASF Aktiengesellschaft

  公开号：EP0101934A1

  公开（公告）日：1984-03-07

  Es werden Salze von 1,2,3,4-Tetrahydro-ß-carbolinen der Formel I worin R ein Wasserstoff- oder Halogenatom oder eine C1-C4-Alkyl-, C1-C4-Alkoxy- oder Trifluormethylgruppe, X ein Halogenatom und n eine ganze Zahl von 2 bis 5 bedeuten, sowie deren Herstellung beschrieben. Die Verbindungen sind Zwischenprodukte zur Herstellung pharmakologisch aktiver Substanzen.

  式 I 的 1,2,3,4-四氢-ß-羰基化合物的盐类 其中 R 是氢原子、卤素原子或 C1-C4- 烷基、C1-C4-烷氧基或三氟甲基、 X 是卤素原子，以及 n 是 2 至 5 的整数 的化合物及其制备方法。这些化合物是生产药理活性物质的中间体。
• US4565870A
  申请人：——

  公开号：US4565870A

  公开（公告）日：1986-01-21
• Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products
  作者：Isabelle Dion、Jean-François Vincent-Rocan、Lei Zhang、Pamela H. Cebrowski、Marie-Eve Lebrun、Jennifer Y. Pfeiffer、Anne-Catherine Bédard、André M. Beauchemin

  DOI：10.1021/jo4023149

  日期：2013.12.20

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.