4-(2,3,4,9-四氢-1H-beta-咔啉-1-基)-1-丁醇 | 94071-13-3

• 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
• 中文名称: 4-(2,3,4,9-四氢-1H-beta-咔啉-1-基)-1-丁醇
• 英文名称: 1-(4-hydroxybutyl)-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 1-(4-hydroxybutyl)-3,4-dihydro-1H-pyrido[3,4-b]indole；4-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-butan-1-ol；2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-butanol；2,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indole-1-butanol；4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)butan-1-ol
• CAS: 94071-13-3
• 化学式: C₁₅H₂₀N₂O
• 分子量: 244.337
• InChiKey: JGXRNUZQPOXGCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  48
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-(2,3,4,9-四氢-1H-beta-咔啉-1-基)-1-丁醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到1,2,3,4,6,7,12,12b-八氢吲哚并(2,3-a)喹嗪
  参考文献：
  名称：

  The use of triphenylphosphine/diethyl azodicarboxylate (dead) for the cyclization of 1,4- and 1,5-amino alcohols

  摘要：

  Application of the Mitsunobu reagent to the cyclization of 1,4- and 1,5-amino alcohols provided an assortment of azacycles in good to excellent yield.

  DOI：

  10.1016/0040-4039(91)80843-u
• 作为产物：
  描述：

  1-(tert-butyldimethylsilyloxy)-4-pentyne 在 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 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 25.0h， 生成 4-(2,3,4,9-四氢-1H-beta-咔啉-1-基)-1-丁醇
  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

• Enzyme catalysed oxidation of nazlinin and nazlinin derivatives. Characterisation of the reaction products
  作者：Elisabeth Cheng、Jens Botzem、Martin J. Wanner、Brigitte E.A. Burm、Gerrit-Jan Koomen

  DOI：10.1016/0040-4020(96)00286-4

  日期：1996.5

  catalyse the oxidative transformation of Nitraria alkaloids. Nazlinin yielded indoloquinolizidine 4, an alkaloid which has been obtained as a natural product from Nitraria plant extracts. Oxidative deamination of 1-(4-butylamino)-β-carboline 10 with PKDO yielded an unstable aldehyde (11), which cyclised to a new, arborescidine-type azepine (12). Addition of alcohol dehydrogenase during the oxidative deamination

  猪肾脏二胺氧化酶（PKDO）被用来催化白屈菜生物碱的氧化转化。Nazlinin产生吲哚并喹喔啉4，这是一种生物碱，是从Nitraria植物提取物中得到的天然产物。1-（4-丁基氨基）-β-咔啉10用PKDO进行氧化脱氨基反应生成不稳定的醛（11），然后将其环化为新的阿波西啶型氮杂环庚烷（12）。在氧化脱氨过程中添加醇脱氢酶可将醛原位还原为相应的醇13。托帕醌类似物9这些伯胺作为化学计量的氧化剂有效。通过与化学合成的化合物进行比较来表征酶反应产物。
• 118. The constitution of yohimbine and related alkaloids. Part VI. The synthesis of 1 : 2 : 3 : 4 : 6 : 7 : 12 : 12b-octahydro-2-ketoindolo-(2 : 3-a)pyridocoline and 1 : 2 : 3 : 4-tetrahydroindolo(2 : 3-a)pyridocoline
  作者：L. H. Groves、G. A. Swan

  DOI：10.1039/jr9520000650

  日期：——
• The use of triphenylphosphine/diethyl azodicarboxylate (dead) for the cyclization of 1,4- and 1,5-amino alcohols
  作者：Ronald C. Bernotas、Rowena V. Cube

  DOI：10.1016/0040-4039(91)80843-u

  日期：1991.1

  Application of the Mitsunobu reagent to the cyclization of 1,4- and 1,5-amino alcohols provided an assortment of azacycles in good to excellent yield.
• 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.