3,4-二氢-9H-吡啶并[3,4-b]吲哚N-氧化物 | 112863-43-1

• 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
• 中文名称: 3,4-二氢-9H-吡啶并[3,4-b]吲哚N-氧化物
• 英文名称: 3,4-dihydro-9H-pyrido[3,4-b]indole N-oxide
• CAS: 112863-43-1
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: JONJIFGESBUDDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,4-二氢-9H-吡啶并[3,4-b]吲哚N-氧化物 以 xylene 、 苯 为溶剂， 反应 72.0h， 生成 spiro[cyclopropane-1,1'-(1,2,3,4,5,6,7,12,12b-octahydropyrido[2,1-a]-β-carbolin)]-2'-one
  参考文献：
  名称：

  Studies on the Synthesis of Aza Analogues of Illudins by Cycloadditions to Highly Strained Methylenecyclopropanes

  摘要：

  A series of 3-spirocyclopropane-tetrahydropyrid-4-ones has been synthesized by the method consisting of nitrone cycloaddition to bicyclopropylidene and thermal rearrangement of the adducts. Regioisomeric 5-spirocyclopropanetetrahydropyrid-4-ones and 5-spirocyclopropanedihydropyrid-4 ones were instead obtained by cycloaddition of nitrones and nitrile oxides, respectively, to methylenespiropentane, followed by thermal rearrangement. Methylenedispiro[2.0.2.1]heptane gave, in turn, 5,6-bis(spirocyclopropane)dihydropyrid-4 The new compounds were prepared as simple aza analogues of the cytotoxic natural products illudins and ptaquiloside in order to study their activity in cleaving a DNA plasmid. The activities shown by several of the compounds are moderate, but from a comparative qualitative analysis of the results a useful structure-activity relationship for this new class of compounds could be derived.

  DOI：

  10.1021/jo990873f
• 作为产物：
  描述：

  1,2,3,4-四氢-9H-吡啶[3,4-B]并吲哚 在 Na₂WO₅*2H₂O 、 双氧水 作用下， 以 甲醇 、 丙酮 为溶剂， 以66%的产率得到3,4-二氢-9H-吡啶并[3,4-b]吲哚N-氧化物
  参考文献：
  名称：

  1,3-Dipolar Cycloaddition Reaction of 3,4-Dihydro-β-carboline 2-Oxide

  摘要：

  3,4-二氢-β-咔啉2-氧化物(1) 与各种亲偶极试剂进行1,3-偶极[3+2] 环加成反应，得到相应的环加合物2-26′。研究了这些环加成反应的区域选择性和立体选择性。

  DOI：

  10.1055/s-1998-2044

文献信息

• Methyltrioxorhenium-Catalyzed Oxidation of Secondary and Primary Amines with Hydrogen Peroxide
  作者：Shigekazu Yamazaki

  DOI：10.1246/bcsj.70.877

  日期：1997.4

  The methyltrioxorhenium-catalyzed oxidation of secondary amines and primary amines with hydrogen peroxide has been carried out. The oxidation of secondary amines afforded nitrones in good-to-excellent yield. Benzylamines were selectively oxidized to oximes, while general primary alkylamines possessing the α-C–H bond gave mixtures of oximes, nitroso dimers, and azoxy compounds.

  用过氧化氢对仲胺和伯胺进行了甲基三氧铼催化氧化。仲胺的氧化以良好至极好的收率提供硝酮。苄胺被选择性氧化为肟，而具有 α-C-H 键的一般伯烷基胺生成肟、亚硝基二聚体和氧化偶氮化合物的混合物。
• Thermal Isomerization of 1,3-Dipolar Cycloadducts of 3,4-Dihydro-β-carboline 2-Oxide
  作者：Satoshi Moriyama、Yannick Vallée

  DOI：10.1002/(sici)1099-0690(199807)1998:7<1391::aid-ejoc1391>3.0.co;2-g

  日期：1998.7

  The thermal isomerization of the 1,3-dipolar cycloadducts of 3,4-dihydro-β-carboline 2-oxide is studied using 1H-NMR spectroscopy. Stereoisomerizations of the cis or syn cycloadducts with dipolarophiles such as methyl crotonate, methyl cinnamate, and methyl methacrylate into the trans or anti cycloadducts are observed. On the other hand, regioisomerization of the 1-substituted cycloadduct with nitroethylene

  使用 1 H-NMR 光谱研究了 3,4-二氢-β-咔啉 2-氧化物的 1,3-偶极环加合物的热异构化。观察到顺式或顺式环加合物与偶极体（例如巴豆酸甲酯、肉桂酸甲酯和甲基丙烯酸甲酯）的立体异构化成反式或反式环加合物。另一方面，还观察到 1-取代的环加合物与硝基乙烯的区域异构化成 2-取代的环加合物。
• Silylacetate-promoted addition reaction of isocyanides to nitrones: effective synthesis of C(1)-carboxamide derivatives
  作者：Takahiro Soeta、Siming Yao、Hirokazu Sugiyama、Yutaka Ukaji

  DOI：10.1039/d3ob01777j

  日期：——

  We report an efficient method for the synthesis of C(1)-carboxamide derivatives by adding isocyanides to 3,4-dihydroisoquinoline N-oxides and 3,4-dihydro-β-carboline 2-oxide in the presence of TMSOAc. 3,4-Dihydroisoquinoline-1-carboxylamide derivatives and 9-dihydro-3H-pyrido[3,4-b]indole-1-carboxamide derivatives were obtained in reasonable yields. The method could be used to synthesize alangiobussine

  我们报道了一种在 TMSOAc 存在下将异氰化物添加到 3,4-二氢异喹啉N-氧化物和 3,4-二氢-β-咔啉 2-氧化物中合成 C(1)-甲酰胺衍生物的有效方法。以合理的收率获得了3,4-二氢异喹啉-1-甲酰胺衍生物和9-二氢-3H-吡啶并[3,4 -b ]吲哚-1-甲酰胺衍生物。该方法可用于合成生物碱alangiobussine，收率61%。
• Rearrangement of isoxazoline-5-spiro derivatives. 2. Synthesis and rearrangement of tetrahydroisoxazole-5-spirocyclopropanes. Preparation of precursors of quinolizine, isoquinoline, and indole alkaloids
  作者：Alberto Brandi、Sandro Garro、Antonio Guarna、Andrea Goti、Franca Cordero、Francesco De Sarlo

  DOI：10.1021/jo00246a008

  日期：1988.5
• BRANDI, ALBERTO;GARRO, SANDRO;GUARNA, ANTONIO;GOTI, ANDREA;CORDERO, FRANC+, J. ORG. CHEM., 53,(1988) N 11, 2430-2434
  作者：BRANDI, ALBERTO、GARRO, SANDRO、GUARNA, ANTONIO、GOTI, ANDREA、CORDERO, FRANC+

  DOI：——

  日期：——