8-methyl-l-azabicyclo[4.3.0]nonan-9-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: 8-methyl-l-azabicyclo[4.3.0]nonan-9-one
• 英文别名: 2-methylhexahydroindolizin-3(2H)-one；2-methyl-3-indolizidone；6-methyl-1,2,3,4,5,6-hexahydro-(7H)-cyclopentapyridine-7-one；2-methyl-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: UOFUOAIIISLJOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-溴-1-己烯 在 苯磺酰基叠氮化物 、 indium 、 di-tert-butoxydiazene 、 六正丁基二锡 、 氯化铵 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 8-methyl-l-azabicyclo[4.3.0]nonan-9-one
  参考文献：
  名称：

  Radical Carboazidation of Alkenes: An Efficient Tool for the Preparation of Pyrrolidinone Derivatives

  摘要：

  DOI：

  10.1002/1521-3773(20020916)41:18<3460::aid-anie3460>3.0.co;2-6

文献信息

• Efficient and Regioselective 9-<i>Endo</i> Cyclization of α-Carbamoyl Radicals
  作者：Liyan Song、Kun Liu、Chaozhong Li

  DOI：10.1021/ol201180g

  日期：2011.7.1

  With the promotion of Lewis acid BF3•OEt2, various N-(hex-5-enyl)-2-iodoalkanamides underwent efficient and regioselective 9-endo iodine-atom-transfer radical cyclization reactions at room temperature. The cyclized products were readily converted to the corresponding azonan-2-ones by reduction with Bu3SnH or to hexahydroindolizin-3(5H)-ones by treatment with aqueous Na2CO3 in a one-pot, two-stage manner

  随着路易斯酸BF 3 •OEt 2的促进，在室温下，各种N-（hex-5-enyl）-2-iodaalkanamides进行了有效和区域选择性9-内碘原子转移自由基的环化反应。通过用一锅，两步方式用Na 2 CO 3水溶液处理，通过用Bu 3 SnH还原，可以容易地将环化产物转化为相应的氮杂-2-酮，或将其通过Na 2 CO 3水溶液处理而转化为六氢吲哚嗪-3（5 H）-酮。
• Formation of lactams via photoelectron-transfer catalyzed reactions of N-allylamines with α,β-unsaturated esters
  作者：Suresh Das、J.S. Dileep Kumar、Kalchar Shivaramayya、Manapurathu V. George

  DOI：10.1016/0040-4020(96)00022-1

  日期：1996.3

  photosensitized reactions of a few N-allylamines with α,β-unsaturated esters have been investigated. These reactions led predominantly to the formation of lactams along with trace amounts of products arising out of tandem radical addition reactions. A mechanism is proposed involving the rearrangement of the α-aminoallyl radical, initially generated via anthraquinone photosensitized reactions, to α-aminoalkyl

  研究了一些N-烯丙胺与α，β-不饱和酯的蒽醌光敏反应。这些反应主要导致内酰胺的形成以及由串联自由基加成反应产生的痕量产物。提出了一种机制，该机制涉及将最初通过蒽醌光敏反应产生的α-氨基烯丙基自由基重排为α-氨基烷基自由基。这些自由基与α，β-不饱和酯的后续反应可导致观察到产物。
• Nakao, Yoshiaki; Idei, Hiroaki; Kanyiva, Kyalo Stephen, Journal of the American Chemical Society, 2009, vol. 131, p. 5070 - 5071
  作者：Nakao, Yoshiaki、Idei, Hiroaki、Kanyiva, Kyalo Stephen、Hiyama, Tamejiro

  DOI：——

  日期：——
• Radical Carboazidation:  Expedient Assembly of the Core Structure of Various Alkaloid Families
  作者：Philippe Panchaud、Cyril Ollivier、Philippe Renaud、Sarunas Zigmantas

  DOI：10.1021/jo035843y

  日期：2004.4.1

  A procedure for one-pot intermolecular radical addition of 2-iodoesters to terminal alkenes followed by azidation of the radical adduct has been developed. This sequential reaction represents an alkene carboazidation process. Its efficacy is demonstrated by the two-step preparation of various lactams such as pyrrolidinones, pyrrolizidinones, and indolizidinones. An easy access to spirolactams bearing an amino-substituted quaternary carbon center is also described. These compounds are important building blocks for the synthesis of numerous alkaloids such as, for instance, FR901483.
• Photocatalyzed multiple additions of amines to .alpha.,.beta.-unsaturated esters and nitriles
  作者：Suresh Das、J. S. Dileep Kumar、K. George Thomas、K. Shivaramayya、M. V. George

  DOI：10.1021/jo00082a021

  日期：1994.2

  Photoelectron-transfer-catalyzed intermolecular carbon-carbon bond formation of primary, secondary, and tertiary amines with alpha,beta-unsaturated esters and nitriles using photosensitizers such as anthraquinone, acridone, and dicyanoanthracene has been investigated. The addition of alpha-aminoalkyl radicals, generated via photoelectron-transfer processes, to olefinic substrates and the subsequent 1,5-hydrogen abstraction reactions of the amine-olefin adduct radicals lead to a number of interesting multiple-olefin-added products. The adducts of the primary and secondary amines with alpha beta-unsaturated esters undergo further cyclizations to give spiro and cyclic lactams, respectively.