2-methylhexahydro-3H-pyrrolizin-3-one | 86954-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: 2-methylhexahydro-3H-pyrrolizin-3-one
• 英文别名: 2-Methyl-3-oxohexahydropyrrolizine；2-methyl-3-pyrrolizidone；2-methyl-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• CAS: 86954-03-2
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: HCQDSWXPQNGLFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  5-溴-1-戊烯 在 苯磺酰基叠氮化物 、 indium 、 六正丁基二锡 、 氯化铵 、 反式-二叔丁基连二次硝酸酯 作用下， 以 乙醇 、 苯 为溶剂， 反应 6.0h， 生成 2-methylhexahydro-3H-pyrrolizin-3-one
  参考文献：
  名称：

  Radical Carboazidation:  Expedient Assembly of the Core Structure of Various Alkaloid Families

  摘要：

  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.

  DOI：

  10.1021/jo035843y

文献信息

• 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。
• HETEROCYCLIC TYPE CINNAMIDE DERIVATIVE
  申请人：Kimura Teiji

  公开号：US20090203697A1

  公开（公告）日：2009-08-13

  Disclosed is a compound represented by the formula (I) below or a pharmacologically acceptable salt thereof. Also disclosed is a use of the compound or salt as a pharmaceutical product. (In the formula, Ar 1 represents a triazolyl group or the like which may be substituted with a C 1-6 alkyl group or the like; Ar 2 represents a phenyl group or the like which may be substituted with a C 1-6 alkoxy group or the like; X 1 represents —CR 3 ═CR 4 — (wherein R 3 and R 4 respectively represent a C 1-6 alkyl group or the like); and R 1 and R 2 respectively represent a C 1-6 alkyl group or the like.)

  本发明公开了下式(I)所表示的化合物或其药学上可接受的盐。同时，本发明还公开了该化合物或盐作为药物产品的用途。（其中，Ar1代表三唑基或类似物，可以用C1-6烷基或类似物取代；Ar2代表苯基或类似物，可以用C1-6烷氧基或类似物取代；X1代表—CR3═CR4—（其中，R3和R4分别代表C1-6烷基或类似物）；而R1和R2分别代表C1-6烷基或类似物。）
• Palladium-catalyzed carbonylation. A new synthesis of .alpha.-methylene .gamma.-, .delta.-, .epsilon.-lactams and lactones including bicyclic lactams of pyrrolizidine and indolizidine skeletons
  作者：Miwako Mori、Yumiko Washioka、Takao Urayama、Kagari Yoshiura、Katsumi Chiba、Yoshio Ban

  DOI：10.1021/jo00170a037

  日期：1983.11
• Radical Carboazidation of Alkenes: An Efficient Tool for the Preparation of Pyrrolidinone Derivatives
  作者：Philippe Renaud、Cyril Ollivier、Philippe Panchaud

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

  日期：2002.9.16
• 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.