1-(2,3-二氢-1H-吡咯里嗪-5-基)乙酮 | 55041-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 中文名称: 1-(2,3-二氢-1H-吡咯里嗪-5-基)乙酮
• 英文名称: 5-Acetyl-1,2-dihydro-3H-pyrrolo<1,2-a>pyrrole
• 英文别名: 5-Acetyl-2,3-dihydro-1H-pyrrolizin；1-(6,7-dihydro-5H-pyrrolizin-3-yl)-ethanone；5-acetyl-2,3-dihydro-1H-pyrrolizine；1-(6,7-dihydro-5H-pyrrolizin-3-yl)ethanone
• CAS: 55041-85-5
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: NWSCEJHRUVCUSX-UHFFFAOYSA-N

物化性质

• 沸点：
  290.4±28.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  45.5°C
• 保留指数：
  1335;1382;1354

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  2-乙酰基吡咯 在 氢氧化钾 、 双氧水 、 iron(II) sulfate 、 sodium iodide 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 7.17h， 生成 1-(2,3-二氢-1H-吡咯里嗪-5-基)乙酮
  参考文献：
  名称：

  Oxidative Radical Cyclization of (.omega.-Iodoalkyl)indoles and Pyrroles. Synthesis of (-)-Monomorine and Three Diastereomers

  摘要：

  Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeSO4:7H(2)O (1 equiv) in Dh ISO containing the N-(omega-iodoalkyl)indoles 4, 5, 11, and 13 effected oxidative radical cyclization to 6, 7, 14, and 15, respectively. The (omega-iodoalkyl)pyrroles 21, 22, 27, 38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 55 which, on catalytic reduction (H-2/Rh-A1(2)O(3)), gave a mixture of (-)-monomorine (40) and three of its diastereomers 56-58 (see, however, Note Added in Proof).

  DOI：

  10.1021/jo00088a029

文献信息

• Intramolecular radical acylation of 2-methylsulfonylpyrroles
  作者：Luis D. Miranda、Raymundo Cruz-Almanza、Abraham Alvarez-Garcı́a、Joseph M. Muchowski

  DOI：10.1016/s0040-4039(00)00342-7

  日期：2000.4

  Primary alkyl radicals generated (AIBN/Bu3SnH) from 1-(2- or 3-haloalkyl)-2-methylsulfonylpyrroles are intercepted by CO (80 atm), and the acyl radicals so produced undergo intramolecular oxidative cyclization at the α-position, giving bicyclic ketones with retention or loss of the sulfonyl moiety.

  由1-（2-或3-卤代烷基）-2-甲基磺酰吡咯生成的伯烷基自由基（AIBN / Bu 3 SnH）被CO（80 atm）截获，因此生成的酰基在α位进行分子内氧化环化，得到具有保留或丢失磺酰基部分的双环酮。
• Tobacco treatment
  申请人：British American Tobacco (Investments) Limited

  公开号：US10264813B2

  公开（公告）日：2019-04-23

  A process is provided for the treatment of tobacco. The process comprises securing the tobacco within a moisture-retaining material and exposing the tobacco material to an ambient processing temperature of above 55° C., with the tobacco having a packing density of at least 200 kg/m3 on a dry matter weight base at the start of the process and a moisture content of between about 10% and 23%. The treated tobacco may have desirable organoleptic properties.

  提供了一种处理烟草的工艺。该工艺包括将烟草固定在保湿材料中，并将烟草材料暴露在高于 55 摄氏度的环境加工温度下，在工艺开始时，烟草的包装密度至少为 200 千克/立方米（以干物质重量为基准），含水量约为 10%至 23%。经过处理的烟草可能具有理想的感官特性。
• Sweetener and flavor compositions, methods of making and methods of use thereof
  申请人：EPC Natural Products Co., Ltd.

  公开号：US11147295B2

  公开（公告）日：2021-10-19

  Sweetener and flavor compositions with improved taste profiles are disclosed. Also disclosed are methods of making and methods of using such sweetener and flavor compositions.

  本发明公开了具有改进口味特征的甜味剂和香料组合物。还公开了制作和使用这种甜味剂和香料组合物的方法。
• Tasteful natural sweetener and flavor
  申请人：EPC Natural Products Co., Ltd.

  公开号：US11154079B2

  公开（公告）日：2021-10-26

  The invention describes products, uses thereof, compositions thereof, and methods to prepare products formed from Maillard reaction products from a sugar donor and/or sweet tea extracts, stevia extracts, swingle (mogroside) extracts, one or more sweet tea extract components, one or more steviol glycosides, one or more mogrosides, one or more glycosylated sweet tea glycosides, one or more glycosylated steviol glycosides or one or more glycosylated mogrosides and an amine donor/reactant.

  本发明描述了由糖供体和/或甜茶提取物、甜叶菊提取物、秋茄（mogroside）提取物、一种或多种甜茶提取物成分、一种或多种甜菊醇苷、一种或多种mogrosides、一种或多种糖基化甜茶苷、一种或多种糖基化甜菊醇苷或一种或多种糖基化mogrosides和胺供体/反应物的Maillard反应产物形成的产品、其用途、其组合物和制备方法。
• TOBACCO TREATMENT
  申请人：British American Tobacco (Investments) Ltd

  公开号：EP3062640B1

  公开（公告）日：2019-07-24