(+/-)-N-allyl-5-(2-thienoyl)-2-pyrrolidinone | 1374311-48-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-N-allyl-5-(2-thienoyl)-2-pyrrolidinone
• CAS: 1374311-48-4
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: HYYYRWRXHIMWBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-N-allyl-5-(2-thienoyl)-2-pyrrolidinone 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0~40.0 ℃ 、482.64 kPa 条件下， 反应 25.0h， 生成 (+/-)-(8S,8aR)-8-hydroxy-8-(2-thienyl)-hexahydroindolizin-3(5H)-one
  参考文献：
  名称：

  Application of the intramolecular PIFA-mediated amidation of alkynes to the synthesis of substituted indolizidinones

  摘要：

  The construction of the title compounds has been achieved from properly substituted linear alkynylamides through the suitable combination of two key cyclization steps. First, an intramolecular PIFA-mediated alkyne amidation protocol leads to the creation of the pyrrolidinone nucleus, which under proper manipulation of the generated keto carbonyl group permits the assembling of the indolizidinone skeleton by the introduction of a subsequent ring closing olefin metathesis step. Finally, its transformation into a series of substituted mono- and trihydroxylated indolizidinone derivatives is achieved by manipulation of the remaining unsaturated fragment under hydrogenation and dihydroxylation conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.033
• 作为产物：
  描述：

  N-allyl-4-pentynamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 74.0h， 生成 (+/-)-N-allyl-5-(2-thienoyl)-2-pyrrolidinone
  参考文献：
  名称：

  Application of the intramolecular PIFA-mediated amidation of alkynes to the synthesis of substituted indolizidinones

  摘要：

  The construction of the title compounds has been achieved from properly substituted linear alkynylamides through the suitable combination of two key cyclization steps. First, an intramolecular PIFA-mediated alkyne amidation protocol leads to the creation of the pyrrolidinone nucleus, which under proper manipulation of the generated keto carbonyl group permits the assembling of the indolizidinone skeleton by the introduction of a subsequent ring closing olefin metathesis step. Finally, its transformation into a series of substituted mono- and trihydroxylated indolizidinone derivatives is achieved by manipulation of the remaining unsaturated fragment under hydrogenation and dihydroxylation conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.033