1-(甲氧羰基)-2-吡咯啉 | 185958-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 1-(甲氧羰基)-2-吡咯啉
• 英文名称: N-Propionyl-2-pyrroline
• 英文别名: 1-(2,3-Dihydropyrrol-1-yl)propan-1-one
• CAS: 185958-72-9
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: DULZYNQGXJKFLM-UHFFFAOYSA-N

物化性质

• 沸点：
  241.6±10.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(甲氧羰基)-2-吡咯啉 在 三甲基氯硅烷 、 lithium diisopropyl amide 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-hexyl-6,7-dihydro-3-methyl-4H-pyrrole[2,1-b][1,3]oxazine-4,8(8aH)-dione 8-oxime
  参考文献：
  名称：

  Synthesis of racemic brevioxime and related analogues

  摘要：

  Racemic brevioxime and the related model compounds have been synthesised starting from N-propionyl-2-pyrroline by intramolecular cyclisation of a beta -ketoamide using nitrosyl chloride. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00835-3
• 作为产物：
  描述：

  3,4-二氢-2H-吡咯 、 丙酰氯 在 三乙胺 作用下， 生成 1-(甲氧羰基)-2-吡咯啉
  参考文献：
  名称：

  A Rapid Synthesis of Racemic Brevioxime

  摘要：

  由N-丙酰基-2-吡咯啉出发，通过使用亚硝酰氯的β-酮酰胺分子内环化反应，已合成了外消旋的短环昔脒。

  DOI：

  10.1055/s-2001-10769

文献信息

• Lewis acid-catalyzed reaction between tertiary enamides and imines of salicylaldehydes: expedient synthesis of novel 4-chromanamine derivatives
  作者：Ling He、Han-Bin Liu、Liang Zhao、De-Xian Wang、Mei-Xiang Wang

  DOI：10.1016/j.tet.2014.12.050

  日期：2015.1

  catalytic amount of Zn(OTf)2 in DCE at ambient temperature, a number of tertiary enamides underwent highly efficient reaction with imines of salicylaldehydes to afford diverse functionalized 4-chromanamine derivatives in high yields. The reaction proceeds most probably through an enaminic addition of tertiary enamides to imine functionality followed by the intramolecular interception of the resulting iminium

  在环境温度下，在DCE中催化量的Zn（OTf）2存在下，许多叔酰胺与水杨醛的亚胺进行高效反应，从而以高收率提供了多种官能化的4-chromanamine衍生物。该反应最有可能通过将叔酰胺类烯胺类加成到亚胺官能团上，然后通过酚羟基将所得的亚胺中间体分子内截获来进行。合成也实际上是通过从水杨醛，对硝基苯胺和叔烯酰胺开始的三组分反应来进行的。
• PYRAZOLOPYRIMIDINE JAK INHIBITOR COMPOUNDS AND METHODS
  申请人：Genentech, Inc.

  公开号：US20150152117A1

  公开（公告）日：2015-06-04

  A compound of Formula I, enantiomers, diasteriomers, tautomers or pharmaceutically acceptable salts thereof, wherein R 1 , R 2 and R 3 are defined herein, are useful as inhibitors of one or more Janus kinases. A pharmaceutical composition that includes a compound of Formula I and a pharmaceutically acceptable carrier, adjuvant or vehicle, and methods of treating or lessening the severity of a disease or condition responsive to the inhibition of a Janus kinase activity in a patient are disclosed.

  公式I的化合物、对映异构体、二对映异构体、互变异构体或其药学上可接受的盐，其中R1、R2和R3如本文所定义，可用作一个或多个Janus激酶的抑制剂。本发明还涉及一种包括公式I化合物和药学上可接受的载体、辅料或溶剂的制药组合物，以及治疗或减轻患者对Janus激酶活性抑制有反应的疾病或病情的方法。
• Regioselective synthesis of pyrroloquinolines — Approaches to Martinelline
  作者：Mark Hadden、Paul J. Stevenson

  DOI：10.1016/s0040-4039(98)02569-6

  日期：1999.2

  Indium trichloride catalysed Diels-Alder reaction of imines derived from anilines with cyclic enamides regioselectively gave the biologically important pyrroloquinoline nucleus, with a cis ring junction, in moderate yield. Although the euo:endo selectivity was in most cases poor, these isomers are readily separated by flash chromatography. The functionality tolerated at both C2 and C7 should allow further elaboration to Martinelline (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis and reactivity of hexahydropyrroloquinolines
  作者：Mark Hadden、Mark Nieuwenhuyzen、Deirdre Potts、Paul J Stevenson、Norris Thompson

  DOI：10.1016/s0040-4020(01)00466-5

  日期：2001.6

  Formal [4+2] cycloaddition of cyclic enamides with imines derived from aromatic amines gave the 4-arylhexahydropyrroloquinoline skeleton in one step as mixtures of diastereoisomers. Aromatic imines derived from formaldehyde and methylglyoxalate also participated in this chemistry, with the latter favouring formation of the endo-cycloadduct. The cycloadducts derived from methylglyoxalate were unstable and fragmented to give highly substituted quinolines under both neutral and basic conditions. Imines derived from 3-cyanoacrolein also underwent cycloaddition and gave an advanced potential precursor to martinellic acid, albeit with poor diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Tietze; Thede, Synlett, 2000, # 10, p. 1470 - 1472
  作者：Tietze、Thede

  DOI：——

  日期：——