3-Cyan-1-phenacylpyridiniumbromid | 25357-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Cyan-1-phenacylpyridiniumbromid
• 英文别名: N-Phenacyl-3-cyanopyridiniumbromid；m-Cyan-N-phenacylpyridiniumbromid；3-Cyano-1-(2-oxo-2-phenylethyl)pyridin-1-ium bromide；1-phenacylpyridin-1-ium-3-carbonitrile;bromide
• CAS: 25357-46-4
• 化学式: Br*C₁₄H₁₁N₂O
• 分子量: 303.158
• InChiKey: MEIMXLIQILLRLJ-UHFFFAOYSA-M

物化性质

• 熔点：
  198 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.27
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Cyan-1-phenacylpyridiniumbromid 在 potassium carbonate 、 三乙胺 、 2,2-difluorovinyl tosylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60%的产率得到3-benzoyl-2-phenyl-indolizine-6-carbonitrile
  参考文献：
  名称：

  Synthesis of monofluorinated indolizines and their derivatives by the 1,3-dipolar reaction of N-ylides with fluorinated vinyl tosylates

  摘要：

  Monofluorinated indolizines 4, benzo[d]indolizines 7 and 4H-pyrrolo[1,2-a]benzimidazoles 8 were synthesized in moderate yields by 1,3-dipolar reaction between fluorinated vinyl tosylates 2a and N-ylides of pyridinium, isoquinolinium and benzimidazolinium, generated in situ from their halides salts. When the same N-ylides were allowed to react with 2,3,3-trifluoro-1-propenyl tosylate 2b, the unexpected product formylated indolizines and their derivatives 9 were obtained. The reaction mechanism is also proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.012
• 作为产物：
  描述：

  3-氰基吡啶 、 2-溴苯乙酮 以 neat (no solvent) 为溶剂， 反应 4.0h， 生成 3-Cyan-1-phenacylpyridiniumbromid
  参考文献：
  名称：

  Copper acetate monohydrate: a cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes

  摘要：

  我们报道了一种高度实用的、一步合成多取代吲哚嗪的方法，该方法使用α-卤代羰基化合物、吡啶和缺电子烯烃，在醋酸铜一水合物和醋酸钠的DMF溶液中进行。在标准反应条件下，各种功能团（包括醛）都能耐受。我们提供了36个例子，吲哚嗪的产率从中等到高。此外，通过这种方法还能在克级规模上制备多取代吲哚嗪。

  DOI：

  10.1039/c2ra21213g

文献信息

• Copper acetate monohydrate: a cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes
  作者：Huayou Hu、Junjun Feng、Yulan Zhu、Ning Gu、Yuhe Kan

  DOI：10.1039/c2ra21213g

  日期：——

  We report a highly practical one-pot method for synthesizing multi-substituted indolizines from α-halide carbonyl compounds, pyridines and electron deficient alkenes in the presence of copper acetate monohydrate and sodium acetate in DMF. A variety of function groups are tolerable in standard reaction conditions, including aldehyde. 36 examples were presented. The yield of indolizine was from moderate to high. Furthermore, multi-substituted indolizines can be prepared at gram scale by this method.

  我们报道了一种高度实用的、一步合成多取代吲哚嗪的方法，该方法使用α-卤代羰基化合物、吡啶和缺电子烯烃，在醋酸铜一水合物和醋酸钠的DMF溶液中进行。在标准反应条件下，各种功能团（包括醛）都能耐受。我们提供了36个例子，吲哚嗪的产率从中等到高。此外，通过这种方法还能在克级规模上制备多取代吲哚嗪。
• Kinetics and Mechanism of the Pyridinolysis of Phenacyl Bromides in Acetonitrile
  作者：Han Joong Koh、Kwang Lae Han、Hai Whang Lee、Ikchoon Lee

  DOI：10.1021/jo000411y

  日期：2000.7.1

  studies of the reactions of substituted phenacyl bromides (YC6H4COCH2Br) with pyridines (XC5H4N) are carried out in acetonitrile at 45.0 degrees C. A biphasic Bronsted plot is obtained with a change in slope from a large (betaX approximately equals 0.65-0.80) to a small (betaX approximately 0.36-0.40) value at pKa = 3.2-3.6, which can be attributed to a change in the rate-determining step from breakdown

  在45.0摄氏度下于乙腈中进行了取代的苯甲酰溴（YC6H4COCH2Br）与吡啶（XC5H4N）反应的动力学研究。获得了双相布朗斯台德图，其斜率从大（βX约等于0.65-0.80）变化为pKa = 3.2-3.6时有一个很小的值（betaX大约为0.36-0.40），这可以归因于随着吡啶亲核试剂的碱度增加，从分解到反应路径中四面体中间体形成的速率确定步骤发生变化。吡啶比苯胺具有更快的速率以及交叉相互作用常数rhyXY从大的正（rhoXY = +1.4）到小的正的（rhoXY大约+0.1）值的变化支持了该机制。Hammett rhoX的大小很大（= -5.5至-6。9）具有吸电子取代基的吡啶值和pi受体p-CH3CO和p-CN的正偏差与吡啶离子形成平衡的值非常相似。激活参数也符合所提出的机制。
• Cu-catalyzed transannulation reaction of pyridotriazoles: general access to fused polycyclic indolizines
  作者：Yi Shi、Vladimir Gevorgyan

  DOI：10.1039/c5cc07598j

  日期：——

  AN EFFICIENT INTRAMOLECULAR TRANSANNULATION REACTION OF PYRIDOTRIAZOLES WITH INTERNAL ALKYNES EN ROUTE TO VARIOUS FUSED POLYCYCLIC INDOLIZINES HAS BEEN DEVELOPED. FOR THE FIRST TIME IT WAS SHOWN THAT IN ADDITION...

  已开发了带有内部链烯基的吡咯并三唑与多种熔融多聚吲哚嗪有效的分子内跨膜反应。第一次显示它是附加的...
• Phalaenopsis orchid plant named ‘Joyride’
  申请人：Floricultura

  公开号：USPP029153P3

  公开（公告）日：2018-03-27

  A new and distinct Phalaenopsis plant named ‘Joyride’ particularly characterized by flowers which are purple/violet with thin white edges and a purple labellum; plants which may be propagated economically and uniformly using tissue culture; plants which produce more than one inflorescence; long and sturdy inflorescences; and relatively short, dark-green foliage.

  一种新的独特的蝴蝶兰植物，名为“Joyride”，其特点是花朵呈紫色/紫罗兰色，边缘带有白色，唇瓣为紫色；该植物可以通过组织培养经济、统一地繁殖；该植物可以产生多个花序；花序长而坚固；叶片相对较短，呈深绿色。
• Shunmugasundaram, A.; Balakumar, S., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1985, vol. 24, # 9, p. 775 - 777
  作者：Shunmugasundaram, A.、Balakumar, S.

  DOI：——

  日期：——