N-acetonylisoquinolinium bromide | 39954-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-acetonylisoquinolinium bromide
• 英文别名: N-(2-oxopropyl)isoquinolinium bromide；2-acetonyl-isoquinolinium; bromide；2-Acetonyl-isochinolinium; Bromid；1-isoquinolin-2-ium-2-ylpropan-2-one;bromide
• CAS: 39954-56-8
• 化学式: Br*C₁₂H₁₂NO
• 分子量: 266.137
• InChiKey: GGQFYNIXLDUOLC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.28
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-acetonylisoquinolinium bromide 在 水 、 potassium carbonate 作用下， 生成 2-acetonyl-isoquinolinium; betaine
  参考文献：
  名称：

  Kroehnke, Chemische Berichte, 1935, vol. 68, p. 1177,1189

  摘要：

  DOI：
• 作为产物：
  描述：

  异喹啉 、 溴丙酮 在 乙醚 作用下， 生成 N-acetonylisoquinolinium bromide
  参考文献：
  名称：

  Kroehnke, Chemische Berichte, 1935, vol. 68, p. 1177,1189

  摘要：

  DOI：

文献信息

• A Convenient Synthesis Of 1-Acyl Indolizines by 1,3-Dipolar Cycloaddition Reactions of Pyridinium Ylides and α,β-Unsaturated Aldehydes or Ketones in the Presence of Tetrakis-Pyridine Cobalt Dichromate
  作者：Xuechun Zhang、Weili Cao、Xudong Wei、Hongwen Hu

  DOI：10.1080/00397919708006070

  日期：1997.4

  Abstract In the presence of tetrakispyridine cobalt dichromate (CoPy4(HCrO4)2), pyridinium ylides and α,β-unsaturated aldehydes or ketones undergo 1,3-dipolar cycloaddition reactions followed by in situ aromatization to give 1-acyl substituted indolizines in moderate to good yields.

  摘要 在四吡啶重铬酸钴 (CoPy4(HCrO4)2) 存在下，吡啶鎓叶立德和 α,β-不饱和醛或酮发生 1,3-偶极环加成反应，然后原位芳构化，得到 1-酰基取代的吲哚茚。良好的收益。
• 5-(Arylmethylidene)-2,4,6-pyrimidine-2,4,6(1H,3H,5H)-triones in reaction with p-phenacyl- and p-acetonylisoquinolinium bromides
  作者：A. G. Tyrkov、S. B. Nosachev、T. S. Vladimirova

  DOI：10.1134/s1070428016050274

  日期：2016.5

  Information on chemical reactions of azomethine ylides generated from N-phenacyland N-acetonylisoquinolinium bromides is scarce. It is only known that 1-nitro-2-phenylethene reacts with N-[2-methyl-5(methoxycarbonyl)furan-3-yl]methylisoquinolinium bromide to give a product of 1,3-dipolar cycloaddition, 1-nitro-2-phenyl-2,3-dihydrobenzo[g]indolizine, and the reaction of 1-nitro-2-phenyl-1-cyanoethene

  N-phenacyland N-acetonylisoquinolinium bromides 产生的偶氮甲碱叶立德的化学反应信息很少。仅知道 1-nitro-2-phenylethene 与 N-[2-methyl-5(methoxycarbonyl)furan-3-yl]methylisoquinolinium bromide 反应生成 1,3-偶极环加成产物 1-nitro-2 -苯基-2,3-二氢苯并[g]中氮茚，1-nitro-2-phenyl-1-cyanoethene 与 Nphenacylor N-acetonylisoquinolinium bromides 反应生成 1-nitro-2-phenyl-1,2 ,3,10b-四氢吡咯并[2,1-а]异喹啉 [1, 2]。
• Synthesis of Stable N–H Imines with a Benzo[7,8]indolizine Core and Benzo[7,8]indolizino[1,2-<i>c</i>]quinolines via Copper-Catalyzed Annulation of α,β-Unsaturated <i>O</i>-Acyl Ketoximes with Isoquinolinium <i>N</i>-Ylides
  作者：Chun-Bao Miao、Xiao-Qi Qiang、Xiaoli Xu、Xiao-Qing Song、Su-Qing Zhou、Xinyu Lyu、Hai-Tao Yang

  DOI：10.1021/acs.orglett.2c01386

  日期：2022.6.3

  A copper-catalyzed annulation of α,β-unsaturated O-acyl ketoximes with isoquinolinium N-ylides has been developed for the concise synthesis of stable N–H imines with a benzo[7,8]indolizine core. When β-(2-bromoaryl)-α,β-unsaturated O-acyl ketoximes are used as the starting materials, a cascade cyclization occurs to afford the benzo[7,8]indolizino[1,2-c]quinolines.

  已经开发了一种铜催化的α,β-不饱和O-酰基酮肟与异喹啉N-叶立德的环化反应，用于简明地合成具有苯并 [7,8] 中氮茚核的稳定 N-H 亚胺。当β-(2-溴芳基) -α,β-不饱和O-酰基酮肟作为起始原料时，发生级联环化反应得到苯并[7,8]中氮茚基[1,2- c ]喹啉。
• Fine tuning of the pH-dependent drug release rate from polyHPMA-ellipticinium conjugates
  作者：Ondřej Sedláček、Martin Studenovský、David Větvička、Karel Ulbrich、Martin Hrubý

  DOI：10.1016/j.bmc.2013.07.038

  日期：2013.9

  Polymer conjugates of anticancer drugs have shown high potential for assisting in cancer treatments. The pH-labile spacers allow site-specific triggered release of the drugs. We synthesized and characterized model drug conjugates with hydrazide bond-containing poly[N-(2-hydroxypropyl)methacrylamide] differing in the chemical surrounding of the hydrazone bond-containing spacer to find structure-drug release rate relationships. The conjugate selected for further studies shows negligible drug release in a pH 7.4 buffer but released 50% of the ellipticinium drug within 24 h in a pH 5.0 phosphate saline buffer. The ellipticinium drug retained the antiproliferative activity of the ellipticine. (C) 2013 Elsevier Ltd. All rights reserved.
• Substituted 1-nitro-2-phenylethenes in reaction with N-phenacyl- and N-acetonylisoquinolinium bromides
  作者：S. B. Nosachev、K. A. Del’netskaya、N. A. Solov’ev、A. G. Tyrkov

  DOI：10.1134/s1070428010090319

  日期：2010.9