4-methyl-2-(1,3,5-trioxan-2-yl)quinoline | 40105-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-methyl-2-(1,3,5-trioxan-2-yl)quinoline
• CAS: 40105-26-8
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: FJSGGYWXPWKGDU-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  384.2±37.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(1,3,5-trioxan-2-yl)quinoline 在 硫酸 作用下， 反应 5.0h， 以0.38 g的产率得到4-甲基喹啉-2-甲醛
  参考文献：
  名称：

  Synthesis and anti-norovirus activity of pyranobenzopyrone compounds

  摘要：

  During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 mu M and TD50 values of >200 and 96.4 mu M, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.084
• 作为产物：
  描述：

  三聚甲醛 、 4-甲基喹啉 在 盐酸 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以36%的产率得到4-methyl-2-(1,3,5-trioxan-2-yl)quinoline
  参考文献：
  名称：

  绿色氧化剂H 2 O 2作为氢原子转移试剂，用于可见光介导的Minisci反应†

  摘要：

  通过自由基途径实现了杂芳烃和脂肪族CH组分的无金属氧化偶联的可见光介导的“绿色”方案。这种交叉脱氢偶联方法具有广泛的底物特征。绿色氧化剂H 2 O 2用作氢原子转移试剂，对环境无害，成本低廉且原子经济。

  DOI：

  10.1039/c9nj03106e

文献信息

• Visible Light-Promoted Aliphatic C–H Arylation Using Selectfluor as a Hydrogen Atom Transfer Reagent
  作者：Hong Zhao、Jian Jin

  DOI：10.1021/acs.orglett.9b01635

  日期：2019.8.16

  A mild, practical method for direct arylation of unactivated C(sp3)–H bonds with heteroarenes has been achieved via photochemistry. Selectfluor is used as a hydrogen atom transfer reagent under visible light irradiation. A diverse range of chemical feedstocks, such as alkanes, ketones, esters, and ethers, and complex molecules readily undergo intermolecular C(sp3)–C(sp2) bond formation. Moreover, a

  通过光化学已经实现了一种温和的，实用的方法，用于将未激活的C（sp 3）–H键与杂芳烃直接芳基化。Selectfluor在可见光照射下用作氢原子转移试剂。各种各样的化学原料，例如烷烃，酮，酯和醚，以及复杂的分子容易形成分子间的C（sp 3）–C（sp 2）键。此外，可通过此处介绍的方案有效地烷基化各种杂芳烃，包括药学上有用的支架。
• Cross-Dehydrogenative Coupling of Strong C(sp³)–H with <i>N</i>-Heteroarenes through Visible-Light-Induced Energy Transfer
  作者：Haitao Tian、Hui Yang、Chao Tian、Guanghui An、Guangming Li

  DOI：10.1021/acs.orglett.0c02912

  日期：2020.10.2

  The sustainable cross-dehydrogenative coupling of strong C(sp(3))-H with N-heteroarenes has been developed using an efficient organic photocatalyst. It features atomic- and step-economy, and acid-free conditions. Mechanism studies suggest a previous elusive energy transfer pathway from photocatalyst to N-heteroarenes and oxidants.
• Homolytic aromatic substitution: A simple route to the aldehydes of heteroaromatic bases
  作者：G.P. Gardini

  DOI：10.1016/s0040-4039(01)94251-0

  日期：1972.1
• Citterio, Attilio; Casucci, Domenico; Gentile, Anna, Gazzetta Chimica Italiana, 1985, vol. 115, # 6, p. 319 - 324
  作者：Citterio, Attilio、Casucci, Domenico、Gentile, Anna、Serravalle, Marco、Ventura, Susanna

  DOI：——

  日期：——
• A general, selective, and convenient procedure of homolytic formylation of heteroaromatic bases
  作者：Claudio Giordano、Francesco Minisci、Elena Vismara、Silvio Levi

  DOI：10.1021/jo00354a026

  日期：1986.2