3-Acetyl-6-chloro-2-methylsulfanyl-1H-quinolin-4-one | 548929-92-6

• 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: 3-Acetyl-6-chloro-2-methylsulfanyl-1H-quinolin-4-one
• CAS: 548929-92-6
• 化学式: C₁₂H₁₀ClNO₂S
• 分子量: 267.736
• InChiKey: XGTZWWOXCPCBPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 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：
  71.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Acetyl-6-chloro-2-methylsulfanyl-1H-quinolin-4-one 在 双氧水 、 溶剂黄146 作用下， 反应 24.0h， 以88%的产率得到6-chloro-2-methylsulfinyl-3-acetyl-1H-quinolin-4-one
  参考文献：
  名称：

  合成高度官能化的2-和4-氨基喹啉衍生物的方法

  摘要：

  一种用于2-和4-氨基喹啉衍生物的合成方法，这需要-2-甲硫基- 3-酰基-1的2-或4-取代基的选择性激活的优点ħ -喹啉-4-酮1，已经研制成功。由于先前已描述了由4-喹啉酮1形成3-氨基喹啉酮的方法，因此新方法包括从普通的4-喹啉酮开始选择性合成三种异构的2-，3-和4-氨基喹啉衍生物的通用方法。1。

  DOI：

  10.1016/j.tet.2008.05.014
• 作为产物：
  描述：

  ethyl 2-acetyl-3,3-bis(methylthio)acrylate 、 对氯苯胺 以 乙醇 为溶剂， 反应 3.0h， 以66%的产率得到3-Acetyl-6-chloro-2-methylsulfanyl-1H-quinolin-4-one
  参考文献：
  名称：

  Synthesis of new polysubstituted (pyrazoles, pyrimidines and quinolines) five and six-membered heterocycles: reaction of α,α-dioxoketene dithioacetals with nucleophiles

  摘要：

  A novel synthesis of polysubstituted pyrazoles 3a-d, pyrimidines 4a-f and quinolines 5a-c via the reaction of alpha,alpha-oxoketene dithioacetals 2a-c with hydrazine hydrate, malonohydrazide, urea, thiourea and aniline is reported and the synthetic potential of the method is demonstrated. The structure of the new compounds was established upon their elemental analysis, IR, H-1 NMR and C-13 NMR. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.003

文献信息

• Isothiazole Ring Formation with Substituted 2-Alkylthio-3-acyl-4-quinolinone Using<i>O-</i>(Mesitylenesulfonyl)hydroxylamine (MSH)
  作者：Chwang Siek Pak、Jong Hee Choi、Eun Bok Choi

  DOI：10.1055/s-2003-36802

  日期：——

  Isothiazole ring skeleton was formed by the treatment of substituted 2-alkylthio-3-acyl-4-quinolinone with O-(mesitylenesulfonyl)hydroxylamine(MSH). A mixture of alkyl transferred 3-methyl-9-alkyl-4,9-dihydroisothiazolo[5,4-b]quinolin-4-one as a major product and dealkylated 3-methyl-4,9-dihydroisothiazolo[5,4-b]quinolin-4-one as a minor product was obtained from unsubstituted 2-alkylthio-3-acyl-4-quinolinone in the presence of K2CO3. When 2 equivalents of MSH were used in the absence of K2CO3 only dealkylated product was obtained in quantitative yield.

  O-(mesitylenesulfonyl)hydroxylamine(MSH) 处理取代的 2-烷硫基-3-乙酰基-4-喹啉酮，形成异噻唑环骨架。 在 K2CO3 的存在下，从未取代的 2-烷硫基-3-乙酰基-4-喹啉酮中得到了以烷基转移的 3-甲基-9-烷基-4,9-二氢异噻唑并[5,4-b]喹啉-4-酮为主要产物，以脱烷基的 3-甲基-4,9-二氢异噻唑并[5,4-b]喹啉-4-酮为次要产物的混合物。在没有 K2CO3 的情况下，使用 2 个等量的 MSH 时，只能得到定量的脱烷基产物。
• Synthesis of new polysubstituted (pyrazoles, pyrimidines and quinolines) five and six-membered heterocycles: reaction of α,α-dioxoketene dithioacetals with nucleophiles
  作者：M.A. Ebraheem、K.M. Lokanatha Rai、N.U. Kudva.N、A.S. Bahjat

  DOI：10.1016/j.tetlet.2010.04.003

  日期：2010.7

  A novel synthesis of polysubstituted pyrazoles 3a-d, pyrimidines 4a-f and quinolines 5a-c via the reaction of alpha,alpha-oxoketene dithioacetals 2a-c with hydrazine hydrate, malonohydrazide, urea, thiourea and aniline is reported and the synthetic potential of the method is demonstrated. The structure of the new compounds was established upon their elemental analysis, IR, H-1 NMR and C-13 NMR. (C) 2010 Elsevier Ltd. All rights reserved.
• A methodology for the synthesis of highly functionalized 2- and 4-aminoquinoline derivatives
  作者：Bo Hyun Hwang、Sung Hee Park、Eun Bok Choi、Chwang Siek Pak、Hyeon Kyu Lee

  DOI：10.1016/j.tet.2008.05.014

  日期：2008.7

  for the synthesis of 2- and 4-aminoquinoline derivatives, which takes advantage of selective activation of 2- or 4-substituent of 2-methylsulfanyl-3-acyl-1H-quinolin-4-one 1, has been developed. Since a procedure for formation of 3-aminoquinolinones from the 4-quinolinone 1 was described previously, the new methodology comprises a general methodology for the selective syntheses of three isomeric 2-, 3-

  一种用于2-和4-氨基喹啉衍生物的合成方法，这需要-2-甲硫基- 3-酰基-1的2-或4-取代基的选择性激活的优点ħ -喹啉-4-酮1，已经研制成功。由于先前已描述了由4-喹啉酮1形成3-氨基喹啉酮的方法，因此新方法包括从普通的4-喹啉酮开始选择性合成三种异构的2-，3-和4-氨基喹啉衍生物的通用方法。1。