S-(3-butyl-6-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamate

• 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: S-(3-butyl-6-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamate
• 英文别名: S-[(3-butyl-6-chloro-2,4-dioxo-1H-quinolin-3-yl)] carbamothioate
• 化学式: C₁₄H₁₅ClN₂O₃S
• 分子量: 326.804
• InChiKey: BQCZOXHFHFLIKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-(3-butyl-6-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamate 在 phosphorus pentoxide 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以61%的产率得到3a-butyl-8-chloro[1,3]thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione
  参考文献：
  名称：

  Novel Tandem Hydration/Cyclodehydration of α-Thiocyanatoketones to 2-Oxo-3-thiazolines. Application to Thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione Synthesis

  摘要：

  Novel tandem hydration of alpha-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]-thiazolo[5,4-c]quinoline-2,4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1).

  DOI：

  10.1021/jo0493370
• 作为产物：
  描述：

  (3-butyl-6-chloro-2,4-dioxo-1H-quinolin-3-yl) thiocyanate 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.08h， 以18%的产率得到3a-butyl-8-chloro[1,3]thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione
  参考文献：
  名称：

  Novel Tandem Hydration/Cyclodehydration of α-Thiocyanatoketones to 2-Oxo-3-thiazolines. Application to Thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione Synthesis

  摘要：

  Novel tandem hydration of alpha-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]-thiazolo[5,4-c]quinoline-2,4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1).

  DOI：

  10.1021/jo0493370

文献信息

• Novel Tandem Hydration/Cyclodehydration of α-Thiocyanatoketones to 2-Oxo-3-thiazolines. Application to Thiazolo[5,4-<i>c</i>]quinoline-2,4(3a<i>H</i>,5<i>H</i>)-dione Synthesis
  作者：Antonín Klásek、Vladimír Mrkvička、Andrej Pevec、Janez Košmrlj

  DOI：10.1021/jo0493370

  日期：2004.8.1

  Novel tandem hydration of alpha-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]-thiazolo[5,4-c]quinoline-2,4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1).