quinoline-8-carbodithioic acid methyl ester | 112307-45-6

• 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: quinoline-8-carbodithioic acid methyl ester
• 英文别名: Methyl quinoline-8-carbodithioate；methyl quinoline-8-carbodithioate
• CAS: 112307-45-6
• 化学式: C₁₁H₉NS₂
• 分子量: 219.331
• InChiKey: WVQVBYMJDGUYND-UHFFFAOYSA-N

物化性质

• 沸点：
  376.3±34.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  quinoline-8-carbodithioic acid methyl ester 在 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 8-[(R)-4,5-dihydro-4-phenyl-2-thiazolyl]quinoline
  参考文献：
  名称：

  Chiral thiazoline ligands: application in Pd-catalysed allylic substitution

  摘要：

  A series of thiazoline ligands, analogues of well-known oxazolines, easily prepared from chiral aminoalcohols, and appropriate dithioesters, was tested in the Pd-catalysed allylic substitution. A systematic comparison with the corresponding oxazolines (using literature data or our own tests) has been made for each case. Some important differences (between their catalytic activity and enantioselectivity) were noted for the two types of ligands, especially in the case of bis(thiazolines) and bis(oxazolines). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.048
• 作为产物：
  描述：

  8-溴甲基喹啉 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 potassium tert-butylate 、 四丙基溴化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 49.0h， 生成 quinoline-8-carbodithioic acid methyl ester
  参考文献：
  名称：

  Efficient New Protocol to Synthesize Aromatic and Heteroaromatic Dithioesters

  摘要：

  描述了一种高效、高产的合成取代芳香和杂芳香二硫酯的方法。该方法包括在碱性介质中（苯磺酰）甲基（杂）芳香衍生物与硫元素反应，随后进行烷基化。

  DOI：

  10.1055/s-2004-822311

文献信息

• Catalytic Enantioselective Additions of Indoles to Nitroalkenes
  作者：Madhu Ganesh、Daniel Seidel

  DOI：10.1021/ja8063292

  日期：2008.12.10

  A new design principle that provides access to more active thiourea catalysts is described. Highly enantioselective additions of indoles to nitroalkenes are reported using a new quinolinium thioamide catalyst.
• Efficient New Protocol to Synthesize Aromatic and Heteroaromatic Dithioesters
  作者：Serge Masson、Isabelle Abrunhosa、Mihaela Gulea

  DOI：10.1055/s-2004-822311

  日期：——

  A very efficient, high yielding procedure to synthesize substituted aromatic and heteroaromatic dithioesters is described. It involves the reaction between (phenylsulfonyl)methyl (hetero)aromatic derivatives and elemental sulfur in basic medium, followed by alkylation.

  描述了一种高效、高产的合成取代芳香和杂芳香二硫酯的方法。该方法包括在碱性介质中（苯磺酰）甲基（杂）芳香衍生物与硫元素反应，随后进行烷基化。
• Chiral thiazoline ligands: application in Pd-catalysed allylic substitution
  作者：Isabelle Abrunhosa、Lise Delain-Bioton、Annie-Claude Gaumont、Mihaela Gulea、Serge Masson

  DOI：10.1016/j.tet.2004.07.048

  日期：2004.10

  A series of thiazoline ligands, analogues of well-known oxazolines, easily prepared from chiral aminoalcohols, and appropriate dithioesters, was tested in the Pd-catalysed allylic substitution. A systematic comparison with the corresponding oxazolines (using literature data or our own tests) has been made for each case. Some important differences (between their catalytic activity and enantioselectivity) were noted for the two types of ligands, especially in the case of bis(thiazolines) and bis(oxazolines). (C) 2004 Elsevier Ltd. All rights reserved.