cis-3-(3-quinolyl)-2-propen-1-ol | 314050-18-5

• 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: cis-3-(3-quinolyl)-2-propen-1-ol
• 英文别名: (Z)-3-quinolin-3-ylprop-2-en-1-ol
• CAS: 314050-18-5
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: POWFQRDLWMFWPX-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-3-(3-quinolyl)-2-propen-1-ol 在 tris(dibenzylideneacetone)dipalladium (0) sodium hydroxide 、 n-Bu₄HSO₄ 、 1,4-双(二苯基膦)丁烷 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Allylation of Erythromycin Derivatives:  Introduction of Allyl Substituents into Highly Hindered Alcohols

  摘要：

  Functionalized erythromycin 9-oxime derivatives are 6-O-allylated under mild conditions using substituted allyl tert-butyl carbonates under palladium(0) catalysis. This allylation works well where traditional ether-forming protocols function poorly. Allyl tert-butyl carbonates provide higher yields in this reaction than lesser substituted carbonates such as ethyl or isopropyl. Aryl-substituted allyl carbonates or carbamates may be employed as well and, when used, produce trans-olefinic products.

  DOI：

  10.1021/jo034883z
• 作为产物：
  描述：

  3-(3-quinolinyl)-2-propyn-1-ol 在 Lindlar's catalyst 3,6-二硫杂-1,8-辛二醇 、 氢气 作用下， 以 乙醇 为溶剂， 19.0 ℃ 、2.07 kPa 条件下， 反应 25.0h， 以50.0 g的产率得到cis-3-(3-quinolyl)-2-propen-1-ol
  参考文献：
  名称：

  Allylation of Erythromycin Derivatives:  Introduction of Allyl Substituents into Highly Hindered Alcohols

  摘要：

  Functionalized erythromycin 9-oxime derivatives are 6-O-allylated under mild conditions using substituted allyl tert-butyl carbonates under palladium(0) catalysis. This allylation works well where traditional ether-forming protocols function poorly. Allyl tert-butyl carbonates provide higher yields in this reaction than lesser substituted carbonates such as ethyl or isopropyl. Aryl-substituted allyl carbonates or carbamates may be employed as well and, when used, produce trans-olefinic products.

  DOI：

  10.1021/jo034883z

文献信息

• Preparation of quinoline-substituted carbonate and carbamate derivatives
  申请人：——

  公开号：US20020013468A1

  公开（公告）日：2002-01-31

  The invention relates to a process for preparing quinoline-substituted carbonate and carbamate compounds, which are important intermediates in the synthesis of 6-O-substituted macrolide antibiotics. The process employs metal-catalyzed coupling reactions to provide a carbonate or carbamate of formula (I) or (II) or a substrate that can be reduced to obtain the same.

  该发明涉及一种制备喹啉取代碳酸酯和氨基甲酸酯化合物的过程，这些化合物是合成6-O取代大环内酯抗生素的重要中间体。该过程利用金属催化的偶联反应来提供式(I)或(II)的碳酸酯或氨基甲酸酯，或者可以还原得到相同化合物的底物。
• [EN] PROCESS FOR PREPARING 6-O-SUBSITUTED ERYTHROMYCIN DERIVATIVES<br/>[FR] METHODE DE PREPARATION DE DERIVES D'ERYTHROMYCINE SUBSTITUES EN 6-O
  申请人：ABBOTT LAB

  公开号：WO2000078773A2

  公开（公告）日：2000-12-28

  In one aspect, the invention relates to a process for preparing 6-O-substituted erythromycin derivatives comprising reacting 2'-substituted and optionally 4'-substituted 9-oxime erythromycin derivatives with an alkylating agent in the presence of a palladium catalyst and phosphine. In another aspect, the invention relates to processes for preparing 6-O-substituted erythromycin ketolides using the palladium-catalyzed alkylation reaction.

  在一个方面，本发明涉及一种制备6-O取代红霉素衍生物的过程，包括在钯催化剂和膦的存在下，将2'-取代和可选的4'-取代的9-肟红霉素衍生物与烷基化试剂反应。在另一个方面，本发明涉及使用钯催化烷基化反应制备6-O取代红霉素酮环内酯的过程。
• [EN] PREPARATION OF QUINOLINE-SUBSTITUTED CARBONATE AND CARBAMATE DERIVATIVES<br/>[FR] PREPARATION DE DERIVES DE CARBONATE ET DE CARBAMATE A SUBSTITUTION QUINOLINE
  申请人：ABBOTT LAB

  公开号：WO2001000582A1

  公开（公告）日：2001-01-04

  The invention relates to a process for preparing quinoline-substituted carbonate and carbamate compounds, which are important intermediates in the synthesis of 6-O-substituted macrolide antibiotics. The process employs metal-catalyzed coupling reactions to provide a carbonate or carbamate of formula (I) or (II) or a substrate that can be reduced to obtain the same.

  本发明涉及一种制备喹啉取代碳酸酯和氨基甲酸酯化合物的方法，这些化合物是合成6-O-取代大环内酯类抗生素的重要中间体。该方法采用金属催化偶联反应，以提供式（I）或（II）的碳酸酯或氨基甲酸酯，或者可以还原得到相同的底物。
• Process for preparing 6-o-substituted erythromycin derivatives
  申请人：Abbott Laboratories

  公开号：US06437106B1

  公开（公告）日：2002-08-20

  In one aspect, the invention relates to a process for preparing 6-O-substituted erythromycin derivatives comprising reacting 2′-substituted and optionally 4″-substituted 9-oxime erythromycin derivatives with an alkylating agent in the presence of a palladium catalyst and phosphine. In another aspect, the invention relates to processes for preparing 6-O-substituted erythromycin ketolides using the palladium-catalyzed alkylation reaction.

  在一个方面，本发明涉及一种制备6-O取代红霉素衍生物的方法，包括在钯催化剂和膦的存在下，将2'-取代和可选的4''-取代9-肟基红霉素衍生物与烷基化试剂反应。在另一个方面，本发明涉及使用钯催化烷基化反应制备6-O取代红霉素酮类的方法。
• Preparation of substituted carbonate and carbamate derivatives
  申请人：Abbott Laboratories

  公开号：EP2409964A2

  公开（公告）日：2012-01-25

  The invention relates to a process for preparing carbonate and carbamate compounds, which are important intermediates in the synthesis of 6-O-substituted macrolide antibiotics. The process employs metal-catalyzed coupling reactions to provide a carbonate or carbamate of formula (I) or a substrate that can be reduced to obtain the same.         R1-CH=CHCH2OC(O)-X-R2     (I)

  本发明涉及一种制备碳酸盐和氨基甲酸酯化合物的工艺，这些化合物是合成 6-O-取代大环内酯类抗生素的重要中间体。该工艺采用金属催化的偶联反应，提供式（I）的碳酸盐或氨基甲酸酯或可被还原以获得相同物质的底物。 R1-CH=CHCH2OC(O)-X-R2 (I)