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相关概念视频

Organic Compounds03:02

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Structures of Aldehydes and Ketones01:04

Structures of Aldehydes and Ketones

Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a strong-smelling ingredient in nail polish removers, all belong to a class of carbonyl compounds called aldehydes and ketones (Figure 1). Although both aldehydes and ketones contain the characteristic carbonyl (C=O) bond, their chemical structures vary with respect to the groups directly attached to the carbonyl carbon.
In aldehydes (Figures 1a and 1b), the carbonyl...

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相关实验视频

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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合成的 (-) - 吗啡.

Douglass F Taber1, Timothy D Neubert, Arnold L Rheingold

  • 1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu

Journal of the American Chemical Society
|October 17, 2002
PubMed
概括

这项研究详细介绍了一种新的 (-) - 吗啡合成方法. 基托阿尔代的关键双内分子循环使得四环中间体的高效构建成为可能,从而导致目标分子.

科学领域:

  • 有机化学 有机化学
  • 合成化学 合成化学
  • 药用化学 医学化学

背景情况:

  • (-) 吗啡是一种具有复杂立体化学的关键阿片类止痛药.
  • 有效和立体选择性的合成路径对吗啡具有重大兴趣.
  • 以前的合成通常涉及许多步骤和具有挑战性的立体化学控制.

研究的目的:

  • 开发一种新且高效的 (-) - 吗啡合成策略.
  • 使用关键循环反应建立立体选择性路径.
  • 为了证明二聚体和反聚体纯的中间体的合成.

主要方法:

  • 准备一种二聚体质纯β-四隆基.
  • 内分子基烯C-H插入和随后的水解.
  • 基托化物的双内分子循环形成一个四环中间体.
  • 将四环中间体转化为 (-) - 吗啡的多步转化.

主要成果:

  • 成功合成二聚体纯β-四隆基 4.成功合成二聚体纯β-四隆基
  • 通过C-H插入和水解生成基纯环素15.
  • 有效的双内分子循环生成四环中间体 20.

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  • 介质20的转化为 (-) - 吗啡 1.
  • 结论:

    • 报告的合成途径为 (-) - 吗啡提供了一条有效的途径.
    • 关键的双内分子循环是构建复杂的多环系统的强大工具.
    • 这种方法提供了一个潜在的可扩展的方法来访问morphinans.