N-allyl-2,4-dichlorobenzamide | 66898-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-allyl-2,4-dichlorobenzamide
• 英文别名: 2,4-dichloro-N-prop-2-enylbenzamide
• CAS: 66898-17-7
• 化学式: C₁₀H₉Cl₂NO
• mdl: MFCD01181350
• 分子量: 230.094
• InChiKey: GCEXIHJBPDKOON-UHFFFAOYSA-N

物化性质

• 沸点：
  331.7±42.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allyl-2,4-dichlorobenzamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以72%的产率得到5-(bromomethyl)-2-(2,4-dichlorophenyl)oxazole
  参考文献：
  名称：

  Catalyst-Free Intramolecular Oxidative Cyclization of N-Allylbenzamides: A New Route to 2,5-Substituted Oxazoles

  摘要：

  A catalyst-free intramolecular oxidative cyclization reaction of N-allylbenzamides has been developed to prepare 2,5-disubstituted oxazoles with good yields. This reaction gives an efficient synthetic strategy to form an oxazole nucleus directly from easily accessible substrates under temperate conditions.

  DOI：

  10.1021/ol302031z
• 作为产物：
  描述：

  2,4-二氯苯甲酸 、 丙烯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-allyl-2,4-dichlorobenzamide
  参考文献：
  名称：

  N-烯丙基甲酰胺的电化学氧化环化：有效合成卤代恶唑啉

  摘要：

  在此，我们报道了一种有效且可持续的N-烯丙基甲酰胺分子内电化学环化，用于合成各种卤代恶唑啉。该方法是在一个简单的未分隔的电池中进行的，使用锂卤盐作为氧化还原介质和卤素源。在室温下以中等至良好的产率构建了多种恶唑啉，包括五元和六元杂环以及碘、溴和氯甲基恶唑啉。值得注意的是，这种电化学氧化环化避免了使用外部氧化剂。

  DOI：

  10.1039/d1nj04819h

文献信息

• Electrochemical Chalcogenation of <i>β,γ</i> ‐Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines
  作者：Samrat Mallick、Mrinmay Baidya、Kingshuk Mahanty、Debabrata Maiti、Suman De Sarkar

  DOI：10.1002/adsc.201901262

  日期：2020.3.4

  The current report represents a transition‐metal‐free synthesis of oxazoline and isoxazoline derivatives by a tandem electro‐oxidative chalcogenation‐cyclization process. Both C−Se and C−S bond‐forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline

  本报告显示了通过串联电氧化硫属元素化-环化过程的无过渡金属合成恶唑啉和异恶唑啉衍生物。C-Se和C-S键形成方案均不使用任何外部氧化剂而开发，并且反应在室温下进行，并且对空气开放。使用这种方法，合成了29个取代的恶唑啉和16个取代的异恶唑啉衍生物，分离产率高达91％。
• Metal-Free Oxidative Functionalization of C(sp³)–H Bond Adjacent to Oxygen and Radical Addition to Olefins
  作者：Wei Zhou、Ping Qian、Jincan Zhao、Hong Fang、Jianlin Han、Yi Pan

  DOI：10.1021/acs.orglett.5b00088

  日期：2015.3.6

  A DTBP-promoted oxidative functionalization of a C(sp3)–H bond adjacent to oxygen and intermolecular radical addition to olefins without use of any metal catalyst or photoredox catalysis is reported. The reaction has a wide scope of olefin, alcohol, and cycloether substrates, which provides an easy way for direct preparation of α,ω-amino alcohols.

  据报道，在不使用任何金属催化剂或光氧化还原催化的情况下，DTBP促进了与氧相邻的C（sp 3）-H键的氧化功能化以及将分子间自由基加成至烯烃。该反应具有广泛的烯烃，醇和环醚底物范围，这为直接制备α，ω-氨基醇提供了简便的方法。
• Benzenesulfonamide derivatives
  申请人：Utsunomiya University

  公开号：US04157257A1

  公开（公告）日：1979-06-05

  A compound of the general formula ##STR1## wherein R.sub.0 represents an alkyl group optionally having a substituent selected from the class consisting of a cyano group, lower alkoxy groups and di-(lower alkyl)amino groups, a lower alkenyl group, or a lower alkynyl group; R.sub.1, R.sub.2 and R.sub.3, independently from each other, represent a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group; R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8, independently from each other, represent a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group; Y represents a group of the formula ##STR2## or a group of the formula ##STR3## in which one of R.sub.9 and R.sub.10 is a lower alkyl group and the other is a hydrogen atom or a lower alkyl group; with the proviso that when Y is the group ##STR4## and R.sub.0 represents an unsubstituted alkyl group, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 do not represent hydrogen atoms at the same time. The compounds of formula (I) are produced by the reaction of the corresponding benzenesulfonamide derivatives with the corresponding benzyl or benzoyl halides; the reaction of the corresponding benzenesulfonyl halides with the corresponding benzylamines or benzoyl amides; or by the alkylation, alkenylation or alkynylation of the corresponding compounds of formula (I) in which R.sub.0 is hydrogen. The compounds of formula (I) have superior selective herbicidal effects, and are useful as active ingredients of herbicides, especially those for application to aquatic rice paddies.

  一般式为##STR1##的化合物，其中R.sub.0代表一种烷基，可选地具有从类别中选择的取代基，该类别包括氰基，较低的烷氧基和二（较低的烷基）氨基基团，较低的烯基或较低的炔基；R.sub.1，R.sub.2和R.sub.3独立地表示氢原子，卤素原子，较低的烷基或较低的烷氧基；R.sub.4，R.sub.5，R.sub.6，R.sub.7和R.sub.8独立地表示氢原子，卤素原子，较低的烷基或较低的烷氧基；Y表示公式##STR2##的基团或公式##STR3##的基团，在其中R.sub.9和R.sub.10中的一个是较低的烷基，另一个是氢原子或较低的烷基；但是当Y是##STR4##基团且R.sub.0表示未取代的烷基时，R.sub.4，R.sub.5，R.sub.6，R.sub.7和R.sub.8不同时表示氢原子。公式（I）的化合物通过将相应的苯磺酰胺衍生物与相应的苯甲基或苯甲酰卤化物反应产生；将相应的苯磺酰卤与相应的苯甲胺或苯甲酰酰胺反应产生；或通过烷基化，烯基化或炔基化相应的公式（I）化合物，其中R.sub.0为氢。公式（I）的化合物具有优异的选择性除草效果，并且可用作除草剂的活性成分，特别是用于水田的除草剂。
• Novel benzenesulfonamide derivatives
  申请人：Utsunomiya University

  公开号：US04233061A1

  公开（公告）日：1980-11-11

  A compound of the general formula ##STR1## wherein R.sub.0 represents an alkyl group optionally having a substituent selected from the class consisting of a cyano group, lower alkoxy groups and di-(lower alkyl)amino groups, a lower alkenyl group, or a lower alkynyl group; R.sub.1, R.sub.2 and R.sub.3, independently from each other, represent a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group; R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8, independently from each other, represent a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group; Y represents a group of the formula ##STR2## or a group of the formula ##STR3## in which one of R.sub.9 and R.sub.10 is a lower alkyl group and the other is a hydrogen atom or a lower alkyl group; with the proviso that when Y is the group ##STR4## and R.sub.0 represents an unsubstituted alkyl group, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 do not represent hydrogen atoms at the same time. The compounds of formula (I) are produced by the reaction of the corresponding benzenesulfonamide derivatives with the corresponding benzyl or benzoyl halides; the reaction of the corresponding benzenesulfonyl halides with the corresponding benzylamines or benzoyl amides; or by the alkylation, alkenylation or alkynylation of the corresponding compounds of formula (I) in which R.sub.0 is hydrogen. The compounds of formula (I) have superior selective herbicidal effects, and are useful as active ingredients of herbicides, especially those for application to aquatic rice paddies.

  化合物的一般式为##STR1## 其中R0代表一个烷基，可以选择从以下类别中选取一个取代基：氰基、低级烷氧基和二-(低级烷基)氨基基团、低级烯基或低级炔基；R1、R2和R3独立地表示氢原子、卤素原子、低级烷基或低级烷氧基；R4、R5、R6、R7和R8独立地表示氢原子、卤素原子、低级烷基或低级烷氧基；Y表示以下式子的一种团：##STR2## 或以下式子的一种团：##STR3## 其中R9和R10中的一个是低级烷基，另一个是氢原子或低级烷基；但是当Y是##STR4## 团时，且R0表示未取代的烷基，R4、R5、R6、R7和R8不能同时表示氢原子。式(I)化合物是通过相应的苯磺酰胺衍生物与相应的苯甲基或苯甲酰卤化物反应而制得的；相应的苯磺酰卤化物与相应的苯甲胺或苯甲酰酰胺反应而制得；或通过烷基化、烯基化或炔基化相应的式(I)化合物，其中R0为氢。式(I)化合物具有卓越的选择性除草效果，并可用作除草剂的活性成分，特别是用于水稻田的除草剂。
• DE2744137
  申请人：——

  公开号：——

  公开（公告）日：——