2-(2,2-dichloroethenyl)benzenamine | 54143-01-0

• 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: 2-(2,2-dichloroethenyl)benzenamine
• 英文别名: 2-(2,2-dichlorovinyl)-phenylamine；2-(2,2-dichloro-vinyl)-phenylamine；2-(2,2-Dichlorethinyl)anilin；2-(2,2-Dichloroethenyl)aniline
• CAS: 54143-01-0
• 化学式: C₈H₇Cl₂N
• 分子量: 188.056
• InChiKey: KOBKKRQJMJGILK-UHFFFAOYSA-N

物化性质

• 沸点：
  289.5±30.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,2-dichloroethenyl)benzenamine 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1-(2,2-dichloroethenyl)-2-isocyanobenzene
  参考文献：
  名称：

  One-Pot Synthesis ofN,N-Disubstituted (Z)-4-(Halomethylidene)-4H-3,1-benzothiazin-2-amines from 2-(2,2-Dihaloethenyl)phenyl Isothiocyanates and Secondary Amines

  摘要：

  AbstractWe have developed a one‐pot procedure for the preparation of N,N‐disubstituted (Z)‐4‐(halomethylidene)‐4H‐3,1‐benzothiazin‐2‐amines 3 from 2‐(2,2‐dihaloethenyl)phenyl isothiocyanates 1, easily accessible from known 2‐(2,2‐dihaloethenyl)benzenamines by a three‐step sequence, and secondary amines. Thus, the isothiocyanates 1 react with secondary amines to afford the corresponding thiourea derivatives, of which the treatment with NaH provides the desired products.

  DOI：

  10.1002/hlca.201300357
• 作为产物：
  描述：

  邻硝基苯甲醛 在 氯化铵 、 锌 作用下， 生成 2-(2,2-dichloroethenyl)benzenamine
  参考文献：
  名称：

  Onium ions. XIV. Evidence for the formation of benzochlorophenium ions

  摘要：

  DOI：

  10.1021/jo00896a025

文献信息

• [EN] AGRICULTURAL CHEMICALS<br/>[FR] SUBSTANCES AGROCHIMIQUES
  申请人：REDAG CROP PROT LTD

  公开号：WO2017178819A1

  公开（公告）日：2017-10-19

  The present invention relates to compounds which are of use in the field of agriculture as fungicides.

  本发明涉及在农业领域作为杀菌剂使用的化合物。
• A Highly Selective Tandem Cross-Coupling of <i>gem</i>-Dihaloolefins for a Modular, Efficient Synthesis of Highly Functionalized Indoles
  作者：Yuan-Qing Fang、Mark Lautens

  DOI：10.1021/jo701987r

  日期：2008.1.1

  A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline

  使用吲哚合成法的高效率的方法偕- dihalovinylaniline底物和有机硼试剂经由Pd催化的分子内串联胺化和分子间Suzuki偶联显影。芳基，烯基和烷基硼试剂均已成功使用，从而形成了一种通用的模块化方法。该反应耐受苯胺上的多种取代方式，从而导致吲哚类化合物的基团在C 2 -C 7处。铜和钯介导的1,2-二芳基吲哚顺序合成的正交方法开发了多种有机硼试剂的广泛应用。
• Synthesis of 2-Aryl-(Z)-4-(halomethylidene)-4H-3,1-benzoxazines by Sodium Hydride Mediated Cyclization of N-[2-(2,2-Dihaloethenyl)phenyl]arenecarboxamides
  作者：Kazuhiro Kobayashi、Ippei Nozawa、Daiki Kado

  DOI：10.3987/com-14-13127

  日期：——

  study has shown that 2-(2,2-dihaloethenyl)phenyl isothiocyanates were easily prepared from the respective 2-(2,2-dihaloethenyl)benzenamines and that the corresponding thiourea derivatives, derived from these isothiocyanates and secondary amines, underwent ring closure on treatment with sodium hydride to result in the stereoselective formation of N,N-disubstituted (Z)-4-(halomethylidene)-4H-3,1benzothiazin-2-amines

  开发了一种简单的两步法，用于从容易获得的 2-(2,2dihaloethenyl)benzenamines 制备 2-aryl-(Z)-4(halomethylidene)-4H-3,1-benzoxazines。因此，这些胺用各自的芳酰氯进行N-芳酰化，得到N-[2-(2,2二卤代乙烯基)苯基]芳烃甲酰胺，再用氢化钠处理得到所需产物。引言 由于 4-亚烷基-4H-3,1-苯并恶嗪衍生物在合成上具有重要意义，因此最近报道了许多制备此类分子的方法。另一方面，我们之前的研究表明，2-(2,2-二卤代乙烯基)苯基异硫氰酸酯很容易从各自的 2-(2,2-二卤代乙烯基)苯胺和衍生自这些异硫氰酸酯的相应硫脲衍生物和仲胺，用氢化钠处理后进行闭环，导致立体选择性地形成 N,N-二取代 (Z)-4-(卤代亚甲基)-4H-3,1benzothiazin-2-amines。因此，我们对扩展这种类型的闭环以构建 (Z)-4-(卤代亚甲基)-4H-3
• Screening Methods
  申请人：Lautens Mark

  公开号：US20080039625A1

  公开（公告）日：2008-02-14

  Disclosed are processes for the preparation of 2-substituted indole compounds wherein the 2-substituent comprises an R 4 group, wherein R 4 is selected from the group consisting of monocyclic aromatic, polycyclic aromatic, monocyclic heteroaromatic, polycyclic heteroaromatic, 1° alkyl, and alkenyl, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents, and wherein R 4 is bonded to the 2-position of the indole ring via a C—C bond; the process comprising reacting an orthogem-dihalovinylaniline compound of the formula (I): wherein Halo comprises Br, Cl, or I; each of the one or more R 1 is independently selected from the group consisting of H, fluoro, lower alkyl, lower alkenyl, lower alkoxy, aryloxy, lower haloalkyl, lower alkenyl, —C(O)O-lower alkyl, monocyclic or polycyclic aryl or heteroaryl moiety, or R 1 is an alkenyl group bonded so to as to form a 4- to 20-membered fused monocycle or polycyclic ring with the indole ring; all of which are optionally substituted with one or more suitable substituents at one or more substitutable positions; R 2 comprises H, alkyl, cycloalkyl, aryl, heteroaryl, aryl-loweralkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; R 3 comprises H, alkyl, haloalkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aryl-(C 1-6 )alkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; with an organoboron reagent selected from the group consisting of a boronic ester of R 4 , a boronic acid of R 4 , a boronic acid anhydride of R 4 , a trialkylborane of R 4 and a 9-BBN derivative of R 4 ; in the presence of a base, a palladium metal pre-catalyst and a ligand under reaction conditions effective to form the 2-substituted indole compound. Also disclosed are processes for the preparation of ortho-gem-dihalovinylaniline compounds. Novel compounds prepared by the processes and novel uses of the compounds are likewise disclosed.

  本发明涉及制备2-取代吲哚化合物的方法，其中2-取代基包括R4基团，其中R4从单环芳香族、多环芳香族、单环杂芳族、多环杂芳族、1°烷基和烯基中选择，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换，并且其中R4通过C-C键与吲哚环的2-位置结合；该方法包括将式（I）的正交二卤代乙烯基苯胺化合物与来自以下组的有机硼试剂反应：其中Halo包括Br、Cl或I；其中一个或多个R1各自独立地选择自H、氟、低烷基、低烯基、低烷氧基、芳氧基、低卤代烷基、低烯基、-C（O）O-低烷基、单环或多环芳基或杂芳基基团，或者R1是一个烯基团，通过与吲哚环形成一个4到20个成员的融合的单环或多环环，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；R2包括H、烷基、环烷基、芳基、杂芳基、芳基-低烷基-或杂芳基-低烷基-，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；R3包括H、烷基、卤代烷基、烯基、炔基、芳基、杂芳基、环烷基、杂环、芳基-(C1-6)烷基-或杂芳基-低烷基-，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；在碱、钯金属预催化剂和配体存在下，以有效的反应条件形成2-取代吲哚化合物。本发明还涉及制备正交二卤代乙烯基苯胺化合物的方法。本发明还涉及通过上述方法制备的新化合物以及化合物的新用途。
• Rhodium‐Catalyzed Intramolecular Cyclization and Rearrangement of 1‐Azido‐2‐(2,2‐Dihalovinyl)arenes and 1‐Azido‐2‐[(2,2‐Dihalovinyl)(Boc)amino]arenes for the Preparation of 2,3‐Dihaloindoles and 2‐Haloquinoxalines
  作者：Teppei Abe、Kazuki Kobayashi、Seiya Kikukawa、Yuuki Kanai、Takeshi Hata

  DOI：10.1002/adsc.202300885

  日期：2023.12.19

  Treatment of 1-azido-2-(2,2-dihalovinyl)arenes with a catalytic amount of Rh2(esp)2 afforded various 2,3-dihaloindoles in 51–74% yields. This reaction progressed via the intramolecular cyclization of rhodium nitrene generated in situ and the rearrangement of one halogen group. For the 2-chloro-2-iodovinyl group, the iodo group selectively rearranged to yield 2-chloro-3-iodoindoles as single isomers

  用催化量的 Rh 2 (esp) 2处理 1-叠氮基-2-(2,2-二卤乙烯基)芳烃，得到各种 2,3-二卤吲哚，产率为 51-74%。该反应通过原位生成的铑氮宾的分子内环化和一个卤素基团的重排进行。对于2-氯-2-碘乙烯基，碘基选择性重排，产生单一异构体2-氯-3-碘吲哚。此外，1-叠氮基-2-[(2,2-二卤代乙烯基)(Boc)氨基]芳烃与催化量的Rh 2 (oct) 4反应，产生2-卤代喹喔啉，产率为55-92%。