2-hexyl-acryloyl chloride | 99061-95-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2-hexyl-acryloyl chloride
• 英文别名: 2-Methyleneoctanoyl chloride；2-methylideneoctanoyl chloride
• CAS: 99061-95-7
• 化学式: C₉H₁₅ClO
• 分子量: 174.671
• InChiKey: FWJZUCSNBXHQDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-hexyl-acryloyl chloride 在 sodium azide 作用下， 生成 1-hexyl-vinyl isocyanate
  参考文献：
  名称：

  Studies on l-Alkenyl Isocyanates and Their Derivatives¹

  摘要：

  DOI：

  10.1021/jo01062a031
• 作为产物：
  描述：

  alpha-羧基异辛酸 在 草酰氯 、 二乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 2-hexyl-acryloyl chloride
  参考文献：
  名称：

  Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling

  摘要：

  A Ni-catalyzed enantioselective reductive diarylation of activated alkenes by domino cyclizative/ cross-coupling of two aryl bromides is developed. This reaction proceeds under very mild conditions and shows broad substrate scope, without requiring the use of preformed organometallic reagents. Moreover, this approach provides direct access to various bis-heterocycles bearing all-carbon quaternary centers in synthetically useful yields (up to 81%) with excellent enantioselectivity (>30 examples, 90-99% ee).

  DOI：

  10.1021/jacs.8b08190

文献信息

• Arylphosphonylation and Arylazidation of Activated Alkenes
  作者：Wangqing Kong、Estíbaliz Merino、Cristina Nevado

  DOI：10.1002/anie.201311241

  日期：2014.5.12

  Two radical‐mediated processes of activated alkenes, namely arylphosphonylation and arylazidation, are described. The difunctionalization of alkenes by a tandem process that involves radical addition, 1,4‐aryl migration, and desulfonylation generates α‐aryl‐β‐heterofunctionalized amides bearing a quaternary stereocenter when the substituent on the nitrogen atom is an aryl group. Alternatively, heterooxindoles

  描述了活化烯烃的两个自由基介导的过程，即芳基膦酰化和芳基叠氮化。当氮原子上的取代基为芳基时，通过自由基加成，1,4-芳基迁移和脱磺酰作用的串联双烯烃双官能化反应会生成带有季立体中心的α-芳基-β-杂官能化酰胺。或者，可以在氮原子上存在烷基取代基的情况下，以优异的区域选择性获得杂吲哚或螺二环。
• Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C–H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole
  作者：Wangqing Kong、Qian Wang、Jieping Zhu

  DOI：10.1021/jacs.5b11625

  日期：2015.12.30

  Intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by intermolecular trapping of the resulting σ-C(sp(3))-Pd complex by azoles afforded 3,3-disubstituted oxindoles in good yields with excellent enantioselectivities. Two C-C bonds were created with concurrent formation of an all-carbon quaternary stereocenter. Oxadiazole substituted oxindoles were subsequently converted to pyrroloindolines

  N-芳基丙烯酰胺的分子内不对称碳钯化，然后用唑类分子间捕获所得的 σ-C(sp(3))-Pd 复合物，以良好的收率和出色的对映选择性提供了 3,3-二取代的羟吲哚。创建了两个 CC 键，同时形成了一个全碳四元立体中心。恶二唑取代的羟吲哚随后通过前所未有的还原环化方案转化为吡咯并二氢吲哚。(+)-esermethole 的对映选择性合成说明了这种化学的效用。
• Rh^III-Catalyzed C–H (Het)arylation/Vinylation of <i>N</i>-2,6-Difluoroaryl Acrylamides
  作者：Huai-Wei Wang、Yu-Han Qiao、Jia-Xue Wu、Qiu-Ping Wang、Meng-Xin Tian、Yong-Fei Li、Qing-Xia Yao、Da-Cheng Li、Jian-Min Dou、Yi Lu

  DOI：10.1021/acs.orglett.0c03688

  日期：2021.2.5

  RhIII-catalyzed sp2 C–H cross-coupling of acrylamides with organoboron reactants has been accomplished using a commercially available N-2,6-difluoroaryl acrylamide auxiliary. A broad range of aryl and vinyl boronates as well as a variety of heterocyclic boronates with strong coordinating ability can serve as the coupling partners. This transformation proceeds under moderate reaction conditions with excellent

  丙烯酰胺与有机硼反应物的Rh III催化的sp 2 C–H交叉偶联已使用市售的N -2,6-二氟芳基丙烯酰胺助剂完成。广泛的芳基和乙烯基硼酸酯以及各种具有强配位能力的杂环硼酸酯都可以用作偶联伙伴。该转化在中等反应条件下进行，具有优异的官能团耐受性和高区域选择性。
• Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles
  作者：Yuxiu Li、Kuai Wang、Yuanyuan Ping、Yifan Wang、Wangqing Kong

  DOI：10.1021/acs.orglett.7b03713

  日期：2018.2.16

  The first nickel-catalyzed domino Heck cyclization/Suzuki coupling reaction for the synthesis of 3,3-disubstituted oxindoles bearing quaternary all-carbon centers is reported. A wide range of electrophiles, such as aryl iodides, bromides, triflates, and chlorides, are all compatible with the reaction conditions. Moreover, cheap aryl esters, which undergo catalytic C–O bond cleavage, could also be employed

  报道了第一个镍催化的多米诺Heck环化/ Suzuki偶联反应，用于合成带有季全碳中心的3,3-二取代的羟吲哚。各种各样的亲电试剂，例如芳基碘化物，溴化物，三氟甲磺酸盐和氯化物，都与反应条件兼容。此外，廉价的芳基酯经过催化的C-O键裂解，也可以用作亲电子试剂。该方法显示出良好的产率和广泛的范围，补充了常规钯基类似物的更实用和可持续的替代方法。
• Ni‐Catalyzed Divergent Synthesis of 2‐Benzazepine Derivatives via Tunable Cyclization and 1,4‐Acyl Transfer Triggered by Amide N‐C Bond Cleavage
  作者：Yuanyuan Ping、Xiao Li、Qi Pan、Wangqing Kong

  DOI：10.1002/anie.202201574

  日期：2022.6.20

  Ni-catalyzed ligand-controlled tunable cyclization/cross-couplings was developed for the divergent synthesis of pharmacologically important 2-benzazepine frameworks. The bidentate ligand facilitates the formation of 2-benzazepin-5-ones and benzo[c]pyrano[2,3-e]azepines. The tridentate ligand promotes the formation of 2-benzazepin-3-ones.

  镍催化配体控制的可调环化/交叉偶联被开发用于药理学上重要的 2-苯并氮杂框架的不同合成。双齿配体促进 2-benzazepin-5-ones 和苯并[c]pyrano[2,3-e]azepines 的形成。三齿配体促进 2-苯并氮杂 3-ones 的形成。