N-buta-2,3-dienyl-toluene-4-sulfonanilide

• 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-buta-2,3-dienyl-toluene-4-sulfonanilide
• 英文别名: N-Buta-2,3-dienyl-toluol-4-sulfonanilid
• 化学式: C₁₇H₁₇NO₂S
• 分子量: 299.393
• InChiKey: XLEYBABPUODPJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-buta-2,3-dienyl-toluene-4-sulfonanilide 在 lithium aluminium tetrahydride 、 四(亚磷酸三苯酯)镍 、 抗氧剂168 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  镍催化下三组分交叉偶联反应催化碳-碳三键的氰化反应

  摘要：

  AbstractA nickel‐catalyzed three‐component coupling reaction through cyanation of a carbon‐carbon triple bond is described. A nickel(0) complex effectively catalyzes a sequential coupling reaction between allenes, alkynes and hydrogen cyanide from acetone cyanohydrin in a highly regio‐ and stereoselective fashion. The trigger for this reaction is hydronickelation to allenes. The initial hydride attack predominantly occurs at the central carbon of the allene to give a π‐allylnickel(II) species. Subsequent syn‐carbometalation connects a β‐carbon of alkynoates and a less‐hindered carbon of the allylnickel(II) species, and the corresponding cyanoalkenes are obtained as a single stereoisomer without any another organometallic reagents as a coupling partner.magnified image

  DOI：

  10.1002/adsc.201300553
• 作为产物：
  描述：

  4-methyl-N-phenyl-N-(prop-2-yn-1-yl)benzenesulfonamide 在 叠氮基三甲基硅烷 、 三氟化硼乙醚 、 silver carbonate 作用下， 以 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 1.5h， 生成 N-buta-2,3-dienyl-toluene-4-sulfonanilide
  参考文献：
  名称：

  乙烯基叠氮化物与烯丙基/炔丙基硅烷的形式施密特重排/ Hosomi-Sakurai反应中断

  摘要：

  据报道，N-甲苯磺酰基和S-取代的乙烯基叠氮化物的施密特重排/ Hosomi-Sakurai反应中断。以BF 3 ·Et 2 O作为路易斯酸助催化剂，乙烯基叠氮化物的脱氮片段化促进了N / S稳定的碳阳离子的生成，该碳阳离子进一步被烯丙基/炔丙基硅烷进行亲核加成以形成C-C键。结果，可以在温和的反应条件下以良好的收率和良好的官能团耐受性提供各种均烯丙基/烯丙基胺。

  DOI：

  10.1021/acs.orglett.8b03062

文献信息

• Hydrocyanative Cyclization and Three-Component Cross-Coupling Reaction between Allenes and Alkynes under Nickel Catalysis
  作者：Shigeru Arai、Yuka Amako、Xiaofei Yang、Atsushi Nishida

  DOI：10.1002/anie.201303883

  日期：2013.7.29

  Packed with functionality: The key step in the title reactions with acetone cyanohydrin is a regioselective hydronickelation of allenes. Subsequent carbometalation of the alkyne followed by reductive elimination gave cyano‐functionalized tetrasubstituted alkenes in a regio‐ and stereoselective manner (see scheme; EWG=electron‐withdrawing group, Ts=p‐toluenesulfonyl).

  功能丰富：与丙酮氰醇反应的标题中的关键步骤是烯丙基的区域选择性加氢镍化反应。随后炔烃的碳金属化，然后进行还原消除，以区域和立体选择性的方式生成了氰基官能化的四取代烯烃（参见方案； EWG =吸电子基团，Ts =对甲苯磺酰基）。
• Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant
  作者：Gullapalli Kumaraswamy、Swargam Vijaykumar、Kukkadapu Ankamma、Vykunthapu Narayanarao

  DOI：10.1039/c6ob02033j

  日期：——

  The synthesis of regio- and stereoselective aryl substituted α,β-unsaturated aldehydes and ketones from activated allenes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air and triggered by visible light. The same starting materials under ideal anaerobic conditions led to the 2,3-diphenylselenation adduct with no trace of oxygenated products, demonstrating

  从活化的烯上合成了区域和立体选择性的芳基取代的α，β-不饱和醛和酮。这种温和的非金属氧化仅由良性环境空气驱动，并由可见光触发。在理想的厌氧条件下，相同的原料导致形成2,3-二苯硒化加合物，而没有痕量的氧化产物，这表明溶解氧是两个不同反应路径的化学开关。该协议的显着特征是通过辐照两个有机分子之一实现的单电子转移（SET），从而避免了敏化剂形成自由基离子对。
• US2136177
  申请人：——

  公开号：——

  公开（公告）日：——
• Interruption of Formal Schmidt Rearrangement/Hosomi–Sakurai Reaction of Vinyl Azides with Allyl/Propargylsilanes
  作者：Guichun Fang、Zhenhua Liu、Shanshan Cao、Haiyan Yuan、Jingping Zhang、Ling Pan

  DOI：10.1021/acs.orglett.8b03062

  日期：2018.11.16

  An interrupted Schmidt rearrangement/Hosomi–Sakurai reaction of N-tosyl and S-substituted vinyl azides is reported. With BF3·Et2O as a Lewis acid promoter, the denitrogenative fragmentation of vinyl azides facilitates the generation of the N/S-stabilized carbocations, which further undergo nucleophilic addition by allyl/propargylsilanes for C–C bond formation. As a result, a variety of homoallylic/allenylic

  据报道，N-甲苯磺酰基和S-取代的乙烯基叠氮化物的施密特重排/ Hosomi-Sakurai反应中断。以BF 3 ·Et 2 O作为路易斯酸助催化剂，乙烯基叠氮化物的脱氮片段化促进了N / S稳定的碳阳离子的生成，该碳阳离子进一步被烯丙基/炔丙基硅烷进行亲核加成以形成C-C键。结果，可以在温和的反应条件下以良好的收率和良好的官能团耐受性提供各种均烯丙基/烯丙基胺。
• Catalytic Cyanation of Carbon-Carbon Triple Bonds Through a Three-Component Cross-Coupling Reaction under Nickel Catalysis
  作者：Xiaofei Yang、Shigeru Arai、Atsushi Nishida

  DOI：10.1002/adsc.201300553

  日期：2013.10.11

  AbstractA nickel‐catalyzed three‐component coupling reaction through cyanation of a carbon‐carbon triple bond is described. A nickel(0) complex effectively catalyzes a sequential coupling reaction between allenes, alkynes and hydrogen cyanide from acetone cyanohydrin in a highly regio‐ and stereoselective fashion. The trigger for this reaction is hydronickelation to allenes. The initial hydride attack predominantly occurs at the central carbon of the allene to give a π‐allylnickel(II) species. Subsequent syn‐carbometalation connects a β‐carbon of alkynoates and a less‐hindered carbon of the allylnickel(II) species, and the corresponding cyanoalkenes are obtained as a single stereoisomer without any another organometallic reagents as a coupling partner.magnified image