N-cinnamyl-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide | 373640-90-5

• 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-cinnamyl-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
• 英文别名: 4-methyl-N-(3-phenylprop-2-enyl)-N-prop-2-ynylbenzenesulfonamide
• CAS: 373640-90-5
• 化学式: C₁₉H₁₉NO₂S
• 分子量: 325.431
• InChiKey: RPSOKXVCPNBLRU-UHFFFAOYSA-N

物化性质

• 沸点：
  488.3±55.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 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-cinnamyl-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 在 silver hexafluoroantimonate 、 [AuCl(C(NHTol-p)(NHMe))] 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以77%的产率得到3-benzylidene-1-tosyl-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Nitrogen Acyclic Gold(I) Carbenes: Excellent and Easily Accessible Catalysts in Reactions of 1,6-Enynes

  摘要：

  Complexes [AuCl{C(NHR)(NHR')}] and [AuCl{C(NHR)(NEt2)}] (R =Bu-t, p-Tol, Xylyl, p-C6H4-COOH, p-C6H4COOEt, R' = Me, Bu-n, Pr-i, (n)heptyl, p-Tol) have been prepared by reaction of the corresponding isocyanogold complexes [AuCl(CNR)] with either primary amines or diethylamine. All the prepared carbenes are reactive and highly selective catalysts for skeletal rearrangement, methoxycyclization of 1,6-enynes, and other mechanistically related gold-catalyzed transformations. Overall, these easily accessible nitrogen acyclic carbene (NAC) gold complexes were not second to NHC complexes and were advantageous to obtain different products.

  DOI：

  10.1021/om901026m
• 作为产物：
  描述：

  对甲苯磺酰氯 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 N-cinnamyl-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  烯类和烯类与分子氧的无金属多米诺寡环化反应

  摘要：

  已经描述了在3 O 2气氛下向C-C三键向苯环的氧桥联的七元环系统和aza [3.1.0]自行车骨架的无氧金属新的无金属直接加成。该反应至少通过三个分子内C–O和C–C键形成步骤，通过绿色，简单且前所未有的多米诺基自由基工艺进行，具有高选择性和高收率。

  DOI：

  10.1021/acs.orglett.0c04272

文献信息

• Radical Borylation/Cyclization Cascade of 1,6-Enynes for the Synthesis of Boron-Handled Hetero- and Carbocycles
  作者：Shi-Chao Ren、Feng-Lian Zhang、Jing Qi、Yun-Shuai Huang、Ai-Qing Xu、Hong-Yi Yan、Yi-Feng Wang

  DOI：10.1021/jacs.7b01889

  日期：2017.5.3

  construct boron-handled cyclic molecules was developed based on a radical borylation/cyclization cascade of 1,6-enynes. The process was initiated by the chemo- and regio-controlled addition of an N-heterocyclic carbene-boryl radical to an alkene or alkyne, followed by ring closure to afford boron-substituted cyclic skeletons. Further molecular transformations of the cyclic products to synthetically

  基于 1,6-烯炔的自由基硼化/环化级联，开发了一种构建硼处理环状分子的合成方法。该过程由化学和区域控制的 N-杂环卡宾硼基与烯烃或炔烃的加成开始，然后闭环以提供硼取代的环状骨架。还证明了环状产物向合成有用的结构单元的进一步分子转化。
• Visible‐Light‐Promoted Polycyclizations of Dienynes
  作者：Matteo Lanzi、Veronica Santacroce、Davide Balestri、Luciano Marchiò、Franca Bigi、Raimondo Maggi、Max Malacria、Giovanni Maestri

  DOI：10.1002/anie.201902837

  日期：2019.5.13

  A variety of linear dienynes can deliver complex tetracyclic frameworks in the presence of an IrIII complex and visible light. Product formation involves the generation of four new C−C bonds and six contiguous stereocenters, which decorate two [3.1.0] bicyclic units tethered through their bridging quaternary carbon atoms. The internal alkyne acts as a formal dicarbenoid for the generation of two cyclopropanes

  多种线性二烯可以在Ir III络合物和可见光存在下递送复杂的四环骨架。产物的形成涉及生成四个新的C-C键和六个连续的立体中心，它们装饰了两个[3.1.0]双环单元，这些单元通过它们的桥接季碳原子进行束缚。内部炔烃用作形式的二碳烯化合物，用于在这些自由基阳离子级联反应中生成两个环丙烷。对于有机反应性中间体，以前尚未观察到这种行为，并且可以扩展到分子间反应和二烯二炔。
• Rhodium(<scp>i</scp>)-catalyzed vinylation/[2 + 1] carbocyclization of 1,6-enynes with α-diazocarbonyl compounds
  作者：Junmin Huang、Xinwei Hu、Fengjuan Chen、Jiao Gui、Wei Zeng

  DOI：10.1039/c9ob01028a

  日期：——

  A sequential Rh(i)-catalyzed vinylation/[2 + 1]carbocyclization between enynes and diazo compounds has been developed. This transformation features a wide range of enynes and acceptor/acceptor diazo compounds, providing easy access to versatile vinyl-substituted azabicyclo[3.1.0]hexanes having a broad tolerance to functional groups.

  炔烃和重氮化合物之间的顺序Rh（i）催化的乙烯基化/ [2 +1]碳环化反应已经开发出来。该转化具有广泛的烯炔和受体/受体重氮化合物，可轻松获得对官能团具有宽容度的通用乙烯基取代的氮杂双环[3.1.0]己烷。
• Ambient Synthesis of Tricyclic Naphthalenes via Stepwise Styryl-yne Dearomative Diels–Alder Cyclization
  作者：Nicola Camedda、Matteo Lanzi、Franca Bigi、Raimondo Maggi、Giovanni Maestri

  DOI：10.1021/acs.orglett.1c02339

  日期：2021.8.20

  A cascade of styrylynols promoted by MnO2 allows the synthesis of fused tricycles with a naphthalene core. The reaction occurs under ambient conditions, offering a practical synthetic tool because of the inexpensive and abundant manganese species. The method affords products through the sequential oxidation of a propargyl alcohol, stepwise Diels–Alder cyclization, and finally rearomatization. According

  由 MnO 2促进的苯乙烯醇级联允许合成具有萘核的稠合三环。该反应在环境条件下发生，由于廉价且丰富的锰种类，提供了一种实用的合成工具。该方法通过炔丙醇的顺序氧化、逐步的 Diels-Alder 环化和最后的重构化得到产物。根据密度泛函理论，通常不利的逐步 Diels-Alder 机制反而是引发具有挑战性的脱芳香环化的通用工具。
• Visible-Light Mediated Hydrosilylative and Hydrophosphorylative Cyclizations of Enynes and Dienes
  作者：Hong Hou、Yue Xu、Haibo Yang、Xiaoyun Chen、Chaoguo Yan、Yaocheng Shi、Shaoqun Zhu

  DOI：10.1021/acs.orglett.0c00024

  日期：2020.3.6

  Described herein is a visible-light mediated intermolecular radical cyclization approach to access heterocycles. Heteroatom radicals, such as silicon and phosphorus atom radicals, were generated via direct hydrogen atom abstraction by the photoexcited catalyst species with hydro-silanes and phosphine oxides. The radical addition/cyclization/HAT (hydrogen atom transfer) reaction sequences of 1,6-enynes

  本文描述了可见光介导的分子间自由基环化方法，以接近杂环。杂原子基团，例如硅和磷原子基团，是由光激发的催化剂与氢硅烷和氧化膦通过直接氢原子的提取而产生的。1,6-烯炔和1,6-二烯的自由基加成/环化/ HAT（氢原子转移）反应顺序非常高效，可以高收率传递所需的杂环。