(E)-4-methyl-N-(2-vinylbenzylidene)benzenesulfonamide | 1123755-02-1

• 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: (E)-4-methyl-N-(2-vinylbenzylidene)benzenesulfonamide
• 英文别名: (NE)-N-[(2-ethenylphenyl)methylidene]-4-methylbenzenesulfonamide
• CAS: 1123755-02-1
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: FMAOVTJZBNJFRD-SFQUDFHCSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  453.4±48.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-methyl-N-(2-vinylbenzylidene)benzenesulfonamide 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以74%的产率得到N-(1H-inden-1-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Cu（OTf）2催化简单烯烃与α，β-不饱和羰基分子内直接共轭加成

  摘要：

  已经开发出前所未有的简单烯烃向α，β-不饱和羰基化合物的分子内共轭加成。发现一种简单的路易斯酸（例如Cu（OTf）2）可以有效地催化该反应，并以中等至高收率获得了六元和五元环状产物。

  DOI：

  10.1021/ol502373u
• 作为产物：
  描述：

  邻溴苯甲醛 在 palladium diacetate 、 四氯化钛 、 caesium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (E)-4-methyl-N-(2-vinylbenzylidene)benzenesulfonamide
  参考文献：
  名称：

  光氧化还原催化的三组分串联过程：复杂的三氟甲基化邻苯二酚和异吲哚啉的组装。

  摘要：

  一种新颖的光氧化还原介导的串联三组分工艺以可观的收率和中等至极好的非对映选择性提供了多种含CF3的邻苯二甲酸和异吲哚啉。

  DOI：

  10.1021/acs.orglett.6b01257

文献信息

• Photoredox-Catalyzed Three-Component Tandem Process: An Assembly of Complex Trifluoromethylated Phthalans and Isoindolines
  作者：Lucie Jarrige、Aude Carboni、Guillaume Dagousset、Guillaume Levitre、Emmanuel Magnier、Géraldine Masson

  DOI：10.1021/acs.orglett.6b01257

  日期：2016.6.17

  A novel photoredox-mediated tandem three-component process afforded a wide variety of CF3-containing phthalans and isoindolines in respectable yields and with moderate to excellent diastereoselectivity.

  一种新颖的光氧化还原介导的串联三组分工艺以可观的收率和中等至极好的非对映选择性提供了多种含CF3的邻苯二甲酸和异吲哚啉。
• Stereoselective Synthesis of Chiral IBR2 Analogues
  作者：Xiao-Long Qiu、Jiewen Zhu、Guikai Wu、Wen-Hwa Lee、A. Richard Chamberlin

  DOI：10.1021/jo802607f

  日期：2009.3.6

  Two stereoselective routes were developed to synthesize optically pure IBR2 analogues 1-16. The first features addition of N-Boc-3-bromoindole 26 to the sulfinamide 25, providing a 1: 1 ratio of the separable diasteroisomers 27 and 28 in good yield. In a straightforward fashion, the sulfinamides 27 and 28 were conveniently converted into the key amines 39 and 47 over 8 steps, respectively, from which a series of 3,4-dihydroisoquinolinyl IBR2 analogues 1-14 containing fluorinated and trifluoromethylated benzyl groups were prepared. Another route highlights the highly enantioselective addition of indole to the sulfonyl amide 50 with bifunctional aminothioureas 57 and 58 as catalysts. After the reaction conditions were optimized, the desired sulfonyl amides (R)-55 and (S)-55 were obtained in 99% ee and 98% ee, respectively. Acylation of (R)-55 and (S)-55 separately and subsequent allylation gave compounds 60 and 63, respectively, which were further subjected to RCM to furnish compounds 61 and 64 and, after removal of the Boc groups, the desired IBR2 analogues 15 and 16.
• Direct Intramolecular Conjugate Addition of Simple Alkenes to α,β-Unsaturated Carbonyls Catalyzed by Cu(OTf)₂
  作者：Yan Qin、Jian Lv、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1021/ol502373u

  日期：2014.10.3

  An unprecedented intramolecular conjugate addition of simple alkenes to α,β-unsaturated carbonyl compounds has been developed. A simple Lewis acid such as Cu(OTf)2 was found to effectively catalyze the reaction, and six- and five-membered cyclic products were obtained in moderate to high yields.

  已经开发出前所未有的简单烯烃向α，β-不饱和羰基化合物的分子内共轭加成。发现一种简单的路易斯酸（例如Cu（OTf）2）可以有效地催化该反应，并以中等至高收率获得了六元和五元环状产物。
• Enantioselective synthesis of 1-aminoindene derivatives <i>via</i> asymmetric Brønsted acid catalysis
  作者：Xiang Wu、Du Ding、Ying Zhang、Hua-Jie Jiang、Tao Wang、Li-Ping Zhao

  DOI：10.1039/d1cc03568a

  日期：——

  describe a catalytic asymmetric iminium ion cyclization reaction of simple 2-alkenylbenzaldimines using a BINOL-derived chiral N-triflyl phosphoramide. The corresponding 1-aminoindenes and tetracyclic 1-aminoindanes are formed in good yields and high enantioselectivities. Further, the chemical utility of the obtained enantiopure 1-aminoindene is demonstrated for the asymmetric synthesis of (S)-rasagiline

  我们描述了使用 BINOL 衍生的手性N-三氟甲基磷酰胺的简单 2-烯基苯甲醛二亚胺的催化不对称亚胺离子环化反应。相应的 1-氨基茚和四环 1-氨基茚以良好的产率和高对映选择性形成。此外，所获得的对映体纯 1-氨基茚的化学效用被证明用于 ( S )-雷沙吉兰的不对称合成。