(E)-N-benzyl-2-styrylaniline | 909297-33-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-N-benzyl-2-styrylaniline
• 英文别名: N-benzyl-2-[(E)-2-phenylethenyl]aniline
• CAS: 909297-33-2
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: PGFQOMLIYALVPJ-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-benzyl-2-styrylaniline 在 N-甲基哌啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 三乙胺 、 cobalt acetylacetonate 作用下， 以 癸烷 、 氯仿 为溶剂， 反应 24.0h， 生成 4-benzoyl-1-benzylquinolin-2(1H)-one
  参考文献：
  名称：

  钴盐催化的α-溴-N-苯基乙酰胺衍生物的碳环化反应†

  摘要：

  已经开发了一种高效且低成本的合成4-取代的喹啉-2-（1 H）-酮的方法。在TBHP的存在下，钴（II）催化芳基乙烯基取代的α-溴-N-苯基乙酰胺的碳环化反应，包括顺序的6 -exo-trig自由基环化，叔丁基过氧自由基交叉偶联反应和碱促进的离子Kornblum-DeLaMare反应生成4-苯甲酰基喹啉-2-（1 H）-一。各种有用的官能团例如甲氧基，氟，氯，溴，甲氧基羰基和氰基与反应条件相容。该策略进一步应用于芳基乙炔基取代的α-溴-N有效地形成了-苯基乙酰胺和4-苄基喹啉-2-（1 H）-一。

  DOI：

  10.1039/c7ob00009j
• 作为产物：
  描述：

  2-硝基苯乙酸 在 哌啶 、 sodium sulfide 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (E)-N-benzyl-2-styrylaniline
  参考文献：
  名称：

  纯空间位阻对分子内质子在激发态下的质子转移的影响以及在近红外激光辐照下共轭新染料的光物理性质

  摘要：

  这项研究提出了多种带有内部质子转移链段的新型扩展共轭染料，它们具有不同程度的空间位阻。此外，合成了缺乏质子转移部分的染料作为参考。1个1 H NMR谱和X射线单晶显示目标染料中存在内部氢键。研究表明，空间位阻较小或中等的目标染料在激发态下均表现出内部质子转移，因此在单光子和近红外双光子辐照下分别产生双发射带，而空间位阻较重的染料显示出在激发态下分子内质子转移发射相当弱，甚至没有。进一步进行了分子建模以了解空间位阻对目标染料在激发态下内部质子转移的抑制作用。

  DOI：

  10.1016/j.dyepig.2017.06.064

文献信息

• DMSO/SOCl₂-mediated C(sp²)–H amination: switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives
  作者：Jingran Zhang、Xiaoxian Li、Xuemin Li、Haofeng Shi、Fengxia Sun、Yunfei Du

  DOI：10.1039/d0cc07453e

  日期：——

  The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic

  发现2-烯基苯胺与SOCl 2在DMSO中的反应选择性地提供3-未取代的吲哚和3-甲基硫代吲哚。发现这种可转换的方法是温度依赖性的：在室温下，该反应通过分子内环化和消除得到3-未取代的吲哚；在较高温度下，反应通过进一步的亲电甲基硫醇化反应生成3-甲基硫吲哚。
• Room-Temperature Palladium-Catalyzed Intramolecular Oxidative Aminocarbonylation of Vinylic C(sp²)-H Bonds with Amines and CO
  作者：Xu-Heng Yang、Kai Li、Ren-Jie Song、Jin-Heng Li

  DOI：10.1002/ejoc.201301284

  日期：2014.1

  A new, mild route to access 3-methyleneindolin-2-ones is presented that proceeds through a room-temperature, palladium-catalyzed intramolecular oxidative aminocarbonylation of alkenes with amines and CO. This method represents a new aminocarbonylation strategy by employing an oxidative functionalization of a vinyl C(sp2)–H bond.

  提出了一种获得 3-亚甲基吲哚-2-酮的新的、温和的途径，该途径通过在室温下钯催化的烯烃与胺和 CO 的分子内氧化氨基羰基化进行。该方法代表了一种新的氨基羰基化策略，通过采用氧化功能化乙烯基 C(sp2)-H 键。
• Metal-Free C–H Amination for Indole Synthesis
  作者：Young Ho Jang、So Won Youn

  DOI：10.1021/ol5015398

  日期：2014.7.18

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.
• Carbolithiation of <i>o</i>-Amino-(<i>E</i>)-Stilbenes:  Diastereoselective Electrophile Substitution with Applications to Quinoline Synthesis
  作者：Anne-Marie L. Hogan、Donal F. O'Shea

  DOI：10.1021/jo7017679

  日期：2007.12.1

  [GRAPHICS]A regioselective carbolithiation of o-amino-(E)-stilbenes has been achieved with a series of alkyllithiums when THF is employed as the reaction solvent. The use of other solvents, such as diethyl ether or hydrocarbons, leads to a pronounced loss in regioselectivity. Moreover, high levels of diastereoselectivity have been obtained following reaction of the lithiated intermediate in THF with different electrophiles such as MeOD, CO2, and Bu3SnCl. It was shown that diastereoselectivity was influenced by the ortho-amino substituent and the alkyllithium utilized for carbolithiation with N-Boc substituent and t-BuLi proving optimal. In the case of carbolithiated intermediate 3a, obtained from the reaction of N-Boc substituted stilbene with t-BuLi, H-1 and C-13 NMR analysis revealed predominantly one diastereoisomer which was stable at room temperature. Application of the carbolithiation/electrophile reaction methodology to the synthesis of six-membered quinoline ring systems is demonstrated with substituted 3,4-dihydroquinolin-2-ones, 1,2,3,4-tetrahydroquinolines, 1,4-dihydroquinolines, and quinolines all prepared by a common cascade route.
• Regioselective Carbolithiation of <i>o</i>-Amino-(<i>E</i>)-Stilbenes:  Cascade Route to the Quinoline Scaffold
  作者：Anne-Marie L. Hogan、Donal F. O'Shea

  DOI：10.1021/ol061348n

  日期：2006.8.1

  The regioselective carbolithiation of substituted ortho-amino-(E)-stilbenes can be exploited to initiate cascade reaction sequences that can be utilized as new routes to substituted 3,4-dihydro-1H-quinolin-2-ones,1,2,3,4-tetrahydroquinolines, 1,4-dihydroquinolines, and quinolines.