N-(1-(naphthalen-2-yl)vinyl)acetamide | 177750-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1-(naphthalen-2-yl)vinyl)acetamide
• 英文别名: N-(1-(naphthalene-2-yl)vinyl)acetamide；N-(1-(2-naphthyl)vinyl)acetamide；N-(1-naphthalen-2-ylethenyl)acetamide
• CAS: 177750-24-2
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: WQZHIQOMXNMWGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1-(naphthalen-2-yl)vinyl)acetamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以55 mg的产率得到2-萘乙酮
  参考文献：
  名称：

  Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

  摘要：

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

  DOI：

  10.1021/jo050669u
• 作为产物：
  描述：

  2-萘乙酮 在 copper(l) iodide 、 盐酸羟胺 、 sodium acetate 、 sodium hydrogensulfite 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 N-(1-(naphthalen-2-yl)vinyl)acetamide
  参考文献：
  名称：

  将烯基CH活化与1，2-氧氮杂环丁烷的开环合并：钌催化的酰胺的氨基甲基化。

  摘要：

  1,2-氧氮杂环丁烷已被用作福尔马明的前体，用于Ru（II）物种下酰胺的直接氨甲基化。通过将烯基CH活化与1，2-氧杂环丁烷的开环合并，这种有效的方法为合成Z-选择性氨基甲基取代的酰胺提供了一种简便而新颖的方法。此外，两个示例性的合成细节突出了这种转化的潜力。

  DOI：

  10.1039/d0cc03081c

文献信息

• Modular Monodentate Phosphoramidite Ligands for Rhodium-Catalyzed Enantioselective Hydrogenation
  作者：Yan Liu、Kuiling Ding

  DOI：10.1021/ja052749l

  日期：2005.8.1

  A new class of monodentate phosphoramidite ligands (DpenPhos) has been developed on the basis of the modular concept for Rh(I)-catalyzed asymmetric hydrogenations of a variety of olefin derivatives, affording the corresponding optically active compounds in excellent yields and enantioselectivities. The ligands have the advantages of facile preparation, tunable structure, and broad scope of substrates

  基于 Rh(I) 催化的各种烯烃衍生物的不对称氢化的模块化概念，开发了一类新的单齿亚磷酰胺配体 (DpenPhos)，以优异的产率和对映选择性提供相应的光学活性化合物。这些配体在其 Rh(I) 络合物催化的不对称氢化中具有制备容易、结构可调和底物范围广等优点。
• Synthesis of Chiral Hydroxyl Phospholanes from <scp>d</scp>-mannitol and Their Use in Asymmetric Catalytic Reactions
  作者：Wenge Li、Zhaoguo Zhang、Dengming Xiao、Xumu Zhang

  DOI：10.1021/jo000066c

  日期：2000.6.1

  Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis-Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino

  手性羟基一膦3 [（2S，3S，4S，5S）-3,4-二羟基-2，5-二甲基-1-苯基膦烷]和双膦酸酯5a [1,2-双[（2S，3S，4S，5S） -3,4-二羟基-2,5-二甲基磷杂环戊烷基]苯]和5b [1,2-双[（2S，3S，4S，5S）-2,5-二乙基-3,4-二羟基磷杂环戊基]苯]从现成的D-甘露醇中以高收率获得。已经研究了在膦存在下保护和脱保护OH-基团的策略。当使用羟基膦作为催化剂时，在Baylis-Hillman反应中观察到速率加速。铑与手性双膦酸酯的络合物是高度对映选择性的催化剂，用于各种官能化烯烃（如脱氢氨基酸衍生物，衣康酸衍生物和烯酰胺）的不对称氢化。
• Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides
  作者：Xi-Hao Chang、Zi-Lu Wang、Meng Zhao、Chao Yang、Jie-Jun Li、Wei-Wei Ma、Yun-He Xu

  DOI：10.1021/acs.orglett.9b04645

  日期：2020.2.21

  A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C-C moieties to the products

  已开发出一种新型的酰胺类无金属脱氢甲硅烷基化方法。以中等至良好的产率和高的立体选择性获得了所需的官能化乙烯基硅烷产物。该协议显示出对各种功能的良好耐受性。此外，该反应的高化学选择性使我们能够向产物中引入不同的不饱和CC部分。产品进一步衍生为其他有用化合物的难易程度也证明了当前方法的高度合成效用。
• Direct Enamido C(sp²)−H Diphosphorylation Enabled by a PCET‐Triggered Double Radical Relay: Access to<i>gem</i>‐Bisphosphonates
  作者：Hao‐Qiang Cao、Hao‐Nan Liu、Zhe‐Yuan Liu、Bao‐Kun Qiao、Fa‐Guang Zhang、Jun‐An Ma

  DOI：10.1002/chem.202000517

  日期：2020.4.24

  electron-transfer (PCET)-triggered enamido C(sp2 )-H diphosphorylation. This reaction represents a rare example of realizing the challenging double C-P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves

  在这里，我们报告通过质子耦合电子转移（PCET）触发的烯键式C（sp2）-H双磷酸化来构造有价值的gem-BP的新颖而直接的协议。该反应代表了一个难得的例子，该例子实现了在单个碳原子上形成具有挑战性的双CP键，从而在银介导的条件下轻松地从简单的酰胺中获得了多种结构多样的双膦酸酯。初步的机理研究表明，二磷酸化涉及两轮PCET引发的自由基中继过程。
• BABIPhos Family of Biaryl Dihydrobenzooxaphosphole Ligands for Asymmetric Hydrogenation
  作者：Guisheng Li、Olga V. Zatolochnaya、Xiao-Jun Wang、Sonia Rodríguez、Bo Qu、Jean-Nicolas Desrosiers、Hari P. R. Mangunuru、Soumik Biswas、Daniel Rivalti、Shuklendu D. Karyakarte、Joshua D. Sieber、Nelu Grinberg、Ling Wu、Heewon Lee、Nizar Haddad、Daniel R. Fandrick、Nathan K. Yee、Jinhua J. Song、Chris H. Senanayake

  DOI：10.1021/acs.orglett.8b00139

  日期：2018.4.6

  Novel bidentate phosphine ligands BABIPhos featuring a biaryl bis-dihydrobenzooxaphosphole core are presented. Their synthesis was achieved via Pd-catalyzed reductive homocoupling of dihydrobenzooxaphosphole aryl triflates. An efficient route toward various analogues was also established, giving access to phosphines with different electronic and steric properties. The newly obtained ligands demonstrated

  提出了具有联芳基双-二氢苯并恶唑膦核的新型双齿膦配体BABIPhos。它们的合成是通过Pd催化的二氢苯并氧杂磷酰基芳基三氟甲磺酸酯的还原均偶联来实现的。还建立了通往各种类似物的有效途径，从而获得了具有不同电子和空间特性的膦。新获得的配体在Rh催化的二取代和三取代的酰胺的不对称加氢中显示出高效率和选择性。这类新的配体是对先前描述的双齿苯并恶唑磷配体BIBOP的补充。