ethyl N-benzyl-N-(2-phenylethynyl)carbamate | 1422721-78-5

• 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: ethyl N-benzyl-N-(2-phenylethynyl)carbamate
• CAS: 1422721-78-5
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: ZJEFBFHXJLJQBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl N-benzyl-N-(2-phenylethynyl)carbamate 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以90%的产率得到(E)-ethyl benzyl(1-bromo-2-phenylvinyl)carbamate
  参考文献：
  名称：

  Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation

  摘要：

  A facile approach to (E)-alpha-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.101
• 作为产物：
  描述：

  苯乙炔 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 17.0h， 生成 ethyl N-benzyl-N-(2-phenylethynyl)carbamate
  参考文献：
  名称：

  Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation

  摘要：

  A facile approach to (E)-alpha-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.101

文献信息

• Stereoselective Synthesis of Pyrido- and Pyrrolo[1,2-<i>c</i>][1,3]oxazin-1-ones via a Nucleophilic Addition–Cyclization Process of <i>N</i>,<i>O</i>-Acetal with Ynamides
  作者：Pan Han、Zhuo-Ya Mao、Chang-Mei Si、Zhu Zhou、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1021/acs.joc.8b02795

  日期：2019.1.18

  An efficient asymmetric approach to access functionalized pyrido- and pyrrolo[1,2-c][1,3]oxazin-1-ones has been developed through a nucleophilic addition–cyclization process of N,O-acetal with ynamides. A number of substituted ynamides 8a–8o and 3-silyloxypyrrolidine or piperidine N,O-acetals 6a, 7 were amenable to this transformation, and the desired products 9a–9o, 10a–10m were obtained with excellent

  通过N，O-乙缩醛与ynamides的亲核加成环化过程，已经开发出一种有效的不对称途径来获得官能化的吡啶并吡咯并[1,2- c ] [1,3]恶嗪-1-酮。许多取代的酰胺8a - 8o和3-甲硅烷氧基吡咯烷或哌啶N，O-缩醛6a和7都适合这种转化，并获得了所需的产物9a - 9o，10a - 10m，具有优异的区域选择性和出色的非对映选择性。此外，手性乙酰胺14a– 14f也可能会经历这种加成环化过程，从而以极高的收率获得15a – 15f产品。
• Gold and Palladium Mediated Bimetallic Catalysis: Mechanistic Investigation through the Isolation of the Organogold(I) Intermediates
  作者：Arno Verlee、Thomas Heugebaert、Tom van der Meer、Pavel Kerchev、Kristof Van Hecke、Frank Van Breusegem、Christian V. Stevens

  DOI：10.1021/acscatal.9b02275

  日期：2019.9.6

  catalytic systems are a unique couple due to the carbophilic Lewis acidity of Au and the redox properties of Pd. To gain more insight into this bimetallic couple, a synthetic and mechanistic investigation was conducted. As key substrates, ynamides (N-alkynyl allyloxycarbamates and N-alkynyl ethyloxycarbamates) were used. Essential for the mechanistic part was the isolation of the organogold(I) intermediate

  基于Au-Pd的催化系统是独特的一对，这归因于Au的嗜碳路易斯酸度和Pd的氧化还原特性。为了深入了解这对双金属材料，进行了合成和机械研究。作为关键底物，使用乙酰胺（N-炔基烯丙氧基氨基甲酸酯和N-炔基乙氧基氨基甲酸酯）。机械部分必不可少的是有机金（I）中间体的分离，以验证所提出的机理。总共合成了18个多取代的恶唑酮和12个有机金（I）配合物。
• A Modular Synthesis of 4-Aminoquinolines and [1,3] N-to-C Rearrangement to Quinolin-4-ylmethanesulfonamides
  作者：Kyung Hwan Oh、Jin Gyeong Kim、Jin Kyoon Park

  DOI：10.1021/acs.orglett.7b01701

  日期：2017.8.4

  diversified 4-aminoquinolines using nitriles, diaryliodoniums, and ynamides. The C7-substituted regioisomers were formed regioselectively when meta-substituted phenyliodonium salts were used. [1,3] N-to-C rearrangement of the products to quinolin-4-ylmethanesulfonamides and simultaneous deprotection of benzyl and sulfonamide group were newly developed. Finally, antimalarial CK-2-68 was successfully prepared

  铜催化的区域控制的三组分反应使用腈，二芳基碘鎓和乙酰胺提供了多样化的4-氨基喹啉。当使用间取代的苯基碘鎓盐时，C 7取代的区域异构体是区域选择性地形成的。[1,3]产品的N-C重排为喹啉-4-基甲烷磺酰胺，同时脱保护苄基和磺酰胺基团。最后，成功制备了抗疟药CK-2-68。
• Palladium-Catalyzed Cascade 5-<i>endo</i>-dig Cyclization of Ynamides to Form 4-Alkynyloxazolones
  作者：Tales A. C. Goulart、Davi Fernando Back、Sidnei Moura E. Silva、Gilson Zeni

  DOI：10.1021/acs.joc.1c02978

  日期：2022.3.4

  The selective synthesis of 4-alkynyloxazolones and their further applications as substrates to electrophile-promoted nucleophilic cyclization have been developed. The reaction of ynamides with terminal alkynes proceeded smoothly to give 4-alkynyloxazolones in the presence of a catalytic amount of palladium(II) acetate. The products were obtained with the sequential formation of new C–C and C–O bonds

  已经开发了 4-炔基恶唑酮的选择性合成及其作为底物在亲电促进的亲核环化中的进一步应用。在催化量的乙酸钯 (II) 存在下，炔酰胺与末端炔烃的反应顺利进行，得到 4-炔基恶唑酮。通过级联程序顺序形成新的 C-C 和 C-O 键获得产物。第一步涉及通过 5- endo -dig 闭合形成碳-氧键，结晶样品的 X 射线分析证实了这一点。随后，4-炔基恶唑酮与亲电硒源的反应通过亲电促进的亲核环化得到 3-苯基硒基苯并呋喃衍生物。
• Synthesis of 4-(organoselenyl) oxazolones <i>via</i> cyclization of <i>N</i>-alkynyl ethylcarbamates promoted by organoselenium
  作者：Tales A. C. Goulart、Ana Maria S. Recchi、Davi Fernando Back、Gilson Zeni

  DOI：10.1039/d2ob00682k

  日期：——

  Organoselenyl iodide promoted the intramolecular nucleophilic cyclization of N-alkynyl ethylcarbamates in the synthesis of 4-(organoselenyl) oxazolones.

  有机硒碘化物促进了N-烷基乙氨酸乙酯内环亲核反应，用于合成4-(有机硒基)噁唑酮。