N-phenylhex-5-ynamide | 864936-03-8

• 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-phenylhex-5-ynamide
• 英文别名: 5-Hexynamide, N-phenyl-
• CAS: 864936-03-8
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: JNOYSVJWTMTJEN-UHFFFAOYSA-N

物化性质

• 沸点：
  366.9±25.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-phenylhex-5-ynamide 在 magnesium iodide diethyletherate 、 碘 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到(E)-5,6-diiodo-N-phenylhex-5-enamide
  参考文献：
  名称：

  铜催化的区域选择性分子内N-卤代酰化反应合成环外和环内酰胺

  摘要：

  1,2-二卤代烯烃与酰胺的分子内铜催化交叉偶联反应生成环状β-卤代烯酰胺，后者可参与第二次交叉偶联反应以有效合成高度官能化的环状酰胺。外环和内环区域异构体之间分子内偶联的选择性是至关重要的合成因素，并受底物结构和反应条件的影响。

  DOI：

  10.1002/ejoc.202000137
• 作为产物：
  描述：

  5-己炔酸 在 ammonium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-phenylhex-5-ynamide
  参考文献：
  名称：

  铜催化的区域选择性分子内N-卤代酰化反应合成环外和环内酰胺

  摘要：

  1,2-二卤代烯烃与酰胺的分子内铜催化交叉偶联反应生成环状β-卤代烯酰胺，后者可参与第二次交叉偶联反应以有效合成高度官能化的环状酰胺。外环和内环区域异构体之间分子内偶联的选择性是至关重要的合成因素，并受底物结构和反应条件的影响。

  DOI：

  10.1002/ejoc.202000137

文献信息

• Tandem Nucleophilic Addition/Fragmentation Reactions and Synthetic Versatility of Vinylogous Acyl Triflates
  作者：Shin Kamijo、Gregory B. Dudley

  DOI：10.1021/ja0608085

  日期：2006.5.1

  analysis of the chemistry of vinylogous acyl triflates provides insight into important chemical processes and opens new directions in synthetic technology. Tandem nucleophilic addition/C-C bond cleaving fragmentation reactions of cyclic vinylogous acyl triflates 1 yield a variety of acyclic acetylenic compounds. Full details are disclosed herein. A wide array of nucleophiles, such as organolithium and Grignard

  对乙烯基三氟甲磺酸酯化学的彻底分析提供了对重要化学过程的深入了解，并为合成技术开辟了新的方向。环状乙烯基三氟甲磺酸酯 1 的串联亲核加成/CC 键裂解断裂反应产生多种无环炔属化合物。本文公开了全部细节。应用了多种亲核试剂，例如有机锂和格氏试剂、烯醇锂及其类似物、氢化物试剂和氨基化锂。各自的反应产生酮 2、1,3-二酮及其类似物 3、醇 4 和酰胺 5。本反应建议通过亲核试剂与起始三氟甲磺酸酯 1 的羰基进行 1,2-加成来进行形成四面体醇盐中间体 C，然后进行 Grob 型裂解，其影响 CC 键裂解以产生无环炔属化合物 2-5 和 7。三氟甲磺酸酯部分的有效核疏散性通过 1 的 sigma 键框架引导，提供直接进入断裂途径的途径，而不否认环状乙烯基酯的其他典型反应. 还说明了乙烯基酰基三氟甲磺酸酯的合成多功能性，包括环状烯酮核心 (1 --> 6 或 8) 的官能化反应。
• Process for preparing combinatorial libraries
  申请人：Bayer CropScience GmbH

  公开号：EP1577281A1

  公开（公告）日：2005-09-21

  A process for the production of a combinatorial library of where a plurality of organic molecules is synthesized by chemically fixing a plurality of starting materials each to a separate portion of solid resin, which is combined with a radiofrequency tag, building up the organic molecules in multiple reaction steps, and finally cleaving of the desired organic molecules, where at least one of the multiple reaction steps is carried out under microwave irradiation.

  一种生产组合库的方法，其中通过将多种有机分子合成固定在固体树脂的不同部分上的多种起始材料进行化学固定，该固体树脂结合有射频标签，通过多个反应步骤构建有机分子，并最终裂解所需的有机分子，其中至少一个多个反应步骤在微波辐射下进行。
• Design and synthesis of novel isoxazole-based HDAC inhibitors
  作者：Paola Conti、Lucia Tamborini、Andrea Pinto、Laura Sola、Roberta Ettari、Ciro Mercurio、Carlo De Micheli

  DOI：10.1016/j.ejmech.2010.06.035

  日期：2010.9

  A series of isoxazole-based histone deacetylase (HDAC) inhibitors structurally related to SAHA were designed and synthesized. The isoxazole moiety was inserted in the vicinity of the Zn(2+)-binding group in order to check its participation in the coordinating process. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Amide-Directed Formation of Five-Coordinate Osmium Alkylidenes from Alkynes
  作者：Noelia Casanova、Miguel A. Esteruelas、Moisés Gulías、Carmen Larramona、José L. Mascareñas、Enrique Oñate

  DOI：10.1021/acs.organomet.5b00777

  日期：2016.1.25

  The amide-directed synthesis of five-coordinate osmium alkylidene derivatives from alkynes is reported. These types of complexes, which have been elusive until now because of the tendency of asmium to give hydride alkylidyne species, are prepared by reaction of the dihydride OsH2Cl2((PPr3)-Pr-i)(2) (1) with terminal alkynes containing a distal amide group. Complex 1 reacts with N-phenylhex-5-ynamide and N-phenylhepta-6-ynamide to give OsCl2=C(CH3)(CH2)(n)NH(CO)Phl((PPr3)-Pr-i)(2) (n = 3 (2), 4 (3)). The relative position of carbonyl and NH groups in the organic substrates has no influence on the reaction. Thus, treatment of 1 with N-(pent-4-p-1-yObenzamide leads to OsCl2=C(CH3)(CH2)(3)NHC(O)Ph}((PPr3)-Pr-i)(2) (4). The new compounds are intermediate species in the cleavage of the C-C triple bond of the alkynes. Under mild conditions, they undergo the rupture of the C-alpha-CH3 bond of the alkylidene, which comes from the alkyne triple bond, to afford six-coordinate hydride alkylidyne derivatives. In dichloromethane, complex 2 gives a 10:7 mixture of OsHCl2 C(CH2)(3)C(O)NHPh}((PPr3)-Pr-i)(2) (5) and OsHCl2 CCH(CH3)(CH2)(2)C(O)NHPh}((PPr3)-Pr-i)(2) (6). The first complex contains a linear separation between the alkylidyne C-alpha atom and the amide group, whereas the spacer is branched in the second complex. In contrast to the case for 2, complex 4 selectively affords OsHCl2 C(CH2)(3)NHC(O)Ph}((PPr3)-Pr-i)(2) (7). In spite of their instability, these compounds give the alkylidene allene metathesis, being a useful entry to five-coordinate vinylidene complexes, including the dicarbon-disubstituted OsCl2(=C=CMe2)((PPr3)-Pr-i)(2) (8) and the monosubstituted OsCl2(=C=CHCy)((PPr3)-Pr-i)(2) (9).
• Synthesis of Exo- and Endocyclic Enamides Through Copper-Catalyzed Regioselective Intramolecular <i>N</i> -Halovinylation
  作者：Nicolas Gilbert、Simon Ricard、Jodrey Bergeron、Pierre Lambolez、Benoit Daoust

  DOI：10.1002/ejoc.202000137

  日期：2020.5.10

  copper‐catalyzed cross‐coupling of 1,2‐dihaloalkenes and amides leads to cyclic β‐haloenamides, which can participate in a second cross‐coupling reaction to efficiently synthesize highly functionalized cyclic enamides. The selectivity of the intramolecular coupling between exo‐ and endocyclic regioisomers is a crucial synthetic factor and can be influenced by the structure of the substrate and the reaction conditions

  1,2-二卤代烯烃与酰胺的分子内铜催化交叉偶联反应生成环状β-卤代烯酰胺，后者可参与第二次交叉偶联反应以有效合成高度官能化的环状酰胺。外环和内环区域异构体之间分子内偶联的选择性是至关重要的合成因素，并受底物结构和反应条件的影响。