N-(2-chloroethyl)-4,5-diphenyl-4-oxazolin-2-one | 148715-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-chloroethyl)-4,5-diphenyl-4-oxazolin-2-one
• 英文别名: 3-(2-chloroethyl)-4,5-diphenyloxazol-2(3H)-one；3-(2-chloroethyl)-4,5-diphenyl-2(3H)oxazolone；3-(2-Chloroethyl)-4,5-diphenyl-1,3-oxazol-2-one
• CAS: 148715-44-0
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: JBLMHWNGQKVRCN-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  435.9±55.0 °C(Predicted)
• 密度：
  1.364 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  N-(2-chloroethyl)-4,5-diphenyl-4-oxazolin-2-one 在 palladium diacetate potassium tert-butylate 、 四丁基氯化铵 、 碳酸氢钠 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 52.5h， 生成 3-<(E)-<2-(2-fluorophenyl)ethenyl>>-4,5-diphenyl-2(3H)oxazolone
  参考文献：
  名称：

  Phenethylamines via Heck arylation of a new vinylamine equivalent

  摘要：

  A new vinylamine equivalent, N-vinyloxazolone 3, has been prepared in three steps and shown to undergo Heck arylation with a variety of substrates. The Heck adducts thus obtained are then converted in one step and high yield to phenethylamine hydrochlorides. As a general synthetic method for preparation of substituted phenethylamines, use of this new reagent is shown to be superior to N-vinylphthalimide in number of steps, regiospecificity, and chemical yield.

  DOI：

  10.1021/jo00064a015
• 作为产物：
  描述：

  4,5-二苯基-1,3-二氧戊环烯-2-酮 、 2-氯乙胺盐酸盐 在 碳酸氢钠 、 三氟乙酸 作用下， 生成 N-(2-chloroethyl)-4,5-diphenyl-4-oxazolin-2-one
  参考文献：
  名称：

  Phenethylamines via Heck arylation of a new vinylamine equivalent

  摘要：

  A new vinylamine equivalent, N-vinyloxazolone 3, has been prepared in three steps and shown to undergo Heck arylation with a variety of substrates. The Heck adducts thus obtained are then converted in one step and high yield to phenethylamine hydrochlorides. As a general synthetic method for preparation of substituted phenethylamines, use of this new reagent is shown to be superior to N-vinylphthalimide in number of steps, regiospecificity, and chemical yield.

  DOI：

  10.1021/jo00064a015

文献信息

• Synthesis and antifungal activity of novel oxazolidin-2-one-linked 1,2,3-triazole derivatives
  作者：Alejandra Ramírez-Villalva、Davir González-Calderón、Roxana I. Rojas-García、Carlos González-Romero、Joaquín Tamaríz-Mascarúa、Macario Morales-Rodríguez、Nieves Zavala-Segovia、Aydeé Fuentes-Benítes

  DOI：10.1039/c7md00442g

  日期：——

  Novel oxazolidin-2-one-linked 1,2,3-triazole derivatives (4a–k) were synthesized by straightforward and versatile azide–enolate (3 + 2) cycloaddition. The series of compounds was screened for antifungal activity against four filamentous fungi as well as six yeast species of Candida spp. According to their efficiency and breadth of scope, they can be ordered as 4k > 4d > 4h > 4a, especially in relation

  通过直接和通用的叠氮化物-烯酸酯（3 + 2）环加成反应合成了新型恶唑烷-2-酮连接的1,2,3-三唑衍生物（4a–k）。筛选了该系列化合物对四种丝状真菌和六种假丝酵母菌的抗真菌活性。根据它们的效率和范围广度，它们可以被排序为4K > 4D > 4H >图4A，特别是在相对于所述活动对显示光滑念珠菌ATCC-34138，皮状丝孢ATCC-28592和冻土毛霉ATCC-8690，即化合物4D，4h和4k显示出优异的抗光滑毛线虫的活性（分别为MIC 0.12、0.25和0.12μgmL -1），优于伊曲康唑（MIC 1μgml -1）。化合物4d（MIC = 2μgmL -1）的活性高于标准抗真菌药物（MIC = 8μgmL -1）对角皮癣菌的活性，而化合物4k表现出优异的抗毛孔霉菌（MIC）的抗霉菌活性。= 2μgmL -1 和4μgmL -1对于伊曲康唑）。另外，我们在本文中描述了一种新颖
• A Single-Step Synthesis of 4-Oxazolin-2-ones and Their Use in the Construction of Polycyclic Structures Bearing Quaternary Stereocenters
  作者：Blanca M. Santoyo、Carlos González-Romero、Omar Merino、Rafael Martínez-Palou、Aydeé Fuentes-Benites、Hugo A. Jiménez-Vázquez、Francisco Delgado、Joaquín Tamariz

  DOI：10.1002/ejoc.200900114

  日期：2009.5

  for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of α-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity

  报道了一种通过 α-酮醇和异氰酸酯的一锅 MW 促进缩合合成 4-恶唑啉-2-酮的新方法。还描述了使用相同起始材料的替代热方法。这些环状烯酰胺是有效的亲核试剂，可与迈克尔受体和异戊二烯基溴反应，得到各种带有一个或两个四元立体中心的多环结构。产物的选择性取决于反应条件和所用的亲电试剂。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Busacca Carl A., Johnson Robert E., Swestock John, J. Org. Chem, 58 (1993) N 12, S 3299-3303
  作者：Busacca Carl A., Johnson Robert E., Swestock John

  DOI：——

  日期：——
• Phenethylamines via Heck arylation of a new vinylamine equivalent
  作者：Carl A. Busacca、Robert E. Johnson、John Swestock

  DOI：10.1021/jo00064a015

  日期：1993.6

  A new vinylamine equivalent, N-vinyloxazolone 3, has been prepared in three steps and shown to undergo Heck arylation with a variety of substrates. The Heck adducts thus obtained are then converted in one step and high yield to phenethylamine hydrochlorides. As a general synthetic method for preparation of substituted phenethylamines, use of this new reagent is shown to be superior to N-vinylphthalimide in number of steps, regiospecificity, and chemical yield.