4-乙烯基-3-(4-甲氧基苯基)-1,3-恶唑烷-2-酮 | 115148-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-乙烯基-3-(4-甲氧基苯基)-1,3-恶唑烷-2-酮
• 英文名称: 3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one
• 英文别名: 2-Oxazolidinone, 4-ethenyl-3-(4-methoxyphenyl)-；4-ethenyl-3-(4-methoxyphenyl)-1,3-oxazolidin-2-one
• CAS: 115148-32-8
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: JGSWAJKWOUDRBA-UHFFFAOYSA-N

物化性质

• 沸点：
  331.5±41.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-乙烯基-3-(4-甲氧基苯基)-1,3-恶唑烷-2-酮 在 ammonium cerium(IV) nitrate 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 2-(Boc-氨基)-3-丁醇
  参考文献：
  名称：

  不含其他立体生成单元的螺旋手性聚合物：不对称催化中的新型配体。

  摘要：

  DOI：

  10.1002/1521-3773(20020503)41:9<1614::aid-anie1614>3.0.co;2-5
• 作为产物：
  描述：

  [(E)-4-[(4-methoxyphenyl)carbamoyloxy]but-2-enyl] N-(4-methoxyphenyl)carbamate 在 tris(dibenzylideneacetone)dipalladium (0) 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到4-乙烯基-3-(4-甲氧基苯基)-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  Palladium(0)-catalyzed cyclization of 2-butenylene dicarbamates forming 4-vinyl-2-oxazolidones

  摘要：

  DOI：

  10.1016/s0040-4039(00)96638-3

文献信息

• Formal Aza‐Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis
  作者：Xiangli Yi、Xile Hu

  DOI：10.1002/anie.201814509

  日期：2019.3.26

  In oxidative electrochemical organic synthesis, radical intermediates are often oxidized to cations on the way to final product formation. Herein, we describe an approach to transform electrochemically generated organic radical intermediates into neutral products by reaction with a metal catalyst. This approach combines electrochemical oxidation with Cu catalysis to effect formal aza‐Wacker cyclization

  在氧化电化学有机合成中，自由基中间体通常在最终产物形成的途中被氧化成阳离子。在本文中，我们描述了一种通过与金属催化剂反应将电化学生成的有机自由基中间体转变成中性产物的方法。该方法将电化学氧化与Cu催化结合起来，实现内部烯烃的正式aza-Wacker环化。Cu催化剂对于将仲和伯烷基自由基中间体转化为烯烃是必不可少的。可以在温和条件下制备包括恶唑烷酮，咪唑啉酮，噻唑烷酮，吡咯烷酮和异吲哚啉酮在内的五元N杂环。
• Palladium(0)-Catalyzed Reaction of Acidic Anilines with (Z)-2-Butene-1,4-diyl Dicarbonate – Preparation ofN-Aryl-4-vinyloxazolidin-2-ones
  作者：Marcial Moreno-Mañas、Lurdes Morral、Roser Pleixats、Silvia Villarroya

  DOI：10.1002/(sici)1099-0690(199901)1999:1<181::aid-ejoc181>3.0.co;2-e

  日期：1999.1

  N-aryl-4-vinyloxazolidin-2-ones. The success of the reaction depends on the acidity of the aniline and requires in situ conversion of the dicarbonate into carbamate carbonate by nucleophilic attack of the aniline conjugate base followed by palladium-catalyzed intramolecular cyclization.

  酸性苯胺与（Z）-2-丁烯-1,4-二碳酸二酯的钯催化反应，得到N-芳基-4-乙烯基恶唑烷-2-酮。反应的成功取决于苯胺的酸度，并且需要通过苯胺共轭碱的亲核攻击将二碳酸酯原位转化为氨基甲酸酯碳酸酯，然后进行钯催化的分子内环化反应。
• In situ screening to optimize variables in organic reactions
  申请人：University of Nebraska

  公开号：US20030148257A1

  公开（公告）日：2003-08-07

  A biphasic process for rapid screening of organic reactions comprising monitoring relative rates of parallel organic reactions. The screening process is suitable to determine the efficacy of different reactants, process conditions, and process enhancers such as catalysts or promoters. The biphasic process also allows multiple samples to be analyzed/monitored simultaneously. In addition because enzymes are used to monitor the reaction product in this invention, when that product is chiral and an enantio-discriminating enzyme is used to monitor the product, in addition to the relative rates, enantioselectivities of a set of parallel organic reactions can also be determined. The monitoring is done in situ and thus removal of aliquots for separate testing is unnecessary

  一种用于快速筛选有机反应的双相过程，包括监测并行有机反应的相对速率。该筛选过程适用于确定不同反应物、工艺条件和工艺增强剂（如催化剂或促进剂）的功效。双相过程还允许同时分析/监测多个样品。此外，由于在该发明中使用酶监测反应产物，当该产物是手性的并且使用对映选择酶监测产物时，除了相对速率外，还可以确定一组并行有机反应的对映选择性。监测是在原位进行的，因此不需要取小样进行单独测试。
• In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination
  作者：David B. Berkowitz、Weijun Shen、Gourhari Maiti

  DOI：10.1016/j.tetasy.2004.06.052

  日期：2004.9

  An in situ enzymatic screening (ISES) approach to rapid catalyst evaluation recently pointed to Ni(0) as a new candidate transition metal for intramolecular allylic amination. This led to further exploration of chiral bidentate phosphine ligands for such transformations. Herein, a variety of P,N-ligands are examined for this Ni(0)-chemistry, using a model reaction leading into the vinylglycinol scaffold. On the one hand, an N,N-bis(2-diphenylphosphinoethyl)alkylamine ('PNP') ligand proved to be the fastest ligand yet seen for this Ni(0)-transformation. On the other, phosphinooxazoline (PHOX) ligands of the Pfaltz-Helmchen-Williams variety gave the highest enantioselectivities (up to 51% ee) among P,N-ligands examined. (C) 2004 Elsevier Ltd. All rights reserved.
• HAYASHI, TAMIO;YAMAMOTO, AKIHIRO;ITO, YOSHIHIKO, TETRAHEDRON LETT., 28,(1987) N 41, 4837-4840
  作者：HAYASHI, TAMIO、YAMAMOTO, AKIHIRO、ITO, YOSHIHIKO

  DOI：——

  日期：——