1-(3-chloroacryloyl)-2-oxazolidinone | 165275-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-(3-chloroacryloyl)-2-oxazolidinone
• 英文别名: 3-[(E)-3-chloroprop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 165275-74-1
• 化学式: C₆H₆ClNO₃
• 分子量: 175.572
• InChiKey: LCDOKTZKBLKQTB-OWOJBTEDSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  223.8±42.0 °C(Predicted)
• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-chloroacryloyl)-2-oxazolidinone 在 N-甲基吗啉 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 4-fluorobenzoic acid endo-3-(2-oxo-oxazolidine-3-carbonyl)-bicyclo[2.2.1]hept-5-en-2-yl ester
  参考文献：
  名称：

  Enantioselective Diels–Alder reactions of 3-(acyloxy)acrylates

  摘要：

  Diels-Alder reactions with 3-(acyloxy)acrylates using chiral Lewis acid catalysts have been successfully carried out. These reactions proceed with high enantioselectivity when a chiral Lewis acid derived from Cu(OTf)(2) and a bisoxazoline is used. The facility of the reaction is dependent on the nature of the acyloxy group in the dienophile. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.090
• 作为产物：
  描述：

  2-唑烷酮 、 (E)-3-Chloroacryloyl chloride 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 以6.11 g的产率得到1-(3-chloroacryloyl)-2-oxazolidinone
  参考文献：
  名称：

  Enantioselective Diels–Alder reactions of 3-(acyloxy)acrylates

  摘要：

  Diels-Alder reactions with 3-(acyloxy)acrylates using chiral Lewis acid catalysts have been successfully carried out. These reactions proceed with high enantioselectivity when a chiral Lewis acid derived from Cu(OTf)(2) and a bisoxazoline is used. The facility of the reaction is dependent on the nature of the acyloxy group in the dienophile. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.090

文献信息

• Chiral Bis(oxazoline)copper(II) Complexes as Lewis Acid Catalysts for the Enantioselective Diels−Alder Reaction
  作者：David A. Evans、Scott J. Miller、Thomas Lectka、Peter von Matt

  DOI：10.1021/ja991190k

  日期：1999.8.1

  Bis(oxazoline)copper(II) complexes are highly enantioselective catalysts in Diels−Alder reactions involving bidentate dienophiles. Cationic [Cu((S,S)-t-Bu-box)]X2 complexes with different counterions have been used as catalysts, revealing a profound influence of the counterion on the rate and stereoselectivity of the catalyst. A square-planar catalyst−substrate complex is proposed to account for the

  双（恶唑啉）铜（II）配合物是涉及双齿亲二烯体的 Diels-Alder 反应中的高度对映选择性催化剂。具有不同抗衡离子的阳离子 [Cu((S,S)-t-Bu-box)]X2 配合物已被用作催化剂，揭示了抗衡离子对催化剂的速率和立体选择性的深远影响。提出了方形平面催化剂 - 底物复合物来解释观察到的高非对映选择性和对映选择性。已获得支持该模型的三个双（恶唑啉）-Cu（II）X 射线结构。使用手性亲二烯体进行的双立体分化实验提供的结果与所提出的方形平面过渡态组合完全一致。除了基于酰亚胺的底物，α、β-不饱和噻唑烷-2-硫酮作为一类具有增强反应性的新型亲二烯体被引入。进行动力学实验以量化产物抑制在反应过程中所起的作用。率和均衡...
• A New Class of Modular Chiral Ligands with Fluxional Groups
  作者：Mukund P. Sibi、Ruzhou Zhang、Shankar Manyem

  DOI：10.1021/ja035979d

  日期：2003.8.1

  In ligand design for asymmetric catalysis, the usual norm is to derive the face shielding elements from a chiral source. New ligands in which the face shielding is determined by fluxional groups are introduced. Their design, modular synthesis, and experiments to demonstrate the significance of the fluxional groups are discussed. The advantage is that the fluxional groups, introduced at a later stage, allow for simple tuning of the face shielding group.
• Evans, David A.; Murry, Jerry A.; Matt, Peter von, Angewandte Chemie, 1995, vol. 107, # 7, p. 864 - 867
  作者：Evans, David A.、Murry, Jerry A.、Matt, Peter von、Norcross, Roger D.、Miller, Scott J.

  DOI：——

  日期：——
• Enantioselective Diels–Alder reactions of 3-(acyloxy)acrylates
  作者：Mukund P. Sibi、Hirofumi Matsunaga

  DOI：10.1016/j.tetlet.2004.05.090

  日期：2004.7

  Diels-Alder reactions with 3-(acyloxy)acrylates using chiral Lewis acid catalysts have been successfully carried out. These reactions proceed with high enantioselectivity when a chiral Lewis acid derived from Cu(OTf)(2) and a bisoxazoline is used. The facility of the reaction is dependent on the nature of the acyloxy group in the dienophile. (C) 2004 Elsevier Ltd. All rights reserved.