3-(3,4-dimethyl-cyclohex-3-enecarbonyl)-oxazolidin-2-one

• 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: 3-(3,4-dimethyl-cyclohex-3-enecarbonyl)-oxazolidin-2-one
• 英文别名: 3-(3,4-Dimethylcyclohex-3-ene-1-carbonyl)-1,3-oxazolidin-2-one
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: NIMBYAREAAJLJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 3-丙烯酰基-2-唑烷酮 在 4,4'-dihydroxy-2,2'-bipyridine-based dendritic Cu complex 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到3-(3,4-dimethyl-cyclohex-3-enecarbonyl)-oxazolidin-2-one
  参考文献：
  名称：

  新型树枝状2,2'-联吡啶配体的合成及其在路易斯酸催化的Diels-Alder和三组分缩合反应中的应用

  摘要：

  通过将4,4'-二羟基-2,2'-联吡啶与聚（芳基醚）树枝状分子偶联，合成了一系列具有2,2'-联吡啶核的树枝状配体。相应的树枝状Cu（OTf）2催化剂用于Diels-Alder和三组分缩合反应。树枝状的Cu（OTf）2催化的Diels-Alder反应进展顺利，这些树枝状的催化剂可以循环使用而不会因再沉淀而失活。三组分缩合反应（例如曼尼希型反应）不仅在二氯甲烷中进行，而且还在水中进行。此外，在Diels-Alder反应和水介质三组分缩合反应中均观察到对化学收率的积极树突作用。

  DOI：

  10.1021/jo070767a

文献信息

• An Air Stable Moisture Resistant Titanium Triflate Complex as a Lewis Acid Catalyst for CC Bond Forming Reactions
  作者：Steven D. Bull、Matthew G. Davidson、Andrew L. Johnson、Mary F. Mahon、Diane E. J. E. Robinson

  DOI：10.1002/asia.200900305

  日期：2010.3.1

  An air and moisture stable C3‐symmetric titanium(IV) triflate, supported by a tripodal amine‐(tris‐phenolate) ligand, has been synthesized and characterized by X‐ray crystallography and shown to be a good Lewis acid catalyst for a range of aza‐Diels–Alder, Diels–Alder, syn aldol, allylation, and alkylation reactions.

  由X射线晶体学合成并表征了一种空气和湿气稳定的C 3对称的三氟甲磺酸三氟甲磺酸钛（IV），并通过X射线晶体学对其进行了表征，显示出在一定范围内是很好的路易斯酸催化剂的氮杂-Diels-桤木，狄尔斯-阿德耳，顺式羟醛，烯丙基化，和烷基化反应。
• Scandium trifluoromethanesulfonate (Sc(OTf)3). A novel reusable catalyst in the Diels-Alder reaction
  作者：Shū Kobayashi、Iwao Hachiya、Mitsuharu Araki、Haruro Ishitani

  DOI：10.1016/s0040-4039(00)79220-3

  日期：1993.6

  Scandium trifluoromethanesulfonate (Sc(OTf)3) is found to be quite effective as a Lewis acid catalyst in the Diels-Alder reaction. The novel catalyst is available in both aqueous and organic media, is easily recovered from aqueous layer after the reaction is completed, and can be reused.

  发现三氟甲磺酸dium（Sc（OTf）3）在Diels-Alder反应中作为路易斯酸催化剂非常有效。该新型催化剂可在水性和有机介质中使用，反应完成后很容易从水层中回收，并可以重复使用。
• Diels–Alder reaction using a dendritic copper(II) triflate-catalyst: a positive dendritic effect on the chemical yield
  作者：Ken-ichi Fujita、Takahito Muraki、Hatsuhiko Hattori、Toshiyasu Sakakura

  DOI：10.1016/j.tetlet.2006.05.040

  日期：2006.7

  A series of dendritic ligands with a 2,2'-bipyridine core was synthesized through the coupling of 4,4'-dihydroxy-2,2'-bipyridine with poly(arylether) dendron in fair yields. The corresponding copper(II) trifluoromethanesulfonate (triflate) dendrimers were applied as a Lewis acid catalyst to the Diels-Alder reaction. A positive dendritic effect on the chemical yields of adducts was observed. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.