2-tert-pentyl-4,4-dimethyl-4,5-dihydrooxazole | 130287-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-tert-pentyl-4,4-dimethyl-4,5-dihydrooxazole
• 英文别名: 4,4-dimethyl-2-(2-methylbutan-2-yl)-5H-1,3-oxazole
• CAS: 130287-75-1
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: MBDAGVWLXIYQOH-UHFFFAOYSA-N

物化性质

• 沸点：
  197.5±9.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-tert-pentyl-4,4-dimethyl-4,5-dihydrooxazole 在 palladium diacetate 碘苯二乙酸 、 硫酸 、 碘 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 苯 为溶剂， 反应 41.0h， 生成 1-乙基环丙烷-1-羧酸
  参考文献：
  名称：

  Converting gem-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential C−H Activation and Radical Cyclization

  摘要：

  A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

  DOI：

  10.1021/ol0618858
• 作为产物：
  描述：

  2,2-二甲基丁酸 在 草酰氯 、 三苯基膦 作用下， 生成 2-tert-pentyl-4,4-dimethyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Converting gem-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential C−H Activation and Radical Cyclization

  摘要：

  A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

  DOI：

  10.1021/ol0618858

文献信息

• [EN] CATALYTICS ASYMMETRIC ACTIVATION OF UNACTIVATED C-H BONDS, AND COMPOUNDS RELATED THERETO<br/>[FR] ACTIVATION CATALYTIQUE ASYMETRIQUE DE LIAISONS C-H INACTIVEES ET COMPOSES ASSOCIES
  申请人：UNIV BRANDEIS

  公开号：WO2006026053A1

  公开（公告）日：2006-03-09

  One aspect of the present invention is directed in part to catalytic and stereoselective functionalization of unactivated C-H bonds of simple organic substrates. The compounds and methods provided herein allow one to control the stereochemistry in a C-H activation step, activate substrates containing α-hydrogens next to the directing group, and remove a directing group under mild conditions. One aspect of the present invention relates to a transition-metal-catalyzed method for selective and asymmetric oxidation of carbons located in a β- or Ϝ-position relative to an auxiliary. Another aspect of the invention relates to the enantiomerically-enriched substrates and the enantiomerically-enriched products formed via said method. In certain embodiments, oxazoline and oxazinone directing groups are used. In addition, the Boc protecting group has been identified as a directing group which does not necessitate removal.

  本发明的一个方面部分涉及简单有机底物中未活化C-H键的催化和对映选择性官能团化。本发明提供的化合物和方法允许在C-H活化步骤中控制立体化学，活化含有邻近导向基团的α-氢的底物，并在温和条件下移除导向基团。本发明的另一方面涉及一种过渡金属催化的方法，用于选择性和非对称氧化位于辅助基团β-或Ϝ-位置上的碳。发明的另一个方面涉及通过所述方法形成的对映体富集的底物和对映体富集的产品。在某些实施例中，使用了恶唑啉和恶嗪酮导向基团。此外，Boc保护基团被识别为不需要移除的导向基团。
• Cyclopalladated 2-t-butyl-4,4-dimethyl-2-oxazoline: its preparation, and use in the functionalisation of a non-activated carbon-hydrogen bond
  作者：G. Balavoine、J.C. Clinet

  DOI：10.1016/0022-328x(90)85112-c

  日期：1990.7

  Activation and functionalisation of one of the methyl groups of pivalic acid can be achieved through cyclopalladation of its 4,4-dimethyloxazoline derivative. This reaction gives a separable mixture of dinuclear and trinuclear species. The dimeric complex undergoes insertion of methyl vinyl ketone and of carbon monoxide, but is alkylated by aliphatic iodides, thereby providing a new route to homologated

  新戊酸的甲基之一的活化和官能化可通过其4，4-二甲基恶唑啉衍生物的环钯反应实现。该反应得到双核和三核物质的可分离混合物。该二聚配合物经历了甲基乙烯基酮和一氧化碳的插入，但是被脂肪族碘化物烷基化，从而提供了新的途径来合成均化的叔羧酸。
• Pd-Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic CH Bond Oxidation
  作者：Ramesh Giri、Jue Liang、Jian-Guang Lei、Jiao-Jie Li、Dong-Hui Wang、Xiao Chen、Isaac Clement Naggar、Chengyun Guo、Bruce M. Foxman、Jin-Quan Yu

  DOI：10.1002/anie.200502767

  日期：2005.11.18
• Converting <i>gem</i>-Dimethyl Groups into Cyclopropanes via Pd-Catalyzed Sequential C−H Activation and Radical Cyclization
  作者：Ramesh Giri、Masayuki Wasa、Steven P. Breazzano、Jin-Quan Yu

  DOI：10.1021/ol0618858

  日期：2006.12.1

  A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl)dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.