2-(1-chloro-2-methylpropan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole | 553650-41-2

• 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-(1-chloro-2-methylpropan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole
• 英文别名: 2-(1,1-Dimethyl-2-chloroethyl)-4,4-dimethyl-2-oxazoline；2-(1-chloro-2-methylpropan-2-yl)-4,4-dimethyl-5H-1,3-oxazole
• CAS: 553650-41-2
• 化学式: C₉H₁₆ClNO
• 分子量: 189.685
• InChiKey: MOBRUOREJAVWQU-UHFFFAOYSA-N

物化性质

• 沸点：
  218.5±23.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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-(1-chloro-2-methylpropan-2-yl)-4,4-dimethyl-4,5-dihydrooxazole 在 palladium diacetate 碘苯二乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以70%的产率得到2-(1-chloro-3-iodo-2-(iodomethyl)propan-2-yl)-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
• 作为产物：
  描述：

  3-氯-2,2-二甲基丙酸 在 氯化亚砜 、 三苯基膦 作用下， 生成 2-(1-chloro-2-methylpropan-2-yl)-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。
• Preparation of low hysteresis rubber by reacting a lithium polymer with oxazoline compounds
  申请人：——

  公开号：US20030125477A1

  公开（公告）日：2003-07-03

  The present invention provides a method of forming a functionalized polymer. The method includes the steps of providing a living lithium polymer and terminating the polymer with an oxazoline compound selected from an organic halide oxazoline and a branched or unbranched vinyl oxazoline compound. The present invention also provides a compounded rubber article wherein carbon black is compounded with a terminated rubber that is the reaction product of a living lithium polymer and such oxazoline compounds.

  本发明提供了一种形成功能化聚合物的方法。该方法包括以下步骤：提供一种活性锂聚合物，并用有机卤代氧唑和分支或非分支乙烯基氧唑化合物中选择的氧唑化合物终止聚合物。本发明还提供了一种混合橡胶制品，其中碳黑与终止聚合物混合，该终止聚合物是活性锂聚合物和上述氧唑化合物的反应产物。
• 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
• US6596798B1
  申请人：——

  公开号：US6596798B1

  公开（公告）日：2003-07-22
• 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.