2'-bromophenyl-(4,4-dimethyl-2-oxazolin-2-yl)ketone | 1194064-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2'-bromophenyl-(4,4-dimethyl-2-oxazolin-2-yl)ketone
• 英文别名: (2-bromophenyl)(4,4-dimethyloxazolinyl)methanone；(2-bromophenyl)-(4,4-dimethyl-5H-1,3-oxazol-2-yl)methanone
• CAS: 1194064-63-5
• 化学式: C₁₂H₁₂BrNO₂
• 分子量: 282.137
• InChiKey: MCCYDDXVGBQKEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-bromophenyl-(4,4-dimethyl-2-oxazolin-2-yl)ketone 在 silica gel 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到3-(2-bromophenyl)-5,5-dimethyl-5,6-dihydro[1,4]oxazin-2-one
  参考文献：
  名称：

  Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective β-lithiation

  摘要：

  The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH(2)OH) or by chloromethylation of 2-acyl-2-oxazolines. The synthetic utility of such oxiranes based on their ability to act either as electrophiles, undergoing ring-opening reactions with nucleophiles, or as nucleophiles in form of the oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated. (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tet.2009.08.040
• 作为产物：
  描述：

  4,4-二甲基-2-氧唑啉 、 2-溴苯甲酰氯 在 正丁基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 乙醚 为溶剂， 反应 0.33h， 以60%的产率得到2'-bromophenyl-(4,4-dimethyl-2-oxazolin-2-yl)ketone
  参考文献：
  名称：

  Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective β-lithiation

  摘要：

  The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH(2)OH) or by chloromethylation of 2-acyl-2-oxazolines. The synthetic utility of such oxiranes based on their ability to act either as electrophiles, undergoing ring-opening reactions with nucleophiles, or as nucleophiles in form of the oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated. (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tet.2009.08.040

文献信息

• Zincation of 4,4-dimethyloxazoline using TMPZnCl·LiCl. A new preparation of 2-aryloxazolines
  作者：Diana Haas、Maximilian S. Hofmayer、Tomke Bresser、Paul Knochel

  DOI：10.1039/c5cc01144b

  日期：——

  4,4-Dimethyloxazoline is directly zincated using TMPZnCl·LiCl and further functionalized by Pd-catalyzed cross-couplings, as well as Cu-mediated acylation and allylation reactions.

  4,4-二甲基恶唑啉直接使用TMPZnCl·LiCl进行锌化，并通过钯催化的交叉偶联反应以及铜介导的酰化和烯丙基化反应进一步官能化。
• Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective β-lithiation
  作者：Leonardo Degennaro、Vito Capriati、Claudia Carlucci、Saverio Florio、Renzo Luisi、Irene Nuzzo、Corrado Cuocci

  DOI：10.1016/j.tet.2009.08.040

  日期：2009.10

  The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH(2)OH) or by chloromethylation of 2-acyl-2-oxazolines. The synthetic utility of such oxiranes based on their ability to act either as electrophiles, undergoing ring-opening reactions with nucleophiles, or as nucleophiles in form of the oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated. (C) 2009 Elsevier Ltd. All rights reserved