(4R,5S,6R)-3-(2-bromoacetyl)-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazinan-2-one | 911036-68-5

• 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: (4R,5S,6R)-3-(2-bromoacetyl)-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazinan-2-one
• 英文别名: (5S,6R)-3-(2-bromoacetyl)-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one
• CAS: 911036-68-5
• 化学式: C₁₃H₁₅BrN₂O₃
• 分子量: 327.178
• InChiKey: LNIVLMZGWYPPKQ-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R)-3-(2-bromoacetyl)-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazinan-2-one 在 重水 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以82%的产率得到(4R,5S,6R)-3-(2-bromo-2-deuterioacetyl)-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazinan-2-one
  参考文献：
  名称：

  Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones

  摘要：

  Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric alpha-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good. The ephedrine based aldol adducts were hydrolyzed to afford the alpha-bromo-beta-hydroxycarboxylic acids. The absolute stereochemistry and enantiomeric purity of these products were determined by chiral HPLC and specific rotation measurements. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.036
• 作为产物：
  描述：

  在 lithium hydride 作用下， 以 正己烷 、 1,2-二氯乙烷 为溶剂， 生成 (4R,5S,6R)-3-(2-bromoacetyl)-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazinan-2-one
  参考文献：
  名称：

  Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones

  摘要：

  Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric alpha-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good. The ephedrine based aldol adducts were hydrolyzed to afford the alpha-bromo-beta-hydroxycarboxylic acids. The absolute stereochemistry and enantiomeric purity of these products were determined by chiral HPLC and specific rotation measurements. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.036

文献信息

• Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones
  作者：Trisha R. Hoover、Jonathan A. Groeper、Raleigh W. Parrott、Seshanand P. Chandrashekar、Jennifer M. Finefield、Alexandro Dominguez、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2006.06.036

  日期：2006.7

  Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric alpha-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good. The ephedrine based aldol adducts were hydrolyzed to afford the alpha-bromo-beta-hydroxycarboxylic acids. The absolute stereochemistry and enantiomeric purity of these products were determined by chiral HPLC and specific rotation measurements. (c) 2006 Elsevier Ltd. All rights reserved.