[4-(4-methoxyphenyl)-6,6-dimethyl-5,6-dihydro-4H-1,2-oxazin-3-yl]methanol | 1198015-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [4-(4-methoxyphenyl)-6,6-dimethyl-5,6-dihydro-4H-1,2-oxazin-3-yl]methanol
• 英文别名: [4-(4-Methoxyphenyl)-6,6-dimethyl-4,5-dihydrooxazin-3-yl]methanol；[4-(4-methoxyphenyl)-6,6-dimethyl-4,5-dihydrooxazin-3-yl]methanol
• CAS: 1198015-27-8
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: XZRCVWQRPHJYGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-(4-methoxyphenyl)-6,6-dimethyl-5,6-dihydro-4H-1,2-oxazin-3-yl]methanol 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 以67%的产率得到rel-[(3R,4S)-4-(4-methoxyphenyl)-6,6-dimethyl-1,2-oxazinan-3-yl]methanol
  参考文献：
  名称：

  Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxa­zines

  摘要：

  A new strategy for the synthesis of 2-(1-hydroxyalkyl)pyrrolidines and 2-amino-1,5-diols is suggested. The target compounds can be obtained in high yields from available precursors through the intermediacy of six-membered cyclic nitronates and their rearrangement products. Successive reduction of the latter led to the target products with moderate to high diastereoselectivity.

  DOI：

  10.1055/s-0031-1290973
• 作为产物：
  描述：

  4-(4-methoxyphenyl)-6,6-dimethyl-3-methylene-2-(trimethylsiloxy)-1,2-oxazinane 、 三氟乙酸酐 在 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到[4-(4-methoxyphenyl)-6,6-dimethyl-5,6-dihydro-4H-1,2-oxazin-3-yl]methanol
  参考文献：
  名称：

  N，N-二氧化烯胺与羧酸和磺酸酐的反应 α-羟基肟衍生物合成的新方法

  摘要：

  研究了N，N-二氧化烯胺与羧酸酐和磺酸酐的反应。描述了一种通过N，N-二氧化烯胺与三氟乙酸酐反应合成α-羟基肟衍生物的新方法。 1,2-恶嗪-三氟乙酸酐-羟基肟-烯胺-重排

  DOI：

  10.1055/s-0029-1216907

文献信息

• Reaction of N,N-Dioxyenamines with Anhydrides of Carboxylic and Sulfonic Acids; A New Method for the Synthesis of α-Hydroxyoxime Derivatives
  作者：Alexey Lesiv、Andrey Tabolin、Sema Ioffe

  DOI：10.1055/s-0029-1216907

  日期：2009.9

  The reactions of N,N-dioxyenamines with carboxylic and sulfonic acid anhydrides were investigated. A new method for the synthesis of α-hydroxyoxime derivatives via the reaction of N,N-dioxyenamines with trifluoroacetic anhydride is described. 1,2-oxazine - trifluoroacetic anhydride - hydroxyoxime - enamine - rearrangement

  研究了N，N-二氧化烯胺与羧酸酐和磺酸酐的反应。描述了一种通过N，N-二氧化烯胺与三氟乙酸酐反应合成α-羟基肟衍生物的新方法。 1,2-恶嗪-三氟乙酸酐-羟基肟-烯胺-重排
• Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxa­zines
  作者：Andrey Tabolin、Sema Ioffe、Alexey Lesiv、Yulia Khomutova

  DOI：10.1055/s-0031-1290973

  日期：2012.6

  A new strategy for the synthesis of 2-(1-hydroxyalkyl)pyrrolidines and 2-amino-1,5-diols is suggested. The target compounds can be obtained in high yields from available precursors through the intermediacy of six-membered cyclic nitronates and their rearrangement products. Successive reduction of the latter led to the target products with moderate to high diastereoselectivity.