(-)-(1S,4S,6R,8R)-[11,11-Dimethyl-5-(4-\ tolylsulfonyl)-3-oxa-5-azatricyclo[6.2.1.0^1,6^]undec-4-yl](phenyl)methanone | 1076209-23-8

• 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: (-)-(1S,4S,6R,8R)-[11,11-Dimethyl-5-(4-\ tolylsulfonyl)-3-oxa-5-azatricyclo[6.2.1.0^1,6^]undec-4-yl](phenyl)methanone
• 英文别名: [(1S,4S,6R,8R)-11,11-dimethyl-5-(4-methylphenyl)sulfonyl-3-oxa-5-azatricyclo[6.2.1.01,6]undecan-4-yl]-phenylmethanone
• CAS: 1076209-23-8
• 化学式: C₂₅H₂₉NO₄S
• 分子量: 439.576
• InChiKey: OBRKMAQXPPDQEP-YAYWFPAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(1S,4S,6R,8R)-[11,11-Dimethyl-5-(4-\ tolylsulfonyl)-3-oxa-5-azatricyclo[6.2.1.0^1,6^]undec-4-yl](phenyl)methanone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以90%的产率得到(R)-[(1S,4S,6R,8R)-11,11-dimethyl-5-(4-methylphenyl)sulfonyl-3-oxa-5-azatricyclo[6.2.1.01,6]undecan-4-yl]-phenylmethanol
  参考文献：
  名称：

  Diastereoselective Reduction of Chiral N-Tosyl-2-benzoyl-1,3-oxazine Derived from (1R)-(+)-Camphor

  摘要：

  The stereochemistry of reduction of chiral N-tosyl-2-benzoyl-1,3-oxazine prepared by condensation of 1,3-amino alcohol derived from (1R)-(+)-camphor with phenylglyoxal was investigated using various reducing agents. Based on X-ray crystallography, 2-benzoyl group in 1,3-oxazine ring was situated in the axial position. High diastereoselectivity observed in the hydride reduction can be explained by a chelate model where N-tosyl oxygen atom takes part in chelation rather than ring oxygen atom.

  DOI：

  10.3987/com-10-12016
• 作为产物：
  描述：

  (1S,2R)-1-(hydroxymethyl)-2-amino-7,7-dimethyl-bicyclo<2.2.1>heptane 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 水 、 乙酸乙酯 、 苯 为溶剂， 反应 30.5h， 生成 (-)-(1S,4S,6R,8R)-[11,11-Dimethyl-5-(4-\ tolylsulfonyl)-3-oxa-5-azatricyclo[6.2.1.0^1,6^]undec-4-yl](phenyl)methanone 、
  参考文献：
  名称：

  Diastereoselective Reduction of Chiral N-Tosyl-2-benzoyl-1,3-oxazine Derived from (1R)-(+)-Camphor

  摘要：

  The stereochemistry of reduction of chiral N-tosyl-2-benzoyl-1,3-oxazine prepared by condensation of 1,3-amino alcohol derived from (1R)-(+)-camphor with phenylglyoxal was investigated using various reducing agents. Based on X-ray crystallography, 2-benzoyl group in 1,3-oxazine ring was situated in the axial position. High diastereoselectivity observed in the hydride reduction can be explained by a chelate model where N-tosyl oxygen atom takes part in chelation rather than ring oxygen atom.

  DOI：

  10.3987/com-10-12016

文献信息

• Diastereoselective Reduction of Chiral N-Tosyl-2-benzoyl-1,3-oxazine Derived from (1R)-(+)-Camphor
  作者：Kwang-Youn Ko、Hoseop Yun

  DOI：10.3987/com-10-12016

  日期：——

  The stereochemistry of reduction of chiral N-tosyl-2-benzoyl-1,3-oxazine prepared by condensation of 1,3-amino alcohol derived from (1R)-(+)-camphor with phenylglyoxal was investigated using various reducing agents. Based on X-ray crystallography, 2-benzoyl group in 1,3-oxazine ring was situated in the axial position. High diastereoselectivity observed in the hydride reduction can be explained by a chelate model where N-tosyl oxygen atom takes part in chelation rather than ring oxygen atom.