2,3,5,6,7,8-hexahydro-3-(1-methyl-2-oxopropyl)-6,8-methano-7,7,8a-trimethyl-5H-1,4-benzoxazin-2-one | 293300-36-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,3,5,6,7,8-hexahydro-3-(1-methyl-2-oxopropyl)-6,8-methano-7,7,8a-trimethyl-5H-1,4-benzoxazin-2-one
• 英文别名: (1R,2R,5R,9R)-2,10,10-trimethyl-5-[(2R)-3-oxobutan-2-yl]-3-oxa-6-azatricyclo[7.1.1.02,7]undec-6-en-4-one
• CAS: 293300-36-4
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: DMHAQEUPWXSTHG-DPTSUGSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,5,6,7,8-hexahydro-3-(1-methyl-2-oxopropyl)-6,8-methano-7,7,8a-trimethyl-5H-1,4-benzoxazin-2-one 在 氢氟酸 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (3R,4R,5R)-4-hydroxyisoleucine lactone hydrofluoride
  参考文献：
  名称：

  Synthesis of enantiomerically pure (3R,4R,5R)-4-hydroxy isoleucine lactone

  摘要：

  A short four-step synthesis of (3R,4R,5R)-4-hydroxyisoleucine lactone with total control of stereochemistry is reported, the key intermediate being the didehydroamino acid derivative arising from an aldol dehydration reaction between a glycine anion equi, lent and butan-2,3-dione. (C) 2001 Published by Elsevier Science.

  DOI：

  10.1016/s0957-4166(01)00465-7
• 作为产物：
  描述：

  (6R,8R,8aR)-7,7,8a-trimethyl-3,5,6,7,8,8a-hexahydro-2H-6,8-methanobenzo[b][1,4]oxazin-2-one 在 base 作用下， 生成 2,3,5,6,7,8-hexahydro-3-(1-methyl-2-oxopropyl)-6,8-methano-7,7,8a-trimethyl-5H-1,4-benzoxazin-2-one
  参考文献：
  名称：

  Two key chiral intermediates in a new 4-hydroxyisoleucine synthesis

  摘要：

  We present the crystal and molecular structure of two key compounds of a new synthesis strategy for isomers of natural (2S,3R,4S)-4-hydroxyisoleucines, 2,3,5,6,7,8-hexahydro-3-(1-hydroxy-1-methyl-2-oxopropyl)-6,8-methano-7,7,8a-trimethyl-5H-1,4-benzoxazin-2-one, C16H23NO4, and 2,3,5,6,7,8-hexahydro-3-(1-methyl-2-oxopropyl)-6,8-methano-7,7,8a-trimethyl-5H-1,4-benzoxazin-2-one, C16H23NO3. A new optically pure chiral oxazinone auxiliary derived from (1R,2R,5R)-2-hydroxypinan-3-one was used.

  DOI：

  10.1107/s010827010000740x