(1S,6R,8S)-11,11-dimethyl-3-propanoyl-5-oxa-3-azatricyclo[6.2.1.01,6]undecan-4-one | 192575-96-5

• 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: (1S,6R,8S)-11,11-dimethyl-3-propanoyl-5-oxa-3-azatricyclo[6.2.1.01,6]undecan-4-one
• CAS: 192575-96-5
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: PRTBMXPIBFMWSM-RBZYPMLTSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  386.7±11.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (1S,6R,8S)-11,11-dimethyl-3-propanoyl-5-oxa-3-azatricyclo[6.2.1.01,6]undecan-4-one 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 生成 (1S,6R,8S)-3-[(2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoyl]-11,11-dimethyl-5-oxa-3-azatricyclo[6.2.1.01,6]undecan-4-one
  参考文献：
  名称：

  Intramolecular ring cleavage of chiral terpenoid-derived oxazinone via asymmetric anti-aldol reaction: Unexpected entry to a N-substituted tetrahydro-1,3-oxazine-2,4-dione derivative

  摘要：

  In the presence of excess Bu2BOTf to promote anti-selectivity, an asymmetric aldol reaction with a homochiral terpenoid-derived 1,3-oxazin-2-one as the chiral control element results unexpectedly in ring cleavage by an intramolecular process to form a N-substituted tetrahydro-1,3-oxazine-2,4-dione in virtually quantitative yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01058-7
• 作为产物：
  描述：

  丙酰氯 、 ((6S)-endo)-3-aza-11,11-dimethyl-5-oxatricyclo[6.2.1.0^1,6]undecan-4-one 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,6R,8S)-11,11-dimethyl-3-propanoyl-5-oxa-3-azatricyclo[6.2.1.01,6]undecan-4-one
  参考文献：
  名称：

  Intramolecular ring cleavage of chiral terpenoid-derived oxazinone via asymmetric anti-aldol reaction: Unexpected entry to a N-substituted tetrahydro-1,3-oxazine-2,4-dione derivative

  摘要：

  In the presence of excess Bu2BOTf to promote anti-selectivity, an asymmetric aldol reaction with a homochiral terpenoid-derived 1,3-oxazin-2-one as the chiral control element results unexpectedly in ring cleavage by an intramolecular process to form a N-substituted tetrahydro-1,3-oxazine-2,4-dione in virtually quantitative yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01058-7

文献信息

• Intramolecular ring cleavage of chiral terpenoid-derived oxazinone via asymmetric anti-aldol reaction: Unexpected entry to a N-substituted tetrahydro-1,3-oxazine-2,4-dione derivative
  作者：Tariq R Abbas、J.I.G Cadogan、Allan A Doyle、Ian Gosney、Philip K.G Hodgson、Garnet E Howells、Alison N Hulme、Simon Parsons、Ian H Sadler

  DOI：10.1016/s0040-4039(97)01058-7

  日期：1997.7

  In the presence of excess Bu2BOTf to promote anti-selectivity, an asymmetric aldol reaction with a homochiral terpenoid-derived 1,3-oxazin-2-one as the chiral control element results unexpectedly in ring cleavage by an intramolecular process to form a N-substituted tetrahydro-1,3-oxazine-2,4-dione in virtually quantitative yield. (C) 1997 Elsevier Science Ltd.