(2S,2aR,6R,8aS,8bR)-6-Phenyl-2-trimethylsilanylmethyl-octahydro-1,8-dioxa-5a-aza-acenaphthylene | 213685-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2S,2aR,6R,8aS,8bR)-6-Phenyl-2-trimethylsilanylmethyl-octahydro-1,8-dioxa-5a-aza-acenaphthylene
• 英文别名: trimethyl-[[(1S,3S,4R,9R,12R)-9-phenyl-2,11-dioxa-8-azatricyclo[6.3.1.04,12]dodecan-3-yl]methyl]silane
• CAS: 213685-91-7
• 化学式: C₁₉H₂₉NO₂Si
• 分子量: 331.53
• InChiKey: UQCKJROMTGDDCV-QTMHVTGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,2aR,6R,8aS,8bR)-6-Phenyl-2-trimethylsilanylmethyl-octahydro-1,8-dioxa-5a-aza-acenaphthylene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到(4R,9S,9aS)-4-phenyl-9-vinyloctahydropyrido[2,1-c][1,4]oxazin-1-ol
  参考文献：
  名称：

  The tetrahydrooxazinone way to enantiopure α-amino acids: Synthesis of cis and trans 3-vinyl pipecolic acids via an intramolecular reaction between an iminium ion and an allylsilane moieties

  摘要：

  Reaction of glyoxal with a derivative of (R)-phenylglycinol having an allylsilane side-chain afforded a transient iminium ion. Intramolecular reaction of the iminium ion and the allylsilane moieties occurred in a totally stereoselective way. Straightforward transformations ultimately led to enantiopure either cis or trans 3-vinyl pipecolic acid methyl ester. The stereochemical course of this reaction was rationalized via AMI calculations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00486-4
• 作为产物：
  描述：

  D-苯甘氨醇 在 二异丙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 362.0h， 生成 (2S,2aR,6R,8aS,8bR)-6-Phenyl-2-trimethylsilanylmethyl-octahydro-1,8-dioxa-5a-aza-acenaphthylene
  参考文献：
  名称：

  The tetrahydrooxazinone way to enantiopure α-amino acids: Synthesis of cis and trans 3-vinyl pipecolic acids via an intramolecular reaction between an iminium ion and an allylsilane moieties

  摘要：

  Reaction of glyoxal with a derivative of (R)-phenylglycinol having an allylsilane side-chain afforded a transient iminium ion. Intramolecular reaction of the iminium ion and the allylsilane moieties occurred in a totally stereoselective way. Straightforward transformations ultimately led to enantiopure either cis or trans 3-vinyl pipecolic acid methyl ester. The stereochemical course of this reaction was rationalized via AMI calculations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00486-4