ethyl (1'S,4R,5R,6'R)-4,5-dimethylspiro[1,3-dioxolane-2,3'-7-azabicyclo[4.1.0]heptane]-7'-carboxylate | 189503-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: ethyl (1'S,4R,5R,6'R)-4,5-dimethylspiro[1,3-dioxolane-2,3'-7-azabicyclo[4.1.0]heptane]-7'-carboxylate
• CAS: 189503-90-0
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: NVGPTGGSRFBFCI-WCIIABOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1'S,4R,5R,6'R)-4,5-dimethylspiro[1,3-dioxolane-2,3'-7-azabicyclo[4.1.0]heptane]-7'-carboxylate 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以69%的产率得到ethyl N-[(2R,3R,7R)-2,3-dimethyl-1,4-dioxaspiro[4.5]decan-7-yl]carbamate
  参考文献：
  名称：

  Stereoselectivity in the amination of chiral cyclohex-3-en-1-one ketals

  摘要：

  Optically active cyclohex-3-en-1-one ketals by photolysis of N(3)CO(2)Et or N3C(OEt)NMs or by CaO induced alpha-elimination of NsONHCO(2)Et give diastereomeric aziridines (up to 72% yields, up to 60% d.e.). A simple HPLC separation allows to obtain practically pure aziridines. The conversion of the main product to the ketal of (R)-N-(ethoxycarbonyl)-beta-aminocyclohexanone is also reported and a further oxidation directly gives a derivative of(R)-2-aminoadipic acid. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00161-0
• 作为产物：
  描述：

  2-环己烯-1-酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 、 calcium oxide 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 ethyl (1'S,4R,5R,6'R)-4,5-dimethylspiro[1,3-dioxolane-2,3'-7-azabicyclo[4.1.0]heptane]-7'-carboxylate
  参考文献：
  名称：

  Stereoselectivity in the amination of chiral cyclohex-3-en-1-one ketals

  摘要：

  Optically active cyclohex-3-en-1-one ketals by photolysis of N(3)CO(2)Et or N3C(OEt)NMs or by CaO induced alpha-elimination of NsONHCO(2)Et give diastereomeric aziridines (up to 72% yields, up to 60% d.e.). A simple HPLC separation allows to obtain practically pure aziridines. The conversion of the main product to the ketal of (R)-N-(ethoxycarbonyl)-beta-aminocyclohexanone is also reported and a further oxidation directly gives a derivative of(R)-2-aminoadipic acid. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00161-0

文献信息

• Stereoselectivity in the amination of chiral cyclohex-3-en-1-one ketals
  作者：Stefania Fioravanti、Giuseppe Luna、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1016/s0040-4020(97)00161-0

  日期：1997.3

  Optically active cyclohex-3-en-1-one ketals by photolysis of N(3)CO(2)Et or N3C(OEt)NMs or by CaO induced alpha-elimination of NsONHCO(2)Et give diastereomeric aziridines (up to 72% yields, up to 60% d.e.). A simple HPLC separation allows to obtain practically pure aziridines. The conversion of the main product to the ketal of (R)-N-(ethoxycarbonyl)-beta-aminocyclohexanone is also reported and a further oxidation directly gives a derivative of(R)-2-aminoadipic acid. (C) 1997 Elsevier Science Ltd.