ethyl N-[(2R,3R,7R)-2,3-dimethyl-1,4-dioxaspiro[4.5]decan-7-yl]carbamate | 189504-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl N-[(2R,3R,7R)-2,3-dimethyl-1,4-dioxaspiro[4.5]decan-7-yl]carbamate
• CAS: 189504-05-0
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: SUFZYYODPWFBDU-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-[(2R,3R,7R)-2,3-dimethyl-1,4-dioxaspiro[4.5]decan-7-yl]carbamate 在 potassium permanganate 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 24.5h， 生成 (2R)-2-(ethoxycarbonylamino)hexanedioic acid 、
  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：

  (2R,3R)-2,3-dimethyl-1,4-dioxaspiro[4.5]dec-7-ene 在 L-Selectride 、 calcium oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 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

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.