((2R,3R,6S)-2,3-Dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-carbamic acid ethyl ester | 113667-33-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3R,6S)-2,3-Dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-carbamic acid ethyl ester
• 英文别名: ethyl N-[(2R,3R,6S)-2,3-dimethyl-1,4-dioxaspiro[4.5]decan-6-yl]carbamate
• CAS: 113667-33-7
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: MCTVWSZRJHUDQO-MXWKQRLJSA-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

• 作为产物：
  描述：

  trans-2,3-dimethyl-1,4-dioxaspiro[4,5]decane 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 ((2R,3R,6S)-2,3-Dimethyl-1,4-dioxa-spiro[4.5]dec-6-yl)-carbamic acid ethyl ester
  参考文献：
  名称：

  Asymmetric formation of CN bonds in chiral enol ethers

  摘要：

  Attack of EtO2CN on an enol ether carrying (S,S)-hydrobenzoin as chiral auxiliary gives diastereoselective aziridination with diastereomeric excess > 95%. Easy subsequent hydrolysis gives partially racemised alpha-amino ketone 4. Other chiral auxiliaries does not allow isolation of intermediate aziridines and the alpha-amino ketone is isolated with a 75:25 enantiomeric ratio. The thermolysis of EtO2CN3 in most of the same enol ethers gives the acetals of the alpha-amino ketone with prevailing opposite configuration at the new formed chiral centre.

  DOI：

  10.1016/s0040-4020(01)86538-8

文献信息

• FIORAVANTI, STEFANIA;LORETO, M. ANTONIETTA;PELLACANI, LUCIO;TARDELLA, PAO+, J. CHEM. RES. SYNOP.,(1987) N 9, 310-311
  作者：FIORAVANTI, STEFANIA、LORETO, M. ANTONIETTA、PELLACANI, LUCIO、TARDELLA, PAO+

  DOI：——

  日期：——
• Asymmetric formation of CN bonds in chiral enol ethers
  作者：Stefania Fioravanti、M.Antonietta Loreto、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1016/s0040-4020(01)86538-8

  日期：1991.7

  Attack of EtO2CN on an enol ether carrying (S,S)-hydrobenzoin as chiral auxiliary gives diastereoselective aziridination with diastereomeric excess > 95%. Easy subsequent hydrolysis gives partially racemised alpha-amino ketone 4. Other chiral auxiliaries does not allow isolation of intermediate aziridines and the alpha-amino ketone is isolated with a 75:25 enantiomeric ratio. The thermolysis of EtO2CN3 in most of the same enol ethers gives the acetals of the alpha-amino ketone with prevailing opposite configuration at the new formed chiral centre.