(2R,3R)-2,3-Bis-methoxymethyl-1,4-dioxa-spiro[4.5]decane | 136413-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-2,3-Bis-methoxymethyl-1,4-dioxa-spiro[4.5]decane
• 英文别名: (2R,3R)-2,3-bis(methoxymethyl)-1,4-dioxaspiro[4.5]decane
• CAS: 136413-66-6
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: UWZUMOUTSJSRGR-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-Bis-methoxymethyl-1,4-dioxa-spiro[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 26.0h， 生成 (2S)-2-(ethoxycarbonylamino)cyclohexanone (1R,2R)-1,2-bis(methoxymethyl)ethylene acetal
  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
• 作为产物：
  描述：

  (R,R)-(+)-1,4-二甲氧基-2,3-丁二醇 、 环己酮 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 以62%的产率得到(2R,3R)-2,3-Bis-methoxymethyl-1,4-dioxa-spiro[4.5]decane
  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

• Optically Pure 3,6-Dioxazocan-2-one Derivatives by Intramolecular Cycloaddition of Azidoformates and their Opening to Substituted α-Amino Ketones
  作者：Marco de Santis、Stefania Fioravanti、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1002/(sici)1099-0690(199911)1999:11<2709::aid-ejoc2709>3.0.co;2-h

  日期：1999.11

  Azidoformates derived from chiral enol ethers, when irradiated, give 3,6-dioxazocan-2-one derivatives 7 by a highly diastereoselective intramolecular cycloaddition. The hydrolysis of 7 gives a single derivative of 2-aminocyclohexanone.

  衍生自手性烯醇醚的叠氮基甲酸酯，经辐射后，会通过高度非对映选择性的分子内环加成反应生成3,6-dioxazocan-2-one衍生物7。7的水解产生2-氨基环己酮的单一衍生物。