(5R,6S)-5-methyl-6-phenylmorpholin-3-one | 180683-53-8

• 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: (5R,6S)-5-methyl-6-phenylmorpholin-3-one
• 英文别名: 5-methyl-6-phenyl-morpholin-3-one；cis-5-Methyl-6-phenyl-3-morpholinon
• CAS: 180683-53-8
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: UJEPHPADGSWWRM-LDYMZIIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯甲基甲基醚 、 (5R,6S)-5-methyl-6-phenylmorpholin-3-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 以82%的产率得到(5R,6S)-4-(methoxymethyl)-5-methyl-6-phenylmorpholin-3-one
  参考文献：
  名称：

  Alkylation Studies of N-Protected-5-substituted Morpholin-3-ones. A Stereoselective Approach to Novel Methylene Ether Dipeptide Isosteres

  摘要：

  We have developed a versatile new synthesis of the Psi[CH2O] pseudopeptides from N-protected-5-substituted morpholin-3-ones. The morpholin-3-ones are prepared in two steps from the corresponding amino alcohols by treatment with ethyl chloroacetate, followed by protection of the amide, We found that direct alkylation of the protected morpholin-3-ones gives the expected alkylation product where the electrophile approaches from the face opposite to the existing side chain (derived from the amino alcohol). If an S amino alcohol is used, this procedure results in the formation of the (SE) Psi[CH2O] dipeptide. Alternatively, the (S,S) Psi[CH2O] dipeptide can be obtained if the protected morpholin-3-one enolate is quenched with an aldehyde and the aldol product is dehydrated and reduced. We have explored an alkylation/deprotonation/kinetic protonation scheme which is also amenable to the preparation of (S,S) pseudodipetides. It is, of course, possible to obtain the corresponding (R,R) and (S,R) Psi[CH2O] dipeptides by simply selecting the appropriate amino alcohols and reaction conditions. Finally, we have established that this method is general and can be applied to the preparation of numerous Psi[CH2O] dipeptides which were previously unavailable by existing methods.

  DOI：

  10.1021/jo960496w
• 作为产物：
  描述：

  左旋去甲麻黄碱 、 氯乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 以78%的产率得到(5R,6S)-5-methyl-6-phenylmorpholin-3-one
  参考文献：
  名称：

  Alkylation Studies of N-Protected-5-substituted Morpholin-3-ones. A Stereoselective Approach to Novel Methylene Ether Dipeptide Isosteres

  摘要：

  We have developed a versatile new synthesis of the Psi[CH2O] pseudopeptides from N-protected-5-substituted morpholin-3-ones. The morpholin-3-ones are prepared in two steps from the corresponding amino alcohols by treatment with ethyl chloroacetate, followed by protection of the amide, We found that direct alkylation of the protected morpholin-3-ones gives the expected alkylation product where the electrophile approaches from the face opposite to the existing side chain (derived from the amino alcohol). If an S amino alcohol is used, this procedure results in the formation of the (SE) Psi[CH2O] dipeptide. Alternatively, the (S,S) Psi[CH2O] dipeptide can be obtained if the protected morpholin-3-one enolate is quenched with an aldehyde and the aldol product is dehydrated and reduced. We have explored an alkylation/deprotonation/kinetic protonation scheme which is also amenable to the preparation of (S,S) pseudodipetides. It is, of course, possible to obtain the corresponding (R,R) and (S,R) Psi[CH2O] dipeptides by simply selecting the appropriate amino alcohols and reaction conditions. Finally, we have established that this method is general and can be applied to the preparation of numerous Psi[CH2O] dipeptides which were previously unavailable by existing methods.

  DOI：

  10.1021/jo960496w

文献信息

• Alkylation Studies of <i>N</i>-Protected-5-substituted Morpholin-3-ones. A Stereoselective Approach to Novel Methylene Ether Dipeptide Isosteres
  作者：Bryan H. Norman、Julian S. Kroin

  DOI：10.1021/jo960496w

  日期：1996.1.1

  We have developed a versatile new synthesis of the Psi[CH2O] pseudopeptides from N-protected-5-substituted morpholin-3-ones. The morpholin-3-ones are prepared in two steps from the corresponding amino alcohols by treatment with ethyl chloroacetate, followed by protection of the amide, We found that direct alkylation of the protected morpholin-3-ones gives the expected alkylation product where the electrophile approaches from the face opposite to the existing side chain (derived from the amino alcohol). If an S amino alcohol is used, this procedure results in the formation of the (SE) Psi[CH2O] dipeptide. Alternatively, the (S,S) Psi[CH2O] dipeptide can be obtained if the protected morpholin-3-one enolate is quenched with an aldehyde and the aldol product is dehydrated and reduced. We have explored an alkylation/deprotonation/kinetic protonation scheme which is also amenable to the preparation of (S,S) pseudodipetides. It is, of course, possible to obtain the corresponding (R,R) and (S,R) Psi[CH2O] dipeptides by simply selecting the appropriate amino alcohols and reaction conditions. Finally, we have established that this method is general and can be applied to the preparation of numerous Psi[CH2O] dipeptides which were previously unavailable by existing methods.