(3R,6S,1'S)-3,6-dimethyl-4-N-(1'-phenethyl)-1,4-morpholin-2,5-dione | 174591-36-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,6S,1'S)-3,6-dimethyl-4-N-(1'-phenethyl)-1,4-morpholin-2,5-dione
• 英文别名: (3R,6S)-4-N-((S)-1-phenethyl)-3,6-dimethyl-1,4-morpholin-2,5-dione；(3R,6S)-3,6-dimethyl-4-[(1S)-1-phenylethyl]morpholine-2,5-dione
• CAS: 174591-36-7
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: ZXGOHZIBKZJCEQ-AXFHLTTASA-N

物化性质

• 沸点：
  455.2±45.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,6S,1'S)-3,6-dimethyl-4-N-(1'-phenethyl)-1,4-morpholin-2,5-dione 在 氢碘酸 作用下， 反应 1.0h， 以100%的产率得到D-丙氨酸
  参考文献：
  名称：

  Enantioselective synthesis of (R)-and (S)-α-aminoacids using (6S)- and (6R)-6-methyl-morpholine-2,5-dione derivatives

  摘要：

  The alkylation of both 3 and 4 gives exclusively the trans derivatives 5 and 6, respectively, with >98% diastereoselectivity. Cleavage of the morpholine-2,5-dione ring of 5 and 6 leads to enantiomerically pure (S)- and (R)-alpha-aminoacids, respectively. The configurations of stereogenic centers introduced on 3, 4, 5 and 6 have been assigned on the basis of the H-1-NMR data, conformational analysis and nOe measurements.

  DOI：

  10.1016/0957-4166(95)00435-1
• 作为产物：
  描述：

  (R)-2-[((S)-2-Acetoxy-propionyl)-((S)-1-phenyl-ethyl)-amino]-propionic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到(3R,6S,1'S)-3,6-dimethyl-4-N-(1'-phenethyl)-1,4-morpholin-2,5-dione
  参考文献：
  名称：

  Stereoselective synthesis of uncommon α,α′-dialkyl-α-aminoacids. Part 1

  摘要：

  The alkylation of the diastereomeric mixture of chiral morpholinone derivatives 4 and 5 occurs with good yield and trans induction. Cleavage of the alkylated products 6a,b,c,e gives enantiomerically pure uncommon land sterically constrained) alpha,alpha '-dialkyl-alpha-aminoacids. The absolute configuration of the new stereocentres of 4, 5, 6 and 7 has been assigned on the basis of the H-1-NMR spectra and NOE measurements. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00272-9

文献信息

• Enantioselective synthesis of (R)-and (S)-α-aminoacids using (6S)- and (6R)-6-methyl-morpholine-2,5-dione derivatives
  作者：Gianni Porzi、Sergio Sandri

  DOI：10.1016/0957-4166(95)00435-1

  日期：1996.1

  The alkylation of both 3 and 4 gives exclusively the trans derivatives 5 and 6, respectively, with >98% diastereoselectivity. Cleavage of the morpholine-2,5-dione ring of 5 and 6 leads to enantiomerically pure (S)- and (R)-alpha-aminoacids, respectively. The configurations of stereogenic centers introduced on 3, 4, 5 and 6 have been assigned on the basis of the H-1-NMR data, conformational analysis and nOe measurements.
• Stereoselective synthesis of uncommon α,α′-dialkyl-α-aminoacids. Part 1
  作者：Armando Carloni、Gianni Porzi、Sergio Sandri

  DOI：10.1016/s0957-4166(98)00272-9

  日期：1998.9

  The alkylation of the diastereomeric mixture of chiral morpholinone derivatives 4 and 5 occurs with good yield and trans induction. Cleavage of the alkylated products 6a,b,c,e gives enantiomerically pure uncommon land sterically constrained) alpha,alpha '-dialkyl-alpha-aminoacids. The absolute configuration of the new stereocentres of 4, 5, 6 and 7 has been assigned on the basis of the H-1-NMR spectra and NOE measurements. (C) 1998 Elsevier Science Ltd. All rights reserved.