(6S,1'S)-6-methyl-4-(1'-phenylethyl)-1,4-morpholine-2,5-dione | 174591-35-6

• 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: (6S,1'S)-6-methyl-4-(1'-phenylethyl)-1,4-morpholine-2,5-dione
• 英文别名: (6S)-4-N-((S)-1-phenethyl)-6-methyl-1,4-morpholin-2,5-dione；(6S)-6-methyl-4-[(1S)-1-phenylethyl]morpholine-2,5-dione
• CAS: 174591-35-6
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: CPLRCYRMTVRFAP-UWVGGRQHSA-N

物化性质

• 沸点：
  457.1±45.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (6S,1'S)-6-methyl-4-(1'-phenylethyl)-1,4-morpholine-2,5-dione 在 氨 、 碘 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 (3R,5S)-5-((R)-2-Benzyloxy-1-iodo-ethyl)-3-((S)-1-phenyl-ethylamino)-dihydro-furan-2-one
  参考文献：
  名称：

  Stereoselective synthesis of unnatural aminoacids cis-4-hydroxyproline and bulgecinine

  摘要：

  A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively, The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2), (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00079-1
• 作为产物：
  描述：

  (4S)-N-((S)-1-phenethyl)-4-phenyl-3-((2S,R)-2-chloropropionyl)-3-aza-ethylpentanoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (6S,1'S)-6-methyl-4-(1'-phenylethyl)-1,4-morpholine-2,5-dione 、 (6R)-4-N-((S)-1-phenethyl)-6-methyl-1,4-morpholin-2,5-dione
  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

文献信息

• Chiral 1,4-Morpholine-2,5-diones. Synthesis and Evaluation as Glucosidase Inhibitors
  作者：Antonio Arcelli、Daniele Balducci、Alessandro Grandi、Gianni Porzi、Monica Sandri、Sergio Sandri

  DOI：10.1007/s00706-004-0195-5

  日期：2004.8

  A series of chiral 1,4-morpholine-2,5-dione derivatives were synthesized. These substrates behave as non competitive inhibitors against α-glucosidase showing a moderate inhibition ( Ki < 0.8 m M ) and were found inactive towards β-glucosidase.

  合成了一系列手性的1,4-吗啉-2,5-二酮衍生物。这些底物表现为对α-葡萄糖苷酶的非竞争性抑制剂，表现出中等抑制作用（ Ki <0.8 m M ），被发现对β-葡萄糖苷酶无活性。
• Synthesis of new chiral 1,4-morpholin-2,5-dione derivatives and evaluation as α-glucosidase inhibitors. Part 3
  作者：Antonio Arcelli、Daniele Balducci、Sonia de Fatima Estevao Neto、Gianni Porzi、Monica Sandri

  DOI：10.1016/j.tetasy.2007.02.013

  日期：2007.3

  A series of chiral 1,4-morpholin-2,5-dione derivatives were synthesized starting from chiral synthons 1 and 2, monolactim ethers derived from L- valine, and the absolute configurations of the new stereocentres were assigned. The substrates investigated behave as noncompetitive inhibitors against alpha-glucosidases and Eire inactive towards beta-glucosidase, alpha-mannosidase and alpha-galactosidase. Three of these substrates show very good and specific inhibition abilities towards alpha-glucosidase. (c) 2007 Elsevier Ltd. All rights reserved.
• Chiral 1,4-morpholin-2,5-dione derivatives as α-glucosidase inhibitors: Part 2
  作者：Antonio Arcelli、Daniele Balducci、Alessandro Grandi、Gianni Porzi、Monica Sandri、Sergio Sandri

  DOI：10.1016/j.tetasy.2005.03.007

  日期：2005.4

  A series of chiral 1,4-morpholin-2,5-dione derivatives were synthesized starting from chiral synthons 1 and 2, diastereomeric monolactim ethers derived from L-valine. The Compounds investigated, were inactive toward beta-glucosidase, alpha-mannosidase and alpha-galactosidase but behave as noncompetitive inhibitors against the alpha-glucosidase (from Saccharomices cervisiae) with some showing a good inhibition ability (0.05 < Ki < 0. 18 mM). (c) 2005 Elsevier Ltd. All rights reserved.
• 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 unnatural aminoacids cis-4-hydroxyproline and bulgecinine
  作者：Alessandra Madau、Gianni Porzi、Sergio Sandri

  DOI：10.1016/0957-4166(96)00079-1

  日期：1996.3

  A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively, The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2), (C) 1996 Elsevier Science Ltd