(3R,6S,1'S)-4-(1'-phenylethyl)-3-(2-propen-1-yl)-6-methyl-1,4-morpholin-2,5-dione | 176966-48-6

• 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: (3R,6S,1'S)-4-(1'-phenylethyl)-3-(2-propen-1-yl)-6-methyl-1,4-morpholin-2,5-dione
• 英文别名: (3R,6S)-6-methyl-4-[(1S)-1-phenylethyl]-3-prop-2-enylmorpholine-2,5-dione
• CAS: 176966-48-6
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: BSTJZWNWZRHORG-SGMGOOAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 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：

  (3R,6S,1'S)-4-(1'-phenylethyl)-3-(2-propen-1-yl)-6-methyl-1,4-morpholin-2,5-dione 在 氨 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 120.0h， 生成 (3R,5R)-5-(hydroxymethyl)-3-[(S)-(1-phenylethyl)amino]tetrahydrofuran-2-one
  参考文献：
  名称：

  Chiral 1,4-morpholin-2,5-dione derivatives as α-glucosidase inhibitors: Part 2

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2005.03.007
• 作为产物：
  描述：

  丙烯酰碘 、 (6S,1'S)-6-methyl-4-(1'-phenylethyl)-1,4-morpholine-2,5-dione 在 lithium hexamethyldisilazane 作用下， 生成 (3R,6S,1'S)-4-(1'-phenylethyl)-3-(2-propen-1-yl)-6-methyl-1,4-morpholin-2,5-dione
  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