4-(2-hydroxy-(1R)-phenylethyl)thiomorpholin-3-one | 627064-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 4-(2-hydroxy-(1R)-phenylethyl)thiomorpholin-3-one
• 英文别名: 4-[(1R)-2-hydroxy-1-phenylethyl]thiomorpholin-3-one
• CAS: 627064-71-5
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: LPYZZUTWAYMLMX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 4-(2-hydroxy-(1R)-phenylethyl)thiomorpholin-3-one 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以96%的产率得到(2R)-benzyl-4-[2'-hydroxy-(1'R)-phenylethyl]thiomorpholin-3-one
  参考文献：
  名称：

  Efficient enantioselective synthesis of 2-substituted thiomorpholin-3-ones

  摘要：

  The synthesis of enantiomerically pure 4-(2-hydroxy-(1R)-phenylethyl)-thiomorpholin-3-one 2 from (R)-phenylglycine methyl ester, S-benzylthioglycolic acid and bromoacetic acid is reported. Stereoselective C-2 alkylation of 2, performed using various electrophiles, leads to enantiomerically pure 2-substituted thiomorpholin-3-ones after N-deprotection. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.010
• 作为产物：
  描述：

  4-[(1R)-[2-(tert-butyldimethylsilanyloxy)]phenylethyl]thiomorpholin-3-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到4-(2-hydroxy-(1R)-phenylethyl)thiomorpholin-3-one
  参考文献：
  名称：

  Efficient enantioselective synthesis of 2-substituted thiomorpholin-3-ones

  摘要：

  The synthesis of enantiomerically pure 4-(2-hydroxy-(1R)-phenylethyl)-thiomorpholin-3-one 2 from (R)-phenylglycine methyl ester, S-benzylthioglycolic acid and bromoacetic acid is reported. Stereoselective C-2 alkylation of 2, performed using various electrophiles, leads to enantiomerically pure 2-substituted thiomorpholin-3-ones after N-deprotection. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.010

文献信息

• Efficient enantioselective synthesis of 2-substituted thiomorpholin-3-ones
  作者：Nicolas Franceschini、Sophie Da Nascimento、Pascal Sonnet、Dominique Guillaume

  DOI：10.1016/j.tetasy.2003.09.010

  日期：2003.10

  The synthesis of enantiomerically pure 4-(2-hydroxy-(1R)-phenylethyl)-thiomorpholin-3-one 2 from (R)-phenylglycine methyl ester, S-benzylthioglycolic acid and bromoacetic acid is reported. Stereoselective C-2 alkylation of 2, performed using various electrophiles, leads to enantiomerically pure 2-substituted thiomorpholin-3-ones after N-deprotection. (C) 2003 Elsevier Ltd. All rights reserved.