2S,5S,6R-2-carbethoxymethyl-4,5-dimethyl-6-phenyl-morpholin-3-one | 497157-61-6

• 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: 2S,5S,6R-2-carbethoxymethyl-4,5-dimethyl-6-phenyl-morpholin-3-one
• 英文别名: ethyl 2-[(2S,5S,6R)-4,5-dimethyl-3-oxo-6-phenylmorpholin-2-yl]acetate
• CAS: 497157-61-6
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: YEEGSKYXWVUSMQ-WHOFXGATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2S,5S,6R-2-carbethoxymethyl-4,5-dimethyl-6-phenyl-morpholin-3-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以96%的产率得到2-Morpholineacetic acid, 4,5-dimethyl-3-oxo-6-phenyl-, (2S,5S,6R)-
  参考文献：
  名称：

  Enantioselective synthesis of α-hydroxy γ-butyrolactones from an ephedrine-derived morpholine-dione

  摘要：

  An ephedrine-derived morpholine dione is employed in the enantioselective synthesis of (S)-alpha-hydroxy- gamma,gamma-dimethyl-gamma-butyrolactone and (S)-alpha-hydroxy gamma-butyrolactone. A one-pot alkylation/allylation protocol for the stereoselective conversion of the dione to 2-alkyl-2-allyl morpholinones, key intermediates for alpha-alkyl-alpha-hydroxy-gamma-butyrolactones, is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01151-1
• 作为产物：
  描述：

  盐酸麻黄碱 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 61.0h， 生成 2S,5S,6R-2-carbethoxymethyl-4,5-dimethyl-6-phenyl-morpholin-3-one
  参考文献：
  名称：

  Enantioselective synthesis of α-hydroxy γ-butyrolactones from an ephedrine-derived morpholine-dione

  摘要：

  An ephedrine-derived morpholine dione is employed in the enantioselective synthesis of (S)-alpha-hydroxy- gamma,gamma-dimethyl-gamma-butyrolactone and (S)-alpha-hydroxy gamma-butyrolactone. A one-pot alkylation/allylation protocol for the stereoselective conversion of the dione to 2-alkyl-2-allyl morpholinones, key intermediates for alpha-alkyl-alpha-hydroxy-gamma-butyrolactones, is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01151-1

文献信息

• The synthesis of (S)-(+)-pantolactone and its analogues from an ephedrine-derived morpholinone
  作者：Bidhan A. Shinkre、Abdul Rakeeb A.S. Deshmukh

  DOI：10.1016/j.tetasy.2004.02.022

  日期：2004.4

  An efficient general route for the enantioselective synthesis of (S)-(+)-pantolactone and its analogues has been developed from an ephedrine-derived chiral morpholin-3-one. Selective dialkylation of an ephedrine-derived chiral template without epimerization is the key step in this synthesis. (C) 2004 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of α-hydroxy γ-butyrolactones from an ephedrine-derived morpholine-dione
  作者：Sunil V Pansare、Bidhan A Shinkre、Annyt Bhattacharyya

  DOI：10.1016/s0040-4020(02)01151-1

  日期：2002.10

  An ephedrine-derived morpholine dione is employed in the enantioselective synthesis of (S)-alpha-hydroxy- gamma,gamma-dimethyl-gamma-butyrolactone and (S)-alpha-hydroxy gamma-butyrolactone. A one-pot alkylation/allylation protocol for the stereoselective conversion of the dione to 2-alkyl-2-allyl morpholinones, key intermediates for alpha-alkyl-alpha-hydroxy-gamma-butyrolactones, is described. (C) 2002 Elsevier Science Ltd. All rights reserved.