ethyl (Z)-2-((5S,6R)-4,5-dimethyl-3-oxo-6-phenylmorpholin-2-ylidene)acetate | 497157-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (Z)-2-((5S,6R)-4,5-dimethyl-3-oxo-6-phenylmorpholin-2-ylidene)acetate
• 英文别名: (Z)-5S,6R-2-carbethoxymethylidene-4,5-dimethyl-6-phenyl-morpholin-3-one；ethyl (2Z)-2-[(5S,6R)-4,5-dimethyl-3-oxo-6-phenylmorpholin-2-ylidene]acetate
• CAS: 497157-60-5
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: DNOFKXSHMUVHMO-XKXUVZMISA-N

物化性质

• 沸点：
  463.1±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-2-((5S,6R)-4,5-dimethyl-3-oxo-6-phenylmorpholin-2-ylidene)acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以100%的产率得到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
• 作为产物：
  描述：

  盐酸麻黄碱 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 49.0h， 生成 ethyl (Z)-2-((5S,6R)-4,5-dimethyl-3-oxo-6-phenylmorpholin-2-ylidene)acetate
  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

• A General Approach to 1-Hydroxymethylquinolizidine and 8-Hydroxymethylindolizidine Stereoisomers: Synthesis of (+)-Epitashiromine and Formal Syntheses of (+)-Epilupinine and (+)-Tashiromine
  作者：Rakesh G. Thorat、Sunil V. Pansare

  DOI：10.1002/ejoc.201301078

  日期：2013.11

  A general strategy for the synthesis of structurally and stereochemically related indolizidine and quinolizidine alkaloids was developed. The methodology involves regio- and stereoselective 1,3-dipolar cycloadditions of simple nitrones with ephedrine-derived alkylidenemorpholinones. The intermediate isoxazolidines can be converted into either the indolizidine or the quinolizidine motif depending on

  开发了合成结构和立体化学相关的吲哚里西啶和喹尼西啶生物碱的一般策略。该方法涉及简单硝酮与麻黄碱衍生的亚烷基吗啉酮的区域和立体选择性 1,3-偶极环加成反应。中间体异恶唑烷可以转化为吲哚里西啶或喹唑啉基序，这取决于硝酮和亲偶极体上的取代基。该方法应用于 (+)-epitashiromine 的合成以及 (+)-epilupinine 和 (+)-tashiromine 的正式合成。