(3R,6S)-6-isopropyl-3-(2-propenyl)morpholine-2,5-dione | 205880-35-9

• 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)-6-isopropyl-3-(2-propenyl)morpholine-2,5-dione
• 英文别名: (3R,6S)-6-propan-2-yl-3-prop-2-enylmorpholine-2,5-dione
• CAS: 205880-35-9
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: OKANGZACIMLMRB-SFYZADRCSA-N

物化性质

• 沸点：
  407.3±38.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,6S)-6-isopropyl-3-(2-propenyl)morpholine-2,5-dione 在 盐酸 作用下， 以71%的产率得到D-烯丙基甘氨酸
  参考文献：
  名称：

  Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions

  摘要：

  已经应用了三种不同的电化学方法来合成用于二分立体选择性氨基烷基化反应的手性构建块。这些方法包括：A. 酰胺和碳酸酯的直接阳极α-甲氧基化；B. α-氨基酸衍生物的阳极甲氧基化脱羧（Hofer-Moest反应）C. 间接NaCl介导的α-氨基酸衍生物的阳极α-甲氧基化。描述了这些构建块在合成手性纯α-氨基酸、二分手性1,2-氨基醇和手性1,3-二胺中的应用。

  DOI：

  10.1051/jcp/1996930575
• 作为产物：
  描述：

  (3RS,6S)-6-isopropyl-3-methoxymorpholine-2,5-dione 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到(3R,6S)-6-isopropyl-3-(2-propenyl)morpholine-2,5-dione
  参考文献：
  名称：

  Electrogenerated chiral cationic glycine equivalents — Part 2: Chiral 3-methoxy-2,5-morpholinediones from (S)-α-hydroxy acids and dimethyl aminomalonate

  摘要：

  Chiral 3-methoxy-2,5-morpholinediones which are cyclic N,O-acetals have proved to be excellent chiral cationic amino acid equivalents, especially if larger nucleophiles are employed. They are easily obtained from dipeptolides formed between chiral alpha-hydroxy acids and dimethyl amino malonate via regioselective electrochemical methoxylation followed by intramolecular lactonization after decarboxylation. The lactonization can be performed quantitatively from the open-chain peptolide by condenzation under reduced pressure at elevated temperature. The easy separation of the desired amino acid and the alpha-hydroxy acid being the chiral auxiliary by extraction is valuable. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00082-9

文献信息

• Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions
  作者：P Brungs、K Danielmeier、J Jakobi、C Nothhelfer、A Stahl、A Zietlow、E Steckhan

  DOI：10.1051/jcp/1996930575

  日期：——

  Three different electrochemical methods have been applied for the synthesis of chiral building blocks for diastereoselective amidoalkylation reactions. These are A. the direct anodic α-methoxylation of amides and carbamates; B. anodic methoxylative decarboxylation of α-amino acid derivatives (Hofer-Moest reaction) C. indirect NaCl mediated anodic α-methoxylation of α-amino acid derivatives. The application of these building blocks for the synthesis of enantiomerically pure α-amino acids, dichiral 1,2-amino alcohols and chiral 1,3-diamines is described.

  已经应用了三种不同的电化学方法来合成用于二分立体选择性氨基烷基化反应的手性构建块。这些方法包括：A. 酰胺和碳酸酯的直接阳极α-甲氧基化；B. α-氨基酸衍生物的阳极甲氧基化脱羧（Hofer-Moest反应）C. 间接NaCl介导的α-氨基酸衍生物的阳极α-甲氧基化。描述了这些构建块在合成手性纯α-氨基酸、二分手性1,2-氨基醇和手性1,3-二胺中的应用。
• Electrogenerated chiral cationic glycine equivalents — Part 2: Chiral 3-methoxy-2,5-morpholinediones from (S)-α-hydroxy acids and dimethyl aminomalonate
  作者：Georgios Kardassis、Peter Brungs、Christoph Nothhelfer、Eberhard Steckhan

  DOI：10.1016/s0040-4020(98)00082-9

  日期：1998.4

  Chiral 3-methoxy-2,5-morpholinediones which are cyclic N,O-acetals have proved to be excellent chiral cationic amino acid equivalents, especially if larger nucleophiles are employed. They are easily obtained from dipeptolides formed between chiral alpha-hydroxy acids and dimethyl amino malonate via regioselective electrochemical methoxylation followed by intramolecular lactonization after decarboxylation. The lactonization can be performed quantitatively from the open-chain peptolide by condenzation under reduced pressure at elevated temperature. The easy separation of the desired amino acid and the alpha-hydroxy acid being the chiral auxiliary by extraction is valuable. (C) 1998 Elsevier Science Ltd. All rights reserved.