5S,6R-4,5-dimethyl-6-phenyl-morpholin-2,3-dione | 78927-93-2

• 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: 5S,6R-4,5-dimethyl-6-phenyl-morpholin-2,3-dione
• 英文别名: (5S,6R)-4,5-dimethyl-6-phenylmorpholine-2,3-dione
• CAS: 78927-93-2
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: APLZFAOVXIKLKF-WPRPVWTQSA-N

物化性质

• 熔点：
  182 °C
• 沸点：
  320.5±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  5S,6R-4,5-dimethyl-6-phenyl-morpholin-2,3-dione 在 硫酸 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.03h， 生成 2R,3S,6R-3,4-dimethyl-2-phenyl-1,14,16-trioxa-4-aza-dispiro[5.0.5.4]hexadecane-5-one
  参考文献：
  名称：

  Enantioselective synthesis of pantolactone analogues from an ephedrine-derived morpholine-dione

  摘要：

  An efficient enantioselective synthesis of beta,beta-dialkyl alpha-hydroxy gamma-butyrolactones, analogues of pantolactone, has been developed employing a stereoselective Prins reaction of chiral alkylidene morpholinones, as the key step. Enantioselective synthesis of a naturally occurring pantolactone homologue and a spiro analogue of pantolactone was achieved with this protocol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00408-3
• 作为产物：
  描述：

  盐酸麻黄碱 、 草酰氯单乙酯 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， 以85%的产率得到5S,6R-4,5-dimethyl-6-phenyl-morpholin-2,3-dione
  参考文献：
  名称：

  对-（-）-劳伦霉素的对映选择性方法。

  摘要：

  已经开发了一种收敛的对映选择性路线，该路线是用于合成海洋天然产物（+）-月桂酸的高级中间体的途径。该方法采用以手性仲醇为原料的基于麻黄碱的螺环氧化物的开环，半缩醛烯丙基化和闭环易位，这是在劳伦霉素中加工功能化的中环醚部分的关键步骤。

  DOI：

  10.1039/b803973a

文献信息

• Enantioselective Synthesis of Functionalized Quaternary Stereocenters
  作者：Amarender Manchoju、Rakesh G. Thorat、Sunil V. Pansare

  DOI：10.1002/ejoc.201500985

  日期：2015.9

  An enantioselective synthesis of functionalized quaternary stereocenters was developed from amino alcohol derived (bromoalkylidene)morpholinones. Stereoselective cross-coupling of the morpholinones with arylboronic acids or alkyl trifluoroborates provided a variety of disubstituted alkylidenemorpholinones. A highly stereoselective Prins reaction of the cross-coupling products generated the target quaternary

  从氨基醇衍生的（溴亚烷基）吗啉酮开发了功能化季立体中心的对映选择性合成。吗啉酮与芳基硼酸或三氟硼酸烷基酯的立体选择性交叉偶联提供了多种二取代的亚烷基吗啉酮。交叉偶联产物的高度立体选择性 Prins 反应生成了目标四元立体中心。Prins 产品很容易转化为各种具有四元立体中心的无环、对映体富集、功能化的构建块。
• Enantioselective synthesis of (R)-homocitric acid lactone
  作者：Sunil V. Pansare、Vikrant A. Adsool

  DOI：10.1016/j.tetlet.2007.08.005

  日期：2007.10

  An expedient enantioselective approach to (R)-homocitric acid lactone from an ephedrine-derived morpholine-dione, a cationic glycolate equivalent, is described.

  描述了从麻黄碱衍生的吗啉-二酮（阳离子乙醇酸酯等效物）对（R）-高酸内酯的简便对映选择性方法。
• 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。
• Enantioselective synthesis of β,β-dialkyl α-hydroxy γ-butyrolactones
  作者：Sunil V Pansare、Annyt Bhattacharyya

  DOI：10.1016/s0040-4039(01)01979-7

  日期：2001.12

  An ephedrine-derived morpholine dione is employed in the synthesis of chiral alkylidene morpholinones that are efficiently converted to beta -substituted alpha-gamma -dihydroxy butyramides, precursors of the corresponding butyrolactones. Enantioselective synthesis of a spiro analog of pantolactone as well as a naturally occurring pantolactone homolog is achieved with this protocol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enantioselective Synthesis of Functionalized Medium-Sized Oxacycles
  作者：Sunil V. Pansare、Vikrant A. Adsool

  DOI：10.1021/ol062484v

  日期：2006.12.1

  Enantioselective routes to functionalized, seven-, eight-, and nine-membered oxacycles that are amenable to further elaboration have been developed. Salient features of the methodology include highly diastereoselective and regioselective transformations of an ephedrine-derived epoxy morpholinone to functionalized precursors of the oxacycles. The ephedrine scaffold exerts remote stereocontrol in the functionalization of the appended oxacycle.