methyl (3R,4S)-2-hydroxy-4-phenyl-3-propan-2-yl-3,4-dihydro-2H-pyran-6-carboxylate | 588689-89-8

• 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: methyl (3R,4S)-2-hydroxy-4-phenyl-3-propan-2-yl-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 588689-89-8
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: CVISZGPTMOSNDZ-OJDRRSAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3R,4S)-2-hydroxy-4-phenyl-3-propan-2-yl-3,4-dihydro-2H-pyran-6-carboxylate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以93%的产率得到
  参考文献：
  名称：

  模块化设计的有机催化剂催化的高对映选择性逆电子需求杂Diels-Alder反应

  摘要：

  MDO震撼！脯氨酸和（2 S，3a S，7a S）-八氢-1 H-吲哚-2-羧酸都是醛和缺电子的烯酮之间反电子需求的杂Diels-Alder反应的不良催化剂。但是，通过与金鸡纳生物碱衍生的硫脲的自组装形成模块化设计的有机催化剂（MDO）可以显着提高这些催化剂的效率（请参见方案； PCC =氯铬酸吡啶鎓）。

  DOI：

  10.1002/chem.201300168
• 作为产物：
  描述：

  methyl 4-phenyl-2-oxo-3-butenoate 、 异戊醛 在 N,N-dimethylbenzylamine prolinol trimethylsilyl ether 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以98%的产率得到
  参考文献：
  名称：

  A highly enantioselective [4+2] cycloaddition involving aldehydes and β,γ-unsaturated-α-keto esters

  摘要：

  A stereoselective inverse electron demand oxo-Diels-Alder reaction involving electron poor dienes (gamma-aryl-beta,gamma-unsaturated-alpha-keto ester) and electron rich dienophiles has been studied. These cycloaddition reactions are extremely useful for the construction of O-, N-, S-centered heterocyclic compounds, which are routinely used in both synthetic organic and medicinal chemistry. The [4+2] hetero cycloaddition reactions involving various aldehydes and beta,gamma-unsaturated-alpha-keto esters were carried out in which three different types of substituted proline catalysts were examined. For these reactions, high selectivities (enantiomeric excess 93-98%) were obtained using catalyst 3. Due to the bulkiness of catalyst 3, compared to the other catalysts tested, it is more efficient at catalyzing these type reactions. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.09.019

文献信息

• Highly Enantioselective Inverse-Electron-Demand Hetero-Diels-Alder Reactions Catalyzed by Modularly Designed Organocatalysts
  作者：Debarshi Sinha、Sandun Perera、John Cong-Gui Zhao

  DOI：10.1002/chem.201300168

  日期：2013.5.27

  rocks! Proline and (2S,3aS,7aS)‐octahydro‐1H‐indole‐2‐carboxylic acid are both poor catalysts for the inverse‐electron‐demand hetero‐Diels–Alder reactions between aldehydes and electron‐deficient enones. However, forming modularly designed organocatalysts (MDOs) through their self‐assembly with cinchona alkaloid‐derived thioureas can dramatically improve the efficiency of these catalysts (see scheme;

  MDO震撼！脯氨酸和（2 S，3a S，7a S）-八氢-1 H-吲哚-2-羧酸都是醛和缺电子的烯酮之间反电子需求的杂Diels-Alder反应的不良催化剂。但是，通过与金鸡纳生物碱衍生的硫脲的自组装形成模块化设计的有机催化剂（MDO）可以显着提高这些催化剂的效率（请参见方案； PCC =氯铬酸吡啶鎓）。
• A highly enantioselective [4+2] cycloaddition involving aldehydes and β,γ-unsaturated-α-keto esters
  作者：Nanda Kumar Katakam、Yejin Kim、Allan D. Headley

  DOI：10.1016/j.tetasy.2017.09.019

  日期：2017.11

  A stereoselective inverse electron demand oxo-Diels-Alder reaction involving electron poor dienes (gamma-aryl-beta,gamma-unsaturated-alpha-keto ester) and electron rich dienophiles has been studied. These cycloaddition reactions are extremely useful for the construction of O-, N-, S-centered heterocyclic compounds, which are routinely used in both synthetic organic and medicinal chemistry. The [4+2] hetero cycloaddition reactions involving various aldehydes and beta,gamma-unsaturated-alpha-keto esters were carried out in which three different types of substituted proline catalysts were examined. For these reactions, high selectivities (enantiomeric excess 93-98%) were obtained using catalyst 3. Due to the bulkiness of catalyst 3, compared to the other catalysts tested, it is more efficient at catalyzing these type reactions. (C) 2017 Elsevier Ltd. All rights reserved.