3-hydroxy-N-methoxy-3-(4-methoxyphenyl)-N-methylpropanamide | 872428-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-hydroxy-N-methoxy-3-(4-methoxyphenyl)-N-methylpropanamide
• CAS: 872428-03-0
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: JEEUJURUQKBVIS-UHFFFAOYSA-N

物化性质

• 沸点：
  371.6±52.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-N-methoxy-3-(4-methoxyphenyl)-N-methylpropanamide 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)pentadec-4-en-3-one
  参考文献：
  名称：

  Elongation of β-hydroxyenones by cross-metathesis

  摘要：

  Enantioenriched aldol products derived from enones are notoriously difficult to prepare due to their sensitivity to retroaldolisation, elimination and the requirement of a large excess of the enone donor for their preparation. However, some success has been obtained for the preparation of aldol products derived from methylvinylketone and penterione using zinc-dinuclear catalysts or catalytic antibodies. Herein, we describe how simple first-generation hydroxyenones can be easily elongated by alkene exchange with structurally diverse olefinic partners in the presence of Ru-based metathesis catalysts allowing for the preparation of aldol products difficult to access by direct aldolisation. The data suggest that even though unprotected aldols are suitable for these cross-metatbesis reactions, silyl-protected beta-hydroxyenones generally afforded the desired elongated products in much higher chemical yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.037
• 作为产物：
  描述：

  (+/-)-ethyl 3-hydroxy-3-(4-methoxyphenyl)propanoate 在 咪唑 、 四丁基氟化铵 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.42h， 生成 3-hydroxy-N-methoxy-3-(4-methoxyphenyl)-N-methylpropanamide
  参考文献：
  名称：

  Synthetic studies towards tragoponol: preparation of a highly functionalized resorcylate

  摘要：

  Studies on the synthesis of racemic tragoponol are described. The western resorcylate unit of tragoponol was efficiently constructed from appropriate diketo-dioxinone and secondary alcohol intermediates using a ketene generation-trapping and aromatization sequence. Further functionalization provided an advanced diketo-dioxinone intermediate which upon desilylation resulted in the formation of a dihydroisocoumarin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.044

文献信息

• Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
  作者：Naoyuki Shimada、Naoya Takahashi、Naoki Ohse、Masayoshi Koshizuka、Kazuishi Makino

  DOI：10.1039/d0cc05630h

  日期：——

  The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B

  描述了使用二硼酸酐酸酐催化剂使用羧酸的催化羟基直接脱水酰胺化直接合成Weinreb酰胺的第一个成功实例。该方法适用于八种α-羟基酮天然产物的简明合成，它们分别为司塔巴星，4-羟基司他巴星，库拉索菌素A和B，茄型酚A和B以及环丁香素B和C。
• Pd(II)-Catalyzed Cascade Wacker−Heck Reaction:  Chemoselective Coupling of Two Electron-Deficient Reactants
  作者：Franck Silva、Maud Reiter、Rebecca Mills-Webb、Marcin Sawicki、Daniel Klär、Nicolas Bensel、Alain Wagner、Véronique Gouverneur

  DOI：10.1021/jo061292a

  日期：2006.10.1

  acrylate, two electron-deficient reactants. With β-hydroxy ynones, this cascade Wacker−Heck process gave access to highly functionalized tri- or tetrasubstituted dihydropyranones featuring an unusual dienic system. For diastereomerically pure and for enantioenriched β-hydroxyynones, these reactions proceed without affecting the stereochemical integrity of the existing stereocenters. In addition, tetrasubstituted

  开发了一种新颖的钯（II）催化的氧羰基钯化工艺，该工艺允许羟基炔酮与丙烯酸乙酯（两种电子不足的反应物）进行精心策划的结合。借助β-羟基炔酮，这种级联的Wacker-Heck工艺可以获得具有独特二烯体系的高度官能化的三或四取代的二氢吡喃酮。对于非对映体纯的和对映体富集的β-羟基炔酮，进行这些反应时不会影响现有立体中心的立体化学完整性。另外，当使用α-羟基炔酮和丙烯酸乙酯作为起始原料时，可以制备四取代的呋喃酮。环化后获得的二氢吡喃酮和呋喃酮是新颖的化合物，
• Elongation of β-hydroxyenones by cross-metathesis
  作者：Franck A. Silva、Véronique Gouverneur

  DOI：10.1016/j.tetlet.2005.10.037

  日期：2005.12

  Enantioenriched aldol products derived from enones are notoriously difficult to prepare due to their sensitivity to retroaldolisation, elimination and the requirement of a large excess of the enone donor for their preparation. However, some success has been obtained for the preparation of aldol products derived from methylvinylketone and penterione using zinc-dinuclear catalysts or catalytic antibodies. Herein, we describe how simple first-generation hydroxyenones can be easily elongated by alkene exchange with structurally diverse olefinic partners in the presence of Ru-based metathesis catalysts allowing for the preparation of aldol products difficult to access by direct aldolisation. The data suggest that even though unprotected aldols are suitable for these cross-metatbesis reactions, silyl-protected beta-hydroxyenones generally afforded the desired elongated products in much higher chemical yields. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthetic studies towards tragoponol: preparation of a highly functionalized resorcylate
  作者：Hideki Miyatake-Ondozabal、Anthony G.M. Barrett

  DOI：10.1016/j.tetlet.2013.05.044

  日期：2013.9

  Studies on the synthesis of racemic tragoponol are described. The western resorcylate unit of tragoponol was efficiently constructed from appropriate diketo-dioxinone and secondary alcohol intermediates using a ketene generation-trapping and aromatization sequence. Further functionalization provided an advanced diketo-dioxinone intermediate which upon desilylation resulted in the formation of a dihydroisocoumarin. (C) 2013 Elsevier Ltd. All rights reserved.