methyl γ-[(2-phenylethenyl)methoxy]acetoacetate | 99522-50-6

• 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 γ-[(2-phenylethenyl)methoxy]acetoacetate
• 英文别名: methyl 4(E)-cinnamyloxyacetoacetate；methyl 3-oxo-4-[(E)-3-phenylprop-2-enoxy]butanoate
• CAS: 99522-50-6
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: KFKWTPIAJKNRDU-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl γ-[(2-phenylethenyl)methoxy]acetoacetate 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 以98%的产率得到methyl γ-(2-phenylethenyl)methoxy-α-diazo-β-ketoester
  参考文献：
  名称：

  Ruthenium(II) Porphyrin Catalyzed Formation of (Z)-4-Alkyloxycarbonyl- methylidene-1,3-dioxolanes from γ-Alkoxy-α-diazo-β-ketoesters

  摘要：

  [GRAPHICS]Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of gamma-alkoxy-alpha-diazo-beta-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [Ru-II(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.

  DOI：

  10.1021/ol010283f
• 作为产物：
  描述：

  4-溴-3-氧代-丁酸甲酯 、 3-苯基丙-2-烯-1-醇 在 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以56%的产率得到methyl γ-[(2-phenylethenyl)methoxy]acetoacetate
  参考文献：
  名称：

  Ruthenium(II) Porphyrin Catalyzed Formation of (Z)-4-Alkyloxycarbonyl- methylidene-1,3-dioxolanes from γ-Alkoxy-α-diazo-β-ketoesters

  摘要：

  [GRAPHICS]Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of gamma-alkoxy-alpha-diazo-beta-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [Ru-II(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.

  DOI：

  10.1021/ol010283f

文献信息

• ENANTIOSELECTIVE CROSS DEHYDROGENATIVE COUPLING REACTIONS AND COMPOUNDS SYNTHESIZED BY THE REACTIONS
  申请人：Northwestern University

  公开号：US20200181106A1

  公开（公告）日：2020-06-11

  Disclosed are enantioselective cross dehydrogenative coupling reactions for synthesizing tetrahydropyran compounds. Novel tetrahydropyran compounds may be synthesized by the disclosed methods as well as tetrahydropyran precursor compounds for synthesizing various naturally occurring compounds. The enantioselective cross dehydrogenative coupling reactions utilize in situ Lewis Acid activation in combination with oxidative formation of an oxocarbenium ion to provide a highly efficient and selective coupling reaction for synthesizing tetrahydropyran compounds.

  揭示了用于合成四氢吡喃化合物的对映选择性交叉脱氢偶联反应。根据所披露的方法可以合成新型四氢吡喃化合物，以及用于合成各种天然存在化合物的四氢吡喃前体化合物。对映选择性交叉脱氢偶联反应利用原位Lewis酸活化结合氧化形成氧杂环丙阳离子，提供了一种高效且选择性的偶联反应，用于合成四氢吡喃化合物。
• Novel dihydropyridine derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05034395A1

  公开（公告）日：1991-07-23

  Dihydropyridine derivatives and salts thereof represented by the general formula, ##STR1## which possess excellent calcium antagonist effect, hypotensive effect, platelets aggregation inhibitory effect, phosphodiesterase inhibitory effect, calmodulin inhibitory effect and peroxidized lipid lowering effect, and thus dihydropyridine derivatives and salts thereof are useful as a coronary blood flow improving agent such as coronary vasodilator, hypotensive agent, prophylaxis and treating agents for thrombosis, phophodiesterase inhibitory agent, peroxidized lipid metabolism lowering agent, anti-inflammatory agent and others.

  二氢吡啶衍生物及其盐，由一般式##STR1##表示，具有优异的钙拮抗剂作用、降压作用、血小板聚集抑制作用、磷酸二酯酶抑制作用、钙调蛋白抑制作用和过氧化脂质降低作用。因此，二氢吡啶衍生物及其盐可用作冠状动脉血流改善剂，如冠状动脉扩张剂、降压剂、预防和治疗血栓的药物、磷酸二酯酶抑制剂、过氧化脂质代谢降低剂、抗炎剂等。
• Dihydropyridine derivatives and process for preparing the same
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05137889A1

  公开（公告）日：1992-08-11

  Dihydropyridine derivatives and salts thereof represented by the general formula, ##STR1## which possess excellent calcium antagonist effect, hypotensive effect, platelets aggregation inhibitory effect, phosphodiesterase inhibitory effect, calmodulin inhibitory effect and peroxidized lipid lowering effect, and thus dihydropyridine derivatives and salts thereof are useful as a coronary blood flow improving agent such as coronary vasodilator, hypotensive agent, prophylaxis and treating agents for thrombosis, phosphodiesterase inhibitory agent, peroxidized lipid metabolism lowering agent, anti-inflammatory agent and others.

  通式为##STR1##的二氢吡啶衍生物及其盐具有出色的钙拮抗作用、降压作用、抑制血小板聚集作用、磷酸二酯酶抑制作用、钙调蛋白抑制作用和过氧化脂质降低作用，因此二氢吡啶衍生物及其盐可用作冠状动脉血流改善剂，如冠状动脉扩张剂、降压剂、预防和治疗血栓的药物、磷酸二酯酶抑制剂、过氧化脂质代谢降低剂、抗炎剂等。
• Novel dihydropyridine derivatives and process for preparing the same
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0145434A2

  公开（公告）日：1985-06-19

  Dihydropyridine derivatives and salts thereof represented by the general formula, which possess excellent calcium antagonist effect, hypoten- sive effect, platelets aggregation inhibitory effect, phosphodiesterase inhibitory effect, calmodulin inhibitory effect and peroxidized lipid lowering effect, and thus dihydropyridine derivatives and salts thereof are useful as a coronary blood flow improving agent such as coronary vasodilator, hypotensive agent, prophylaxis and treating agents for thrombosis, phosphodiesterase inhibitory agent, peroxidized lipid metabolism lowering agent, anti-inflammatory agent and others.

  通式代表的二氢吡啶衍生物及其盐、 具有良好的钙拮抗剂作用、降血压作用、血小板聚集抑制作用、磷酸二酯酶抑制作用、钙调素抑制作用和过氧化脂质降低作用、因此，二氢吡啶衍生物及其盐类可用作冠状动脉血流改善剂，如冠状动脉血管扩张剂、降血压剂、血栓预防和治疗剂、磷酸二酯酶抑制剂、过氧化脂质代谢降低剂、消炎剂等。
• Enantioselective cross dehydrogenative coupling reactions and compounds synthesized by the reactions
  申请人：Northwestern University

  公开号：US11174238B2

  公开（公告）日：2021-11-16

  Disclosed are enantioselective cross dehydrogenative coupling reactions for synthesizing tetrahydropyran compounds. Novel tetrahydropyran compounds may be synthesized by the disclosed methods as well as tetrahydropyran precursor compounds for synthesizing various naturally occurring compounds. The enantioselective cross dehydrogenative coupling reactions utilize in situ Lewis Acid activation in combination with oxidative formation of an oxocarbenium ion to provide a highly efficient and selective coupling reaction for synthesizing tetrahydropyran compounds.

  公开了用于合成四氢吡喃化合物的对映体选择性交叉脱氢偶联反应。通过所公开的方法可以合成新型四氢吡喃化合物以及用于合成各种天然化合物的四氢吡喃前体化合物。对映选择性交叉脱氢偶联反应利用原位路易斯酸活化与氧化形成的氧羰基鎓离子相结合，为合成四氢吡喃化合物提供了一种高效和选择性的偶联反应。