methyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate | 118741-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate
• 英文别名: methyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)but-2-ynoate
• CAS: 118741-64-3
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: VITSOENRLLGMTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 生成 methyl 4-oxo-4-(3,4,5-trimethoxyphenyl)but-2-ynoate
  参考文献：
  名称：

  Synthesis of Fluorenone and Anthraquinone Derivatives from Aryl- and Aroyl-Substituted Propiolates

  摘要：

  Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Die Is Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.

  DOI：

  10.1021/ol4023276
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 丙炔酸甲酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 methyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate
  参考文献：
  名称：

  Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates

  摘要：

  The At(I)-catalyzed regioselective hydration of gamma-acetoxy-alpha,beta-acetylinic ester by the assistance of a neighboring carbonyl group has beets developed. Varieties of simple primary, secondary, and tertiary gamma-acetoxy-alpha,beta-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding beta-keto esters. The reaction' tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. O-18 labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.

  DOI：

  10.1021/acs.joc.5b00400

文献信息

• Propiolophenone derivatives
  申请人：Hoffman-La Roche Inc.

  公开号：US04929741A1

  公开（公告）日：1990-05-29

  Propiolophenone derivatives of the formula ##STR1## wherein R.sup.6 is hydrogen, lower alkyl or a group of the formula ##STR2## as well as corresponding hydroxy compounds of the formula ##STR3## wherein R.sup.6' is hydrogen, lower alkyl, a group of formula (a), (b), (c), (d) or (e) or a group of the formula --C(R.sup.14)(R.sup.15)OR.sup.16' (f'): exhibit mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers and/or duodenal ulcers.

  式（I）的丙烯酰苯酮衍生物，其中R.sup.6为氢，低碳基或式（II）的基团，以及式（III）的相应羟基化合物，其中R.sup.6'为氢，低碳基，式（a），（b），（c），（d）或（e）的基团或式的基团--C(R.sup.14)(R.sup.15)OR.sup.16'（f'）：表现出粘膜保护和/或抑制胃酸分泌的特性，因此可以用于控制或预防胃肠道疾病，特别是对抗胃溃疡和/或十二指肠溃疡。
• US4929741A
  申请人：——

  公开号：US4929741A

  公开（公告）日：1990-05-29
• Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates
  作者：Tapas R. Pradhan、Kishor L. Mendhekar、Debendra K. Mohapatra

  DOI：10.1021/acs.joc.5b00400

  日期：2015.6.5

  The At(I)-catalyzed regioselective hydration of gamma-acetoxy-alpha,beta-acetylinic ester by the assistance of a neighboring carbonyl group has beets developed. Varieties of simple primary, secondary, and tertiary gamma-acetoxy-alpha,beta-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding beta-keto esters. The reaction' tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. O-18 labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.
• Synthesis of Fluorenone and Anthraquinone Derivatives from Aryl- and Aroyl-Substituted Propiolates
  作者：Florian Pünner、Justin Schieven、Gerhard Hilt

  DOI：10.1021/ol4023276

  日期：2013.9.20

  Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Die Is Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.