4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylic acid | 27944-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylic acid
• 英文别名: 4,5-Dimethyl-3,6-dihydro-2H-pyran-2-carbonsaeure；3,6-dihydro-4,5-dimethyl-2H-pyran-2-carboxylic acid；4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylic acid
• CAS: 27944-71-4
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: GOIQIMNZKRMLRS-UHFFFAOYSA-N

物化性质

• 沸点：
  282.2±40.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes

  摘要：

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.

  DOI：

  10.1016/0968-0896(96)00143-5
• 作为产物：
  描述：

  4,5-dimethyl-3,6-dihydro-pyran-2,2-dicarboxylic acid diethyl ester 在 吗啉 、 氢氧化钾 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 22.0h， 生成 4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes

  摘要：

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.

  DOI：

  10.1016/0968-0896(96)00143-5
• 作为试剂：
  描述：

  草酰氯 、 6-甲基-2,4-双(甲基硫代)-3-吡啶胺 在 三乙胺 作用下， 以 四氢呋喃 、 N-甲基乙酰胺 、 4,5-dimethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 、 苯 为溶剂， 生成 N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]-2,3-dihydro-4,5-dimethyl-2H-pyran-2-carboxamide
  参考文献：
  名称：

  Derivatives of cyclic ethers and sulfides for the treatment of

  摘要：

  本发明提供了公式I的化合物，或者是其药用可接受的盐形式，这些化合物是酰辅酶A：胆固醇O-酰基转移酶（ACAT）的抑制剂，包含此类化合物的药物组合物，制备此类化合物的方法，以及将这些化合物用作抗高胆固醇血症和/或抗动脉粥样硬化剂的用途。

  公开号：

  US05491152A1

文献信息

• Enhancement of Dienophilic and Enophilic Reactivity of the Glyoxylic Acid by Bismuth(III) Triflate in the Presence of Water
  作者：H. Laurent-Robert、C. Le Roux、J. Dubac

  DOI：10.1055/s-1998-1869

  日期：1998.10

  Bismuth(III) trifluoromethanesulfonate (1) is found to efficiently catalyze carbonyl-Diels-Alder or carbonyl-ene reactions between glyoxylic acid and classical dienes or substituted olefins, in the presence of water.

  三氟甲烷磺酸铋(III)（1）在水的存在下，能够高效催化羟基乙酸与经典二烯或取代烯烃之间的羰基-达尔斯-阿尔德反应或羰基-烯反应。
• Achmatowicz; Zamojski, Croatica Chemica Acta, 1957, vol. 29, p. 269,272
  作者：Achmatowicz、Zamojski

  DOI：——

  日期：——
• Garrigues, Bernard; Laurent, Regis; Laporte, Christian, Liebigs Annalen, 1996, # 5, p. 743 - 744
  作者：Garrigues, Bernard、Laurent, Regis、Laporte, Christian、Laporterie, Andre、Dubac, Jacques

  DOI：——

  日期：——
• US5491152A
  申请人：——

  公开号：US5491152A

  公开（公告）日：1996-02-13
• ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes
  作者：Richard G. Wilde、Jeffrey T. Billheimer、Sandie J. Germain、Elizabeth A. Hausner、Paul C. Meunier、Deborah A. Munzer、Janet K. Stoltenborg、Peter J. Gillies、Deborah L. Burcham、Shiew-Mai Huang、John D. Klaczkiewicz、Soo S. Ko、Ruth R. Wexler

  DOI：10.1016/0968-0896(96)00143-5

  日期：1996.9

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.