4,5-dimethyl-3,6-dihydro-pyran-2,2-dicarboxylic acid diethyl ester | 24588-60-1

• 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-pyran-2,2-dicarboxylic acid diethyl ester
• 英文别名: 4,5-Dimethyl-3,6-dihydro-pyran-2,2-dicarbonsaeure-diaethylester；3,6-dihydro-4,5-dimethyl-2H-pyran-2,2-dicarboxylic acid diethyl ester；diethyl 3,6-dihydro-4,5-dimethyl-2H-pyran-2,2-dicarboxylate；2H-Pyran-2,2-dicarboxylic acid, 3,6-dihydro-4,5-dimethyl-, diethyl ester；diethyl 3,4-dimethyl-2,5-dihydropyran-6,6-dicarboxylate
• CAS: 24588-60-1
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: NWTYARCPCYPHDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-3,6-dihydro-pyran-2,2-dicarboxylic acid diethyl ester 在 platinum on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 2,2-dicarboethoxy-cis-4,5-dimethyltetrahydropyran
  参考文献：
  名称：

  Carbon-13 NMR spectra of saturated heterocycles: XI—Tetrahydropyrans (oxanes)

  摘要：

  AbstractThe 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without methyl substituents at various ring positions, some of them bearing in addition (or instead) ethyl, vinyl, ethynyl, carbomethoxy and methylol substituents at C‐2, have been recorded, and the 294 resulting chemical shifts have been correlated by multiple linear regression analysis. Axial and equatorial α‐, β‐, γ‐, δ‐, gem‐ and vic‐parameters for shifts caused by methyl groups at all ring positions, and similar parameters for Et,—CHCH2,—CCH, CO2Me and CH2OH groups at C‐2, are reported. Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and experimental shifts is excellent. This is probably the largest parameter set of this type extant. 13C NMR spectra of a number of additional substituted tetrahydropyrans, and of 3,6‐dihydro‐2H‐pyrans and 3,4‐dihydro‐2H‐pyrans, are tabulated and discussed.

  DOI：

  10.1002/omr.1270210205
• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 酮基丙二酸二乙酯 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 正戊烷 为溶剂， 反应 72.0h， 以78%的产率得到4,5-dimethyl-3,6-dihydro-pyran-2,2-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Le Triflate de Bismuth(III) Comme Catalyseur Dans la Reaction de Carbonyl-Diels-Alder

  摘要：

  在三氟甲磺酸铋 (III) 存在下，羰基化的亲电子试剂（甲基草酸乙酯或乙醛酸乙酯）和普通二烯选择性地（60-100）导致杂羰基-Diels-Alder 反应与烯反应产物。Bi(OTf) 3 表现出很强的催化活性并且在温和的条件下反应。En présence de triflate de bismuth(III) le mésoxalate et le glyoxylate d'éthyle réagissent avec des diènes usuels pour donner un mélange de carbonyl-Diels-Alder et du produit de la ène réaction。Bi(OTf) 3 présente une forte activité catalytique et réagit dans des conditions douces。

  DOI：

  10.1080/10426500210673

文献信息

• Derivatives of cyclic ethers and sulfides for the treatment of
  申请人：The Du Pont Merck Pharmaceutical Company

  公开号：US05491152A1

  公开（公告）日：1996-02-13

  The present invention provides compounds of Formula I, ##STR1## or a pharmaceutically acceptable salt forms thereof, which are inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.

  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。
• The carbonyl-Diels-Alder reaction catalyzed by bismuth (III) chloride
  作者：Hélène Robert、Bernard Garrigues、Jacques Dubac

  DOI：10.1016/s0040-4039(97)10791-2

  日期：1998.3

  In presence of bismuth (III) chloride, a carbonylated electrophile (ethyl mesoxalate or glyoxylate) and usual diene led selectively (65 to 100%) the hetero carbonyl-Diels-Alder reaction with the ene reaction product. BiCl3 exhibits strong catalytic activity and, compared with previous literature, reacts under mild conditions.

  在氯化铋（III）的存在下，羰基化的亲电试剂（中草酸乙酯或乙醛酸乙酯）和通常的二烯选择性地（65％至100％）导致杂羰基-Diels-Alder反应与烯反应产物。BiCl 3表现出很强的催化活性，并且与以前的文献相比，在温和的条件下反应。
• 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.
• 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：——