1,4,5,8-tetrahydro-1t,4t,5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester | 10152-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1,4,5,8-tetrahydro-1t,4t,5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester
• 英文别名: 1,4,5,8-tetrahydro-1t,4t;5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester；1,4,5,8-Tetrahydro-1t,4t;5t,8t-diepoxido-naphthalin-4ar,8ac-dicarbonsaeure-dimethylester
• CAS: 10152-89-3；25860-27-9
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: GLEMMZWXHHUZFE-LKVBVQDXSA-N

物化性质

• 沸点：
  366.5±42.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,4,5,8-tetrahydro-1t,4t,5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以79%的产率得到(1α,4α,4aβ,5α,8α,8aβ)-1,4,5,8-tetrahydro-1,4:5,8-diepoxynaphthalene-4a,8a-dimethanol
  参考文献：
  名称：

  Some Transformations of Adducts of 3,6-Dimethoxy-4,5-methylenedioxy-1,2-didehydrobenzene and Furans. An Approach to the 5,8-Dimethoxy-6,7-methylenedioxynaphtho[2,3-c]furan-4,9-dione Ring System of Ventilone A

  摘要：

  由芳香族化合物衍生的加合物 3,6-二甲氧基-4,5-亚甲二氧基-1,2-二脱氢苯 (19) 与呋喃和 和 2-甲氧基呋喃的加合物已转化为 5,8-二甲氧基-6,7-亚甲二氧基-1,2-萘醌 (22) 和 5,8-二甲氧基-6,7-亚甲二氧基-1,4-萘醌（24）。在 (19)与 1H,3H-furo[3,4-c]furan (38)产生了不稳定的加合物(37)。 氧化后转化为 5,8-二甲氧基-6,7-亚甲二氧基萘并[2,3-c]呋喃-4,9-二酮（36 (36)，这是一种具有天然醌环系统的化合物 文替龙 A。

  DOI：

  10.1071/c97209
• 作为产物：
  描述：

  重氮甲烷 、 (1R,4S,4aS,5R,8S,8aS)-1,4,4a,5,8,8a-hexahydro-1,4:5,8-diepoxynaphthalene-4a,8a-dicarboxylic acid 在 甲醇 、 乙醚 作用下， 生成 1,4,5,8-tetrahydro-1t,4t,5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  呋喃和乙炔二羧酸的狄尔斯-阿尔德加合物的构型

  摘要：

  呋喃和乙炔二羧酸的 Diels-Alder 加合物 (I) 的构型是通过化学和光谱方法建立的，并被发现是 exo-exo (IIa)。

  DOI：

  10.1139/v66-185

文献信息

• Influence of Lewis Acids on the Diels–Alder Reaction. V. The Reaction of Furan with Dimethyl Acetylenedicarboxylate
  作者：A.W. McCulloch、D. G. Smith、A. G. McInnes

  DOI：10.1139/v73-617

  日期：1973.12.15

  The Diels–Alder addition of furan to dimethyl acetylenedicarboxylate (DMAD) affords a monoadduct 1. The position and steric course of further addition of furan to the latter are temperature dependent. At temperatures of 50° or below addition occurs mainly at the activated double bond to give endo-endo4 and endo-exo5 diadducts. At 100° addition occurs at the less substituted double bond of the monoadduct to give analogous endo-endo7 and endo-exo9 diadducts; further addition of furan to the latter at 100° affords four triadducts 12–15. The configurations of all these products were determined by p.m.r. and assignments confirmed by simulation of the spectra.AlCl₃ causes enormous rate enhancement of the Diels–Alder additions of furan to DMAD and to the activated double bond of the monoadduct. In the presence of the Lewis acid the predominant diadduct formed is the endo-exo isomer 5.

  呋喃与二甲基乙炔二羧酸酯（DMAD）的Diels-Alder加成生成单加合物1。后续的呋喃加成位置和立体位阻取决于温度。在50℃以下的温度下，加成主要发生在活化的双键上，生成内内型4和内外型5的二加合物。在100℃时，加成发生在单加合物中较不取代的双键上，生成类似的内内型7和内外型9的二加合物；在100℃下，进一步的呋喃加成形成四种三加合物12-15。所有这些产物的构型都由p.m.r.确定，通过模拟光谱进行确认。AlCl3可以极大地增强呋喃与DMAD以及单加合物上活化的双键的Diels-Alder加成速率。在路易斯酸的存在下，主要形成内外型异构体5的二加合物。
• Diels; Alder, Justus Liebigs Annalen der Chemie, 1931, vol. 490, p. 257,263
  作者：Diels、Alder

  DOI：——

  日期：——
• Clay-catalyzed solventless addition reactions of furan with α,β-unsaturated carbonyl compounds
  作者：Martín Avalos、Reyes Babiano、JoséL. Bravo、Pedro Cintas、JoséL. Jiménez、Juan C. Palacios

  DOI：10.1016/s0040-4039(98)02091-7

  日期：1998.12

  The reaction of furan with alpha,beta-unsaturated carbonyl dienophiles catalyzed by K10 montmorillonite in the absence of organic solvents produces the corresponding Diels-Alder adducts and, in the case of methyl vinyl ketone, Michael-type products, under much milder conditions than the conventional protocols. The results are consistent with acid catalysis on the clay surface. Acrylates gave lower yields and/or decomposition products. The reaction can be extended to alkynic substrates such as DMAD to afford cycloadducts in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• The synthesis of polarofacial spacer molecules: a new twist in the coupling of ring strained olefins with oxadiazoles.
  作者：Ronald N. Warrener、Douglas N. Butler、Wen Yan Liao、Ian G. Pitt、Richard A. Russell

  DOI：10.1016/s0040-4039(00)85989-4

  日期：1991.4

  New approaches to the synthesis of rigid spacer molecules in which an oxygen-bridge bestows the facial polarity is described: attempts to couple 7-oxanorbornenes together using 1,3,4-oxadiazoles yields inverted, non linear products in a stereospecific reaction which differs significantly from that known to obtain with norbornenes.
• Jurczak, Janusz; Belniak, Stanislaw; Kozluk, Tomasz, Bulletin of the Polish Academy of Sciences: Chemistry, 1984, vol. 32, # 3-6, p. 135 - 141
  作者：Jurczak, Janusz、Belniak, Stanislaw、Kozluk, Tomasz、Pikul, Stanislaw、Salanski, Piotr

  DOI：——

  日期：——