1,4-dihydro-1,4-methano-naphthalene-5,8-dione | 98053-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-dihydro-1,4-methano-naphthalene-5,8-dione
• 英文别名: 1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthracene-9,10-dione；9.10-Dioxo-1.4;5.8-dimethylen-1.4.5.8.9.10.11.12-oktahydro-anthracen；1,4,4a,5,8,9a-Hexahydro-1,4;5,8-dimethano-anthracen-9,10-dion；Pentacyclo[10.2.1.15,8.02,11.04,9]hexadeca-2(11),6,13-triene-3,10-dione
• CAS: 98053-08-8；110848-96-9
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: QPPBBTNCZJVRRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-1,4-methano-naphthalene-5,8-dione 在 四氯化钛 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以77%的产率得到1α,4α,4aβ,10aβ,5α,8α,8aβ,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione
  参考文献：
  名称：

  异苯并呋喃与受约束的模板的环加成反应带有相邻的亲二烯体。

  摘要：

  五环二烯-二酮1的高产率合成使其能够研究与异苯并呋喃在Diels-Alder [4 + 2]环加成反应中作为双亲二烯体的反应性，从而产生新颖且高度对称的三面空洞体3和4。

  DOI：

  10.1002/chem.200204619
• 作为产物：
  描述：

  norbornenoquinone 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铁 作用下， 以 乙醚 、 乙醇 、 苯 为溶剂， 反应 171.0h， 生成 1,4-dihydro-1,4-methano-naphthalene-5,8-dione
  参考文献：
  名称：

  异苯并呋喃与受约束的模板的环加成反应带有相邻的亲二烯体。

  摘要：

  五环二烯-二酮1的高产率合成使其能够研究与异苯并呋喃在Diels-Alder [4 + 2]环加成反应中作为双亲二烯体的反应性，从而产生新颖且高度对称的三面空洞体3和4。

  DOI：

  10.1002/chem.200204619

文献信息

• Oxidative Diels–Alder reaction of 2,5-dihydroxybenzoic acid with 1,3-cyclopentadiene
  作者：Davood Nematollahi、Adel Ghorbani、Amene Amani、Hamid Salehzadeh、Hadi Beiginejad

  DOI：10.1016/j.cclet.2013.01.040

  日期：2013.3

  The electrochemical oxidation of 2,5-dihydroxybenzoic acid (1) has been studied in the presence of 1,3-cyclopentadiene (2) as a diene in water/ethanol (40/60, v/v) mixture using cyclic voltammetry and controlled-potential coulometry. A plausible mechanism for the oxidation of 1 in the presence of 2 is presented. Compound I was converted into bis-adduct 5 via electrooxidation, Diels-Alder reaction of 2 to anodically generated 3,6-dioxocyclohexa-1,4-dienecarboxylic acid (1ox), decarboxylation reaction, electrooxidation and Diels-Alder reaction. The electrochemical synthesis of 5 was performed in a one-pot reaction, without toxic reagents, at a carbon electrode in a simple cell using an environmentally friendly method. (C) 2013 Davood Nematollahi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved,
• MOLECULAR TWEEZERS FOR THE TREATMENT OF AMYLOID-RELATED DISEASES
  申请人：Bitan Gal

  公开号：US20120108548A1

  公开（公告）日：2012-05-03

  This invention provides novel compositions to inhibit the aggregation of amyloid proteins. In various embodiments the compositions comprise a molecular tweezers that binds lysine and/or arginine and thereby inhibits the aggregation of amyloidogenic proteins.
• Cycloadditions of Isobenzofuran to a Constrained Template Bearing Neighboring Dienophiles
  作者：Martin J. Stoermer、Douglas N. Butler、Ronald N. Warrener、K. D. V. Weerasuria、David P. Fairlie

  DOI：10.1002/chem.200204619

  日期：2003.5.9

  A high yielding synthesis of the pentacyclic diene-dione 1 has enabled investigation of its reactivity as a double dienophile in Diels-Alder [4+2] cycloadditions with isobenzofuran, leading to novel and highly symmetrical three-sided cavitands 3 and 4.

  五环二烯-二酮1的高产率合成使其能够研究与异苯并呋喃在Diels-Alder [4 + 2]环加成反应中作为双亲二烯体的反应性，从而产生新颖且高度对称的三面空洞体3和4。