(1R,4S,4aS,5S,5aR,6S,13R,13aS,14R,14aR)-7,12-dimethoxy-1,4,4a,5a,6,13,13a,14a-octahydro-5,14-epoxy-1,4:6,13-dimethanopentacene-5,14-dicarbonyl dichloride | 291761-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (1R,4S,4aS,5S,5aR,6S,13R,13aS,14R,14aR)-7,12-dimethoxy-1,4,4a,5a,6,13,13a,14a-octahydro-5,14-epoxy-1,4:6,13-dimethanopentacene-5,14-dicarbonyl dichloride
• CAS: 291761-79-0
• 化学式: C₂₈H₂₄Cl₂O₅
• 分子量: 511.402
• InChiKey: MAKJJRWAUCNNOS-SZKRCHNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aS,5S,5aR,6S,13R,13aS,14R,14aR)-7,12-dimethoxy-1,4,4a,5a,6,13,13a,14a-octahydro-5,14-epoxy-1,4:6,13-dimethanopentacene-5,14-dicarbonyl dichloride 生成
  参考文献：
  名称：

  New and improved ‘LEGO’ BLOCK protocols for the direct synthesis of hydrophilic ribbon molecules with acid, ester or peptide functionality

  摘要：

  Hydrophilic ribbon molecules are produced directly from the reaction of cyclobutene epoxide BLOCKs with norbornene dipolarophiles or indirectly by chemical modification of substituents in preformed lipophilic ribbon molecules. The formation of di- and tetra-acid chloride epoxides holds the key to the formation of ester, acid and amide BLOCKs which are active in 1,3-dipolar cycloadditions with norbornene dipolarophiles, thereby delivering a wide range of substituents into the ribbon molecules and opening up combinatorial opportunities at each step. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00685-7
• 作为产物：
  描述：

  (1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarboxylic acid 在 叔丁基过氧化氢 、 草酰氯 、 potassium tert-butylate 作用下， 生成 (1R,4S,4aS,5S,5aR,6S,13R,13aS,14R,14aR)-7,12-dimethoxy-1,4,4a,5a,6,13,13a,14a-octahydro-5,14-epoxy-1,4:6,13-dimethanopentacene-5,14-dicarbonyl dichloride
  参考文献：
  名称：

  New and improved ‘LEGO’ BLOCK protocols for the direct synthesis of hydrophilic ribbon molecules with acid, ester or peptide functionality

  摘要：

  Hydrophilic ribbon molecules are produced directly from the reaction of cyclobutene epoxide BLOCKs with norbornene dipolarophiles or indirectly by chemical modification of substituents in preformed lipophilic ribbon molecules. The formation of di- and tetra-acid chloride epoxides holds the key to the formation of ester, acid and amide BLOCKs which are active in 1,3-dipolar cycloadditions with norbornene dipolarophiles, thereby delivering a wide range of substituents into the ribbon molecules and opening up combinatorial opportunities at each step. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00685-7

文献信息

• Container Systems II: An Experimental Study of the High-Pressure Intramolecular Cycloaddition of Tethered Furans and Anthracenes onto Norbornane Cyclobutene-1,2-diesters
  作者：Davor Margetić、Ronald N. Warrener

  DOI：10.1002/jhet.2015

  日期：2014.9

  single 1:1‐adduct was obtained in which one furfuryl moiety was intramolecularly cyclized and the other present as the DMAD adduct; again this product underwent retro‐DA reaction at 40°C. Similar intermolecular cyclization was observed with the bis‐anthracenyl esters. The stereoselectivity of the intermolecular attack of the furfuryl diene with the dienophilic cyclobutene gave a single adduct by endo‐face

  描述了一种新型的容器分子，并报道了产生原型的第一步。该方法的中心是在末端的环丁烯-1，2-二糠基酯或在中央降冰片烷亚基的桥头处具有类似官能团的聚降冰片烷的形成。描述了糠基起始原料及其蒽基对应物的合成。转换为容器系统涉及糠醛或蒽的分子间连接，方法是在Diels-Alder（DA）方案中，在热或高压（HP）条件下，用二甲基乙炔二甲酸二甲酯（DMAD）处理。实际上，降冰片烷底物之间没有发生分子间连接，仅产生了DA 1：1加DMAD的产物。在高压条件下检测到糠基单元之一在环丁烯π键上的分子内加成，该分子间产物能够通过在室温或低于室温的条件下进行分离和表征，但在室温以上仍可恢复为起始原料。当在DMAD存在下进行时，获得了一个1：1-加合物，其中一个糠基部分被分子内环化，另一个作为DMAD加合物存在。该产品再次在40°C进行逆转录DA反应。双蒽基酯也观察到类似的分子间环化反应。糠基二烯与双亲亲环丁烯的