dimethyl (1R,21S,22S,23S,25R,26R)-5,8,11,14,17,24,27-heptaoxahexacyclo[19.5.1.02,20.04,18.022,26.023,25]heptacosa-2,4(18),19-triene-23,25-dicarboxylate | 192874-63-8

• 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: dimethyl (1R,21S,22S,23S,25R,26R)-5,8,11,14,17,24,27-heptaoxahexacyclo[19.5.1.02,20.04,18.022,26.023,25]heptacosa-2,4(18),19-triene-23,25-dicarboxylate
• CAS: 192874-63-8
• 化学式: C₂₄H₂₈O₁₁
• 分子量: 492.48
• InChiKey: PLDVUMMKKAWOGV-CYJZIJFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1α,4α,4aβ,10aβ,5α,8α,8aβ,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione 、 dimethyl (1R,21S,22S,23S,25R,26R)-5,8,11,14,17,24,27-heptaoxahexacyclo[19.5.1.02,20.04,18.022,26.023,25]heptacosa-2,4(18),19-triene-23,25-dicarboxylate 以56%的产率得到
  参考文献：
  名称：

  Building BLOCK Strategies for the Synthesis of Molecular Clefts with Inside Functionality

  摘要：

  A new general route to U-type cavity structures (molecular clefts) with inside functionality has been developed using wall extension or base/ roof assembly methods which draw upon (i) the 1,3 dipolar cycloaddition reaction between alkenes and cyclobutene epoxides (ACE coupling) or (ii) the Diels-Alder reaction of alkenes with fused dihydropyridazines (s-tetrazine coupling). In this way, functional units (e.g., crown ethers, redox active naphthalenes) have been attached stereospecifically to short-walled bis-alkenes 1-5 to produce cavity structure 6-10 with top of-wall separations (C to C) from 4.5 to 12.7 Angstrom.

  DOI：

  10.1021/ol9905396
• 作为产物：
  描述：

  丁炔二酸二甲酯 在 钌 叔丁基过氧化氢 、 甲基锂 作用下， 反应 2.0h， 生成 dimethyl (1R,21S,22S,23S,25R,26R)-5,8,11,14,17,24,27-heptaoxahexacyclo[19.5.1.02,20.04,18.022,26.023,25]heptacosa-2,4(18),19-triene-23,25-dicarboxylate
  参考文献：
  名称：

  Building BLOCK Strategies for the Synthesis of Molecular Clefts with Inside Functionality

  摘要：

  A new general route to U-type cavity structures (molecular clefts) with inside functionality has been developed using wall extension or base/ roof assembly methods which draw upon (i) the 1,3 dipolar cycloaddition reaction between alkenes and cyclobutene epoxides (ACE coupling) or (ii) the Diels-Alder reaction of alkenes with fused dihydropyridazines (s-tetrazine coupling). In this way, functional units (e.g., crown ethers, redox active naphthalenes) have been attached stereospecifically to short-walled bis-alkenes 1-5 to produce cavity structure 6-10 with top of-wall separations (C to C) from 4.5 to 12.7 Angstrom.

  DOI：

  10.1021/ol9905396

文献信息

• A new building block technique based on cycloaddition chemistry for the regiospecific linking of alicyclic sub-units as a route to large, custom-functionalised structures
  作者：Ronald N. Warrener、Austin C. Schultz、Douglas N. Butler、Shudong Wang、Indu B. Mahadevan、Richard A. Russell

  DOI：10.1039/a700010c

  日期：——

  A new building BLOCK approach to synthesis has been developed where functionalised norbornenes (BLOCK A) are coupled with functionalised cyclobutene epoxides (BLOCK B) to produce A + B structures of defined geometry; use of a dual (spacer) BLOCK allows the formation of large structures where crown ether, ligand and redox centres are incorporated in similar or mixed pairings.

  一种新的合成方法（BLOCK）已经开发出来，其中，官能化的降冰片烯（BLOCK A）与官能化的环丁烯环氧化物（BLOCK B）结合，形成具有特定几何形状的A + B结构；使用双（间隔）BLOCK可以形成大型结构，其中，冠醚、配体和氧化还原中心以相似或混合配对的形式结合在一起。
• Building BLOCK Strategies for the Synthesis of Molecular Clefts with Inside Functionality
  作者：Ronald N. Warrener、Davor Margetic、Ananda S. Amarasekara、Douglas N. Butler、Indu B. Mahadevan、Richard A. Russell

  DOI：10.1021/ol9905396

  日期：1999.7.1

  A new general route to U-type cavity structures (molecular clefts) with inside functionality has been developed using wall extension or base/ roof assembly methods which draw upon (i) the 1,3 dipolar cycloaddition reaction between alkenes and cyclobutene epoxides (ACE coupling) or (ii) the Diels-Alder reaction of alkenes with fused dihydropyridazines (s-tetrazine coupling). In this way, functional units (e.g., crown ethers, redox active naphthalenes) have been attached stereospecifically to short-walled bis-alkenes 1-5 to produce cavity structure 6-10 with top of-wall separations (C to C) from 4.5 to 12.7 Angstrom.