dimethyl (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-dicarboxylate | 192874-59-2

• 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 (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-dicarboxylate
• CAS: 192874-59-2
• 化学式: C₂₃H₂₂O₇
• 分子量: 410.423
• InChiKey: NYRWFGBAPTXYCF-BOEMZCLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl (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-dicarboxylate 在 氢氧化钾 、 草酰氯 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (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-dicarbonyl chloride
  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：

  dimethyl-(2aα,3β,10α,10aα)-2a,3,10,10a-tetrahydro-3,10-methano-4,9-dimethoxycyclobuta(b)anthracene-1,2-dicarboxylate 在 丁基氢过氧化物 、 甲基锂 作用下， 生成 dimethyl (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-dicarboxylate
  参考文献：
  名称：

  Molecular topology: The synthesis of a new class of rigid arc-shaped spacer molecules based on syn-facially fused norbornanes and 7-heteronorbornanes in which heterobridges are used to govern backbone curvature

  摘要：

  Norbornadienes and 7-heteronorbornadienes are reacted with 7-oxa (or carba or aza) norbornene-fused cyclobutene epoxides (or aziridines) to produce hetero-bridged polynorbornane cycloadducts containing syn-facially arranged N,O (or C,N or C,O) bridges. New dual cyclobutene epoxides and dual cyclobutene aziridines are used to prepare multi-fused norbornanes having curved topology in which the heteroatoms modify the curvature in a predictable way C>N>O; AM1 modelling; of representative: [9]polynorbornanes is presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00694-2

文献信息

• Preparation of New Porphyrin blocks and their Application to the Synthesis of Spacer and Cavity Ribbon Structures
  作者：Ronald N. Warrener、Martin R. Johnston、Maxwell J. Gunter

  DOI：10.1055/s-1998-3136

  日期：1998.6

  Fused-norbornene blocks, formed by the condensation of porphyrin vic-diamines with polyalicyclic α-diones, have been used to produce mono-porphyrin systems linked to other effector units or new U-type cavity bis-porphyrins using ACE or s-tetrazine coupling protocols.

  卟啉沧二胺与多脂环δ-±-二酮缩合形成的熔融降冰片烯嵌段，已被用于生产与其他效应单元相连的单卟啉系统，或利用 ACE 或 s-四嗪偶联协议生产新型 U 型空腔双卟啉。
• 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。
• Use of a 9,10-Dihydrofulvalene Pincer Cycloadduct as a Cornerstone for Molecular Architecture
  作者：Mirta Golić、Martin R. Johnston、Davor Margetić、Austin C. Schultz、Ronald N. Warrener

  DOI：10.1071/ch06286

  日期：——

  7a-hexahydro-3,4,7-metheno-7H-cyclopenta[a]pentalene-7,8-dicarboxylate (3, a 9,10-dihydrofulvalene pincer cycloadduct) was found to be a versatile building block for the synthesis of polynorbornyl scaffolds containing various end functionalities such as porphyrins, pyrimidine, and the phenanthroline ligand in the free and complexed forms. The block is stable under various cycloaddition reaction conditions and

  Dimethyl-3,3a,3b,4,6a,7a-hexahydro-3,4,7-metheno-7H-cyclopenta[a]pentalene-7,8-dicarboxylate（3，一种 9,10-二氢富瓦烯钳形环加合物）是被发现是用于合成聚降冰片基支架的通用结构单元，该支架含有各种末端官能团，例如自由和复合形式的卟啉、嘧啶和菲咯啉配体。该嵌段在各种环加成反应条件下稳定，具有较高的π键反应性。使用基于半经验的方法 (AM1) 的分子建模表明，将这种二烯嵌段掺入聚降冰片基系统对其整体结构具有重要影响。特别是，嵌段的加入导致通常在聚降冰片基分子中观察到的曲率变直，从而形成几乎理想的线性多环刚性间隔物。
• The synthesis of new framework structures containing rigidly-linked pyrimidines suitable for uracil and cytosine elaboration
  作者：Ronald N Warrener、Mirta Golic、Douglas N Butler

  DOI：10.1016/s0040-4039(98)00866-1

  日期：1998.6

  Fused norbornenes and tricyclo[4.2.2.12,5]undec-3,7,9-trienes containing 2,4-dichloropyrimidine and 2,4-dimethoxy pyrimidine units are coupled with norbornadiene, benzonorbornadienes and dimethoxynaphthaleno norbornadienes using s-tetrazines or ACE coupling techniques to afford framework structures where different geometrical interrelationships can be attained between the chromophores.

  融合的降冰片烯和含有2,4-二氯嘧啶和2,4-二甲氧基嘧啶单元的三环[4.2.2.1 2,5 ]十一烷基-3,7,9-三烯与降冰片二烯，苯并降冰片二烯和二甲氧基萘二降冰片二烯偶联，使用s-四嗪或ACE偶联技术提供框架结构，其中发色团之间可以实现不同的几何相互关系。
• Ninhydrin as a building block in scaffold-linked chromophoric dyad construction
  作者：Davor Margetic、David A. Mann、Ronald N. Warrener

  DOI：10.3998/ark.5550190.p008.520

  日期：——

  The reaction of ninhydrin with ester-activated cyclobutene epoxide (CE-1) containing the fused 1,4-dimethoxynaphthalene (DMN) chromophore, gave adducts formed by 1,3-dipolar cycloaddition at the central (C-2)-CO (major) and the outer (C-1,C-3)-CO (minor) positions. Conversion of the minor adduct to quinoxalines (QIN) by reaction with o-phenylenediamines at the alpha-dione moiety, albeit in poor yield, led to spiro-DMN-1,4 sigma-QIN dyad in which the plane of the chromophore was orthogonally orientated yet angled to the plane of the DMN chromophore. Reaction of ninhydrin with o-phenylenediamines yielded the corresponding 11-oxoindeno[1,2-b]quinoxalines which were coupled with CE-BLOCKs to form spiro adducts by reaction at the carbonyl site; the product from CE-1 was identical with that formed above. Another class of spiro-fused dyads was produced by reaction of ninhydrin with a primary amine followed by cycloaddition of CE-BLOCKs at the carbonyl site, where the amine was available to deliver one chromophore and the CE-BLOCK another.