1,4,7,10,13,20,23,26,29,32-decaoxa<13.13>m-cyclophane-16,35-dicarbonyl chloride | 131110-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4,7,10,13,20,23,26,29,32-decaoxa<13.13>m-cyclophane-16,35-dicarbonyl chloride
• 英文别名: bis<5-(chlorocarbonyl)-1,3-phenylene>-32-crown-10；2,5,8,11,14,20,23,26,29,32-Decaoxatricyclo[31.3.1.115,19]octatriaconta-1(37),15(38),16,18,33,35-hexaene-17,35-dicarbonyl chloride
• CAS: 131110-55-9
• 化学式: C₃₀H₃₈Cl₂O₁₂
• 分子量: 661.531
• InChiKey: BTXTYFSIKCJJBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  44
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,4,7,10,13,20,23,26,29,32-decaoxa<13.13>m-cyclophane-16,35-dicarbonyl chloride 、 α,α-5,15-bis(2'-aminophenyl)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyrin 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以61.5%的产率得到
  参考文献：
  名称：

  Gunter, Maxwell J.; Johnston, Martin R., Journal of the Chemical Society. Perkin transactions I, 1994, # 8, p. 995 - 1008

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 palladium on activated charcoal sodium hydroxide 、 氯化亚砜 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 60.0h， 生成 1,4,7,10,13,20,23,26,29,32-decaoxa<13.13>m-cyclophane-16,35-dicarbonyl chloride
  参考文献：
  名称：

  Gunter, Maxwell J.; Johnston, Martin R., Journal of the Chemical Society. Perkin transactions I, 1994, # 8, p. 995 - 1008

  摘要：

  DOI：

文献信息

• Acid/base-controllable fluorescent molecular switches based on cryptands and basic N-heteroaromatics
  作者：Ming Cheng、Jing Zhang、Xintong Ren、Shuwen Guo、Tangxin Xiao、Xiao-Yu Hu、Juli Jiang、Leyong Wang

  DOI：10.1039/c7cc07469g

  日期：——

  Two kinds of fluorescent BMP32C10-based cryptands 1 and 2 have been developed. Cryptand 1 contains a binaphthol group, while cryptand 2 bears a coumarin group in their third arms. Based on this design, novel self-assemblies constructed from cryptand 1 or 2 and basic N-heteroaromatic guests 3–6 were successfully obtained. Moreover, the threading/dethreading processes of the host–guest complexes could

  已经开发了两种基于荧光BMP32C10的配体1和2。穴状配体1包含一个Binaphthol基团，而穴状配体2在其第三臂中带有一个香豆素基团。基于此设计，成功获得了由配体1或2和基本的N-杂芳族客体3–6构成的新型自组装体。此外，通过交替添加酸/碱，并伴随荧光的同时变化，可以很好地切换宿主-客体复合物的穿线/脱线过程。
• A pillar[5]arene-fused cryptand: from orthogonal self-assembly to supramolecular polymer
  作者：Qi Wang、Ming Cheng、Yue Zhao、Lin Wu、Juli Jiang、Leyong Wang、Yi Pan

  DOI：10.1039/c5cc00130g

  日期：——

  A supramolecular polymer based on a novel pillar[5]arene-fused cryptand host was successfully constructed by the orthogonal self-assembly of two host–guest interactions.

  基于一种新颖的pillar[5]arene融合的cryptand主体，通过两种宿主-客体相互作用的正交自组装成功构建了一种超分子聚合物。
• A porphyrin-based crown ether co-receptor for the complexation of paraquat
  作者：Maxwell J. Gunter、Martin R. Johnston

  DOI：10.1016/s0040-4039(00)97738-4

  日期：1990.1
• “Reverse” pyridyl cryptands as hosts for viologens
  作者：Adam M.‐P. Pederson、Terry L. Price、Daniel V. Schoonover、Carla Slebodnick、Harry W. Gibson

  DOI：10.1002/hc.21422

  日期：2018.5

  AbstractTwo new cryptands, 2 and 4, were prepared from bis(m‐phenylene)‐32‐crown‐10 (BMP32) 5,5'‐diacid chloride and dibenzo‐30‐crown‐10 (DB30) 4,4'‐diacid chloride, respectively, by reaction with pyridine‐2,6‐dimethanol. The resultant cryptands 2 and 4 have the ester moieties reversed from the previously reported isomers, 1 and 3. These “reverse” cryptands display lower association constants with viologen derivatives than the original cryptands; this is rationalized by the conjugation of the ester moieties with the aromatic rings, which reduces their electron‐donating properties and offsets the increased basicity of the pyridyl nitrogen atoms. The crystal structure of the BMP32‐based cryptand 2 indeed confirms the coplanarity of the ester and aromatic moieties and indicates that, as a result, the available cavity is quite small and that the pyridyl nitrogen atom points away from the cavity.
• Synthesis and Properties of Cholesteryl Esters Bearing 32- and 16-Membered Crown Ethers
  作者：Devdatt S. Nagvekar、Yadollah Delaviz、Abaneshwar Prasad、Joseph S. Merola、Herve Marand、Harry W. Gibson

  DOI：10.1021/jo950097l

  日期：1996.1.1

  The cholesteryl esters (3b and 3a) of 5-carboxy-1,3-phenylene-16-crown-5 and 5-carboxy-4,6-dichloro-1,3-phenylene-16-crown-5 show cholesteric liquid crystalline behavior but only upon heating samples that were rapidly cooled from the isotropic melt in the case of 3a and a monotropic phase for 3b. The dichloro compound 3a was formed by treatment of the corresponding acid 2 with SOCl2 first and then cholesterol; it is believed that the SOCl2 was contaminated with SO2Cl2, leading to the chlorination of the aromatic ring. The dichloro compound 3a was structurally characterized using single crystal X-ray diffraction. 3a crystallizes in the orthorhombic space group P2(1)2(1)2(1) With unit cell parameters of a = 12.76(4) Angstrom, b = 17.511(5) Angstrom, and c = 18.213 Angstrom. Use of freshly opened SOCl2 produced 3b. The reaction of the acid 2 and cholesterol in the presence of dicyclohexylcarbodiimide yielded the acylisourea 4 as the major product (64%) along with 3b (36%) upon treatment with cholesterol. The dicholesteryl ester 9 of bis(5-carboxy-1,3-phenylene)-32-crown-10 (8a) was also synthesized, and by differential scanning calorimetry (DSC) and polarized optical microscopy no liquid crystalline behavior was observed with this system. Apparently the presence of the semirigid crown in the molecule prevents the two cholesteryl moieties from organizing in independent helices. The complexation ability of this cholesteryl crown (9) with methyl viologen bis(hexafluorophosphate) ([paraquat]. 2[PF6]) (12) in acetone has been examined by H-1 NMR spectroscopy; it showed weaker binding than its simple dimethyl ester analog 8b.