5,11,17,23,29,35-hexa-tert-butyl-37,38,40,41-tetrahydroxy-39,42-(m-xylylenedioxy)calix<6>arene | 154388-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23,29,35-hexa-tert-butyl-37,38,40,41-tetrahydroxy-39,42-(m-xylylenedioxy)calix<6>arene
• 英文别名: 5,11,17,23,29,35-hexa-t-butyl-37,40-[1,3-phenylenebis(methyleneoxy)]-calix[6]arene-38,39,41,42-tetrol；5,11,17,23,29,35-Hexatert-butyl-38,46-dioxanonacyclo[17.17.11.13,7.19,13.121,25.127,31.140,44.015,47.033,37]dopentaconta-1(36),3,5,7(52),9(51),10,12,15,17,19(47),21,23,25(50),27(49),28,30,33(37),34,40(48),41,43-henicosaene-49,50,51,52-tetrol
• CAS: 154388-69-9
• 化学式: C₇₄H₉₀O₆
• 分子量: 1075.53
• InChiKey: HUOGIJJQGKHCEE-UHFFFAOYSA-N

物化性质

• 密度：
  1.090±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  21.1
• 重原子数：
  80
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,11,17,23,29,35-hexa-tert-butyl-37,38,40,41-tetrahydroxy-39,42-(m-xylylenedioxy)calix<6>arene 以87%的产率得到
  参考文献：
  名称：

  Otsuka Hideyuki, Araki Koji, Shinkai Seiji, J. Org. Chem, 59 (1994) N 6, S 1542-1547

  摘要：

  DOI：
• 作为产物：
  描述：

  4-叔丁基杯[6]芳烃 、 间二溴苄 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 5,11,17,23,29,35-hexa-tert-butyl-37,38,40,41-tetrahydroxy-39,42-(m-xylylenedioxy)calix<6>arene
  参考文献：
  名称：

  Metal-induced conformational changes in calix[n]arenes can change the exchange interaction between N–O· radicals

  摘要：

  合成了两种稳定的N–O·自由基位于下边缘的Calix[n]芳酯2n（n=4和6）：在26中，交换相互作用（El）会因金属诱导的1,2,3交替到圆锥构象的变化而改变，但在24中，金属诱导的羰基旋转不足以改变El。

  DOI：

  10.1039/c39950002121

文献信息

• Structural Elucidation of 1,3-Phenylenebis(methylene)-Bridged Calix[6]arenes with Four Uncapped Hydroxy Groups
  作者：Toshiyuki Saiki、Shigehisa Akine、Kei Goto、Norihiro Tokitoh、Takayuki Kawashima、Renji Okazaki

  DOI：10.1246/bcsj.73.1893

  日期：2000.8

  )-bridged calix[6]arenes with four uncapped hydroxy groups at the lower rim and various kinds of functionalities on the bridging unit were synthesized. Their structures in solution and in the crystalline state were determined by NMR spectroscopy, molecular mechanics calculations, and X-ray crystallographic analyses. They were found to adopt a pinched cone conformation, where the bridging 1,3-phenylenebis(methylene)

  合成了 1,3-亚苯基双(亚甲基)-桥连杯[6]芳烃，其下缘有四个未封端的羟基，桥接单元上有各种官能团。它们在溶液中和结晶状态下的结构通过核磁共振光谱、分子力学计算和 X 射线晶体学分析确定。发现它们采用收缩锥体构象，其中桥接的 1,3-亚苯基双（亚甲基）单元位于下方，从而形成锥体的底部。这些分子中有很强的分子内氢键网络，形成环状阵列；该网络被认为在稳定收缩锥体构象方面发挥着重要作用。还研究了桥接单元的构象迁移率。
• Conformational Control of Calix[6]arenes Through Multiple Bridges
  作者：Hitos Galán、Javier de Mendoza、Pilar Prados

  DOI：10.1002/ejoc.200500368

  日期：2005.10

  synthesis of the A,D-m-xylylene-bridged B,C,E,F-tetra-O-alkylcalix[6]arenes 1b–c and the A,D-B,C;E,F-triply bridged calix[6]arenes 2a–c is described. The cone conformation of the new bridged calix[6]arenes has been established by a full set of 1D/2D 1H and 13C NMR techniques. These compounds are substantially more rigid than calix[6]arene analogues with an A,D-p-xylylene bridge, and the resulting cavities

  A,Dm-亚二甲苯基桥连B,C,E,F-四-O-烷基杯[6]芳烃1b-c和A,DB,C;E,F-三重桥连杯[6]芳烃的合成描述了 2a-c。新型桥接杯[6]芳烃的锥体构象已通过全套1D/2D 1H和13C NMR技术建立。这些化合物比具有 A,Dp-亚二甲苯基桥的杯 [6] 芳烃类似物的刚性要高得多，并且产生的空腔更清晰。三重桥接杯[6]芳烃2b和2c的分子力学优化导致结构与核磁共振谱完全一致。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Conformational Mobility of the Bridged Calix[6]arenes with Allyl and Ethyl Groups at the Lower Rim
  作者：Shigehisa Akine、Kei Goto、Takayuki Kawashima

  DOI：10.1246/bcsj.74.2167

  日期：2001.11

  The conformational mobility of the bridged calix[6]arenes with allyl and ethyl groups at the lower rim was investigated. Allylation of the tetrahydroxy compounds afforded two isomers: 5a (cone) and 5b (1,2,3-alternate), which were separated by silica-gel chromatography. These isomers underwent slow isomerization at room temperature with a half-life time of about 2 weeks. On the other hand, the ethyl

  研究了在下缘具有烯丙基和乙基的桥连杯[6]芳烃的构象迁移率。四羟基化合物的烯丙基化得到两种异构体：5a（锥体）和 5b（1,2,3-替代物），它们通过硅胶色谱法分离。这些异构体在室温下缓慢异构化，半衰期约为 2 周。另一方面，发现乙基衍生物 6-9 以构象异构体的混合物形式存在于溶液中；它们是在 NMR 时间尺度上独立观察到的，但在实验室时间尺度上是不可分割的。6-9 的两种异构体的比例取决于桥接单元的官能度，其影响通过分子力学计算进行研究。在结晶状态下，发现具有溴官能团的乙基衍生物 6 具有 1,2,
• Syntheses of All Possible O-Methylation Products Derivable from 5,11,17,23,29,35-Hexa-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol
  作者：Hideyuki Otsuka、Koji Araki、Seiji Shinkai

  DOI：10.1021/jo00085a048

  日期：1994.3

  We here report methods for the synthesis of all twelve possible 0-methylation products from 5,11,17,23,29,35-hexa-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol (1): one mono-, three di-, three tri-, three tetra-, one penta-, and one hexamethylated products. The strategies used are (i) direct O-methylation with different 1/K2CO3 ratios, (ii) selective mono-O-methylation of O-alkylation products, (iii) demethylation with TiCl4 or LiI, and (iv) protection-deprotection with a benzyl group or an o- or m-xylenyl group. We believe that these O-methylation products are useful as basic skeletons to design functionalized calix[6]arenes with the desired number of substituents and regioselectively-positioned functional groups.
• Isolation and structural analysis of novel conformational isomers of the m-xylylene-bridged calix[6]arenes: the ‘partial cone’ and ‘inverted cone’ isomers
  作者：Shigehisa Akine、Kei Goto、Takayuki Kawashima

  DOI：10.1016/s0040-4039(02)02833-2

  日期：2003.2

  In the benzylation of a m-xylylene-bridged calix[6]arene tetrol, the first example of the 'partial cone' isomer of a calix[6]arene was obtained in addition to the corresponding cone and 1,2,3-alternate isomers, and its structure was established by X-ray crystallographic analysis. The synthesis and crystal structure of the 'inverted cone' isomer as well as its thermal conversion to the 'normal cone' isomer are also described. (C) 2003 Elsevier Science Ltd. All rights reserved.