(+/-)-2,7,12-Tris(2-hydroxyethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene | 162060-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-2,7,12-Tris(2-hydroxyethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene
• 英文别名: 2-[[12,19-Bis(2-hydroxyethoxy)-6,13,20-trimethoxy-5-tetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaenyl]oxy]ethanol
• CAS: 162060-76-6
• 化学式: C₃₀H₃₆O₉
• 分子量: 540.61
• InChiKey: LRJMHZLDHXXQNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+/-)-2,7,12-Tris(2-hydroxyethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 在 sodium hydroxide 、 sodium iodide 、 锌 作用下， 以 吡啶 、 六甲基磷酰三胺 、 乙二醇二甲醚 、 甲酸 、 溶剂黄146 为溶剂， 反应 24.5h， 生成 cryptophane-A
  参考文献：
  名称：

  通过（C 3）-亚基的立体定向复制合成（D 3）-双（环三藜芦基）巨笼

  摘要：

  （D 3）-双（环三藜芦基）（4），是通过（C 3）-亚基的立体特异性复制以外消旋和旋光形式合成的；（+）-（4）的绝对构型是由（C 3）前体的绝对构型分配的。

  DOI：

  10.1039/c39810001137
• 作为产物：
  描述：

  (+/-)-2,7,12-Tris(methoxycarbonylmethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-2,7,12-Tris(2-hydroxyethoxy)-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene
  参考文献：
  名称：

  通过（C 3）-亚基的立体定向复制合成（D 3）-双（环三藜芦基）巨笼

  摘要：

  （D 3）-双（环三藜芦基）（4），是通过（C 3）-亚基的立体特异性复制以外消旋和旋光形式合成的；（+）-（4）的绝对构型是由（C 3）前体的绝对构型分配的。

  DOI：

  10.1039/c39810001137

文献信息

• Synthesis of C3-cyclotriveratrylene ligands for iron(II) and iron(III) coordination
  作者：Gilles Vériot、Jean-Pierre Dutasta、Galina Matouzenko、André Collet

  DOI：10.1016/0040-4020(94)00904-9

  日期：1995.1

  The design and synthesis of a new family of siderophores based on cyclotriveratrylene is described. The ligands consist of a C3-cyclotriveratrylene unit provided with three arms (spacers) ending with hydroxamate, catecholate, bipyridine, or iminopyridine units suitable for the octahedral coordination of transition metals and particularly for the complexation of iron(II) and iron(III).

  描述和设计了基于环三藜芦烯的新型铁载体家族。配体由一个C3-环三碳杂戊二烯单元和三个臂（间隔基）组成，它们的末端为异羟肟酸酯，邻苯二酚，联吡啶或亚氨基吡啶单元，适用于过渡金属的八面体配位，特别是铁（II）和铁（III）的络合。
• Regioselective one-step synthesis of trans-3,trans-3,trans-3 and e,e,e [60]fullerene tris-adducts directed by a C3-symmetrical cyclotriveratrylene tether
  作者：Gwénaël Rapenne、François Diederich、Jeanne Crassous、André Collet、Luis Echegoyen

  DOI：10.1039/a903226f

  日期：——

  The first covalent cyclotriveratrylene (CTV)–C60 adducts were prepared by the tether-directed Bingel reaction, which gave the two C3-symmetrical trans-3,trans-3,trans-3 and e,e,e tris-adducts with a high degree of regioselectivity.

  第一个共价环戊三烯（CTV）-C60加合物是通过链式定向宾格尔反应制备的，该反应产生了两个具有高度区域选择性的C3对称反式-3,反式-3,反式-3和e,e,e三加合物。
• Regioselectivity in Tether-Directed Remote Functionalization - The Addition of a Cyclotriveratrylene-Based Trimalonate to C60 Revisited
  作者：Agnieszka Kraszewska、Pablo Rivera-Fuentes、Gwénaël Rapenne、Jeanne Crassous、Ana G. Petrovic、José Lorenzo Alonso-Gómez、Elisa Huerta、François Diederich、Carlo Thilgen

  DOI：10.1002/ejoc.201000396

  日期：——

  The Bingel addition of a trimalonate derived from a chiral, cyclotriveratrylene (CTV)-based tripodal tether to C60 was reinvestigated. The present use of enantiomerically pure (P)and (M)-configured CTV units in the tether allowed the isolation of a total of four enantiomerically pure C3-symmetric trisadducts of [60]fullerene (two from each CTV enantiomer). With the support of NMR and UV/Vis spectroscopy

  重新研究了衍生自手性、基于环三戊四烯 (CTV) 的三脚架系链的三丙二酸酯与 C60 的宾格尔加成。目前在系链中使用对映体纯的 (P) 和 (M) 配置的 CTV 单元允许分离 [60] 富勒烯的总共四个对映体纯 C3 对称三加合物（每个 CTV 对映体中的两个）。在 NMR 和 UV/Vis 光谱、电子 (ECD) 和振动 (VCD) 圆二色光谱分析的支持下（与已知化合物的 ECD 数据以及通过 TD-DFT 或
• Selective Binding and Easy Separation of C70 by Nanoscale Self-Assembled Capsules
  作者：Elisa Huerta、Gerald A. Metselaar、Alex Fragoso、Eva Santos、Carles Bo、Javier de Mendoza

  DOI：10.1002/anie.200603223

  日期：2007.1
• ——
  作者：Gwénaël Rapenne、Jeanne Crassous、Lourdes E. Echegoyen、Luis Echegoyen、Erica Flapan、François Diederich

  DOI：10.1002/1522-2675(20000607)83:6<1209::aid-hlca1209>3.0.co;2-y

  日期：2000.6.7

  The C-3-symmetrical [60]fullerene-cyclotriveratrylene (CTV) tris-adducts (+/-)-1 (with a trans-3,trans-3,trans-3 addition pattern) and (+/-)-2 (with an e,e,e addition pattern) were prepared in 11 and 9% yield, respectively, by the regio- and diastereoselective tether-directed Bingel reaction of C-60 with the tris-malonate-appended CTV derivative (+/-)-3 (Scheme). This is the first example for tris-adduct formation by a one-step tether-directed Bingel addition. Interchromophoric interactions between the electron-rich CTV cap and the electron-attracting fullerene moiety have a profound effect on the electrochemical behavior of the C-sphere (Fig. 4 and Table 1). The fullerene-centered first reduction potentials in compounds (+/-)-1 and (+/-)-2 are by 100 mV more negative than those of their corresponding tris[bis(ethoxycarbonyl)methano][60]fullerene analogs that lack the CTV cap. A particular interest in (+/-)-1 and (+/-)-2 arises from the topological chirality of these molecules. A complete topology study is presented, leading to the conclusion that the four possible classical stereoisomers of the e,e,e regioisomer are topologically different, and, therefore, there exist four different topological stereoisomers (Fig. 6). Interestingly, in the case of the trans-3,trans-3,trans-3 tris-adduct, there are four classical stereoisomers but only two topological stereoisomers (Fig. 7). An example of a target molecule representing a topological meso-form is also presented (Fig. 8).