(+/-)-2,7,12-triiodo-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene | 168566-60-7

• 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-triiodo-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene
• 英文别名: 5,12,19-Triiodo-6,13,20-trimethoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene
• CAS: 168566-60-7
• 化学式: C₂₄H₂₁I₃O₃
• 分子量: 738.142
• InChiKey: FMTKAMUNHZMNJX-UHFFFAOYSA-N

物化性质

• 沸点：
  648.8±55.0 °C(Predicted)
• 密度：
  1.905±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2,7,12-triiodo-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  有机铂桥环三亚苄基二聚体

  摘要：

  包含一个炔基和两个腈官能团的不对称环三亚苄基（CTB）与顺式- [PtL 2 Cl 2 ]（L=PEt 3或L 2 =1,3-双（二苯基膦）丙烷）反应，得到Pt桥联的CTB二聚体。当使用 CuI 作为合成辅助剂时，还分离出了 (Pt, Cu) 双核配合物，其中 CuCl/CuI 部分与铂结合的双炔基钳 π 配位。然而，单核CTB二聚体与[ML 2 ] 2+的1:2反应没有生成金属隐烷。

  DOI：

  10.1002/ejic.202300284
• 作为产物：
  描述：

  (+/-)-2,7,12-triamino-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene 在 盐酸 、 potassium iodide 、 sodium nitrite 作用下， 生成 (+/-)-2,7,12-triiodo-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzocyclononene
  参考文献：
  名称：

  Garcia, Chantal; Collet, Andre, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 52 - 58

  摘要：

  DOI：

文献信息

• Generation of Cryptophanes in Water by Disulfide Bridge Formation
  作者：Frédérique Brégier、Oldřích Hudeček、Fanny Chaux、Marie-José Penouilh、Jean-Claude Chambron、Pavel Lhoták、Emmanuel Aubert、Enrique Espinosa

  DOI：10.1002/ejoc.201700537

  日期：2017.7.17

  cyclotribenzylene (CTB) subunits. The formation of cryptophanes in basic aqueous solutions (0.1 m MOD; M = Li, Na, K, and Cs) by disulfide bridge formation has been investigated. Two original CTBs, 1H6 and 2H6, derived from cyclotriphenolene through the introduction of mercaptomethyl and mercapto substituents, respectively, were synthesized. Cryptophane formation by slow oxygenation of 16– was observed

  Cryptophanes 是由两个桥接凹形环苯并亚基 (CTB) 亚基组成的受体。已经研究了通过二硫键形成在碱性水溶液（0.1 m MOD；M = Li、Na、K 和 Cs）中形成隐甲。通过引入巯基甲基和巯基取代基分别从环三苯酚衍生出两种原始 CTB，1H6 和 2H6。仅在 Me4N+ 作为模板存在的情况下观察到通过 16- 缓慢氧化形成的隐甲，其产生的非对映体形式的比例约为 82:18。相比之下，刚性 CTB 2H6 在没有模板的情况下立体选择性地产生了隐甲。有趣的是，在 0 中存在 Me4N+（0.5-1 当量/16-）的情况下，16- 和 26- 的 1:1 混合物的空气氧化。1 m LiOD 导致隐甲复合物 [(1·1)6–⊃+NMe4] 的独家形成，(2·2)6– 仅以非常少的量形成。在反应混合物中没有检测到混合物质。在 ωB97XD 6-311G(d,p) 理论水平下，通过 DFT
• Edge-Directed Dynamic Covalent Synthesis of a Chiral Nanocube
  作者：Di Xu、Ralf Warmuth

  DOI：10.1021/ja800803c

  日期：2008.6.18

  The dynamic multicomponent syntheses of nanometer-sized chiral molecular cubes 1a and 1b from 8 tritopic 90 degrees corner units and 12 linear spacers using an edge-directed approach is described. Thus, the TFA-catalyzed reaction of 8 equiv C3- trihexadecycloxy-triformylcyclotribenzylene 2 as corner unit with 12 equiv of 1,4-phenylenediamine 3a or benzidine 3b as spacers yields nanocubes 1a and 1b, respectively in close to quantitative yield. The same reactions carried out with enantiomerically pure (P)-2(> 99% ee) gave the homochiral cubes (all-P)-1a and (all-P)-1b. Force field calculations predict an edge length of 17 angstrom and 21 angstrom for 1a and 1b, which is consistent with their dimensions estimated from DOSY experiments. Furthermore, the asymmetric syntheses of (P)-2 through dynamic thermodynamic resolution is described. This approach is based on the TFA-catalyzed reaction of racemic 2 with (R,R)-1,2-diaminocyclohexane (R)-5, which leads to a chiral cryptophane (> 90% yield) that is built-up from two (P)-2 linked together with three diamines (R)-5. Hydrolysis of this cryptophane provides (P)-2 with > 99% ee.
• Development of Functionalized Cyclotriveratrylene Analogues: Introduction of Withdrawing and π-Conjugated Groups
  作者：Lisa Peyrard、Marie-Laurence Dumartin、Sabine Chierici、Sandra Pinet、Gediminas Jonusauskas、Pierre Meyrand、Isabelle Gosse

  DOI：10.1021/jo301183b

  日期：2012.8.17

  Cyclotriveratrylene analogues (CTVs) are supramolecular bowl-shaped molecules known for their ability to complex organic and organometallic guests, to form liquid crystals, polymers, or nanostructures. In this Article, we report the synthesis of new cyclotriveratrylene analogues with fluorescence properties in which various electron-withdrawing or pi-extended conjugated groups are appended to the wide rim ortho to the methoxy-donating groups. Synthetically, these functionalized CTVs cannot be obtained as CTVs with electron-rich functions by the typical method (i.e., the trimerization of the corresponding benzyl alcohol) but are prepared from a common key intermediate, the C-3-triiodocyclotriveratrylene (CTV-I-3), in good yields. Despite the synthetic difficulties encountered due to the presence of three reactive centers, we have demonstrated the possibility of performing Sonogashira coupling and Huisgen cycloaddition reactions directly to the CTV core for the first time. CTVs with pi-extended conjugated groups reveal interesting fluorescence profiles. More broadly, this study utilizes CTV-I-3 to introduce novel functionalities into CTVs to keep exploring their potential applications.