5,6-diiodoacenaphthene | 55143-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,6-diiodoacenaphthene
• 英文别名: 5,6-Dijodacenaphthen；5,6-diiodo-1,2-dihydroacenaphthylene
• CAS: 55143-88-9
• 化学式: C₁₂H₈I₂
• 分子量: 406.005
• InChiKey: YBDKFSOJSZIVFK-UHFFFAOYSA-N

物化性质

• 熔点：
  159-160 °C
• 沸点：
  415.1±45.0 °C(Predicted)
• 密度：
  2.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,6-diiodoacenaphthene 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 (6-phenylstibinoacenaphth-5-yl)-mesityltellurenyl triflate
  参考文献：
  名称：

  Intramolecularly Group 15 Stabilized Aryltellurenyl Halides and Triflates

  摘要：

  The preparation of a series of functionalized pen-substituted acenaphthyl compounds 6-Ph2E-Ace-5-Br (1, E = As; 2, E = Sb), 6-Ph2As-Ace-5-TeMes (3), 5-I-Ace6-TeMes (4), 6-Ph2Sb-Ace-5-TeMes (5), (6-Ph2P-Ace-5)(2)Te (6), [6-R2E-Ace-5-Te]X (7, E = P, R = Ph, X = Cl; 8, E = P, R = i-Pr, X = Cl; 9, E = P, R = i-Pr, X = Br; 10, E = P, R = i-Pr, X = I; 11, E = P, R = i-Pr, X = 1/2 (TeI6); 12, E = P, R = i-Pr, X = 13; 13, E = P, R = Ph, X = O3SCF3; 14, E = As, R = Ph, X = O3SCF3; 15, E = Sb, R = Ph, X = 03SCF3), and [6-PhSbAce-5-TeMes]O3SCF3 (16) is reported (Ace = acenaphthyl). The synthesis of 7-15 was achieved either by a salt metathesis reaction of 5-i-Pr2P-Ace-6-Li with TeCl2 center dot TMTU (8), TeBr2 center dot TMTU (9), and Tell. (10 + 11) or by the aryl cleavage reaction of 6-R2E-Ace-5-TeMes (E = P, As, Sb; R = Ph, i-Pr) with HgCl2 (7), I-2 (12), and HO3SCF3 (13-15). The reaction of 5 with triflic acid gave also rise to the formation of [6-PhSb-Ace-5-TeMes] O3SCF3 (16). All compounds have been characterized by multinuclear NMR spectroscopy and single-crystal X-ray diffraction. Complementary DFT studies including relaxed potential energy scans (PES) and subsequent topological analysis of the resulting electron and pair densities according to the AIM and ELI-D partitioning schemes were performed for the aryltellurenyl chlorides [6-Ph2P-Ace-S-Te]Cl, [8-Me2N-Nap-1-Te]Cl, and [8-Me2P-Nap-1-Te]Cl in the gas phase and in MeCN solution, whereby the Te-Cl distances were systematically varied. The same analyses were carried out for the fully optimized [6-R2E-Ace-5-Te](+) cations (E = P, As, Sb) and compared to those of the previously studied intermolecularly stabilized [R(3)ETeMes](+) cations (E = P, As, Sb).

  DOI：

  10.1021/acs.organomet.5b00813
• 作为产物：
  描述：

  5,6-dilithioacenaphthene-N,N,N',N'-tetramethyl-1,2-ethanediamine 在 碘 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 生成 5,6-diiodoacenaphthene
  参考文献：
  名称：

  5,6-Dilithioacenaphthene-N,N,N',N'-Tetramethyl-1,2-乙二胺配合物与α-二酮的反应。I.cis-Directing 1:1 环状加成与无环和环状 α-二酮及相关化合物

  摘要：

  在 -10–0 °C 下，5,6-二溴苊与丁基锂和二胺在乙醚中很容易生成标题络合物 (3)。3与联乙酰反应得到顺式1,2,5,6-四氢-1,2-二甲基...

  DOI：

  10.1246/bcsj.54.3020

文献信息

• An Experimental Acidity Scale for Intramolecularly Stabilized Silyl Lewis Acids
  作者：Sandra Künzler、Saskia Rathjen、Anastasia Merk、Marc Schmidtmann、Thomas Müller

  DOI：10.1002/chem.201903241

  日期：2019.11.27

  shifts and the 1 J(CF) coupling constants of these nitrilium ions vary in a predictable manner with the donor capability of the stabilizing group. The spectroscopic parameters are suitable probes for scaling the acidity of Lewis acids. These new probes allow for the discrimination between very similar Lewis acids, which is not possible with conventional NMR tests, such as the well-established Gutmann-Beckett

  提出了一种新的基于NMR的路易斯酸度标度，并证明了其在甲硅烷基路易斯酸中的应用。对氟苯甲腈（FBN）与甲硅烷基阳离子的反应可通过与远端硫属基或卤素供体相互作用而在内部稳定，从而在三角双锥体配位环境中与硅原子产生甲硅烷基化的腈离子。这些腈离子的19 F NMR化学位移和1 J（CF）耦合常数随稳定基团的供体能力以可预测的方式变化。光谱参数是用于调节路易斯酸的酸度的合适探针。这些新的探针可以区分非常相似的路易斯酸，这在常规NMR测试（如公认的Gutmann-Beckett方法）中是不可能的。
• Onset of three-centre, four-electron bonding in peri-substituted acenaphthenes: A structural and computational investigation
  作者：Lara K. Aschenbach、Fergus R. Knight、Rebecca A. M. Randall、David B. Cordes、Alex Baggott、Michael Bühl、Alexandra M. Z. Slawin、J. Derek Woollins

  DOI：10.1039/c1dt11697e

  日期：——

  observed previously for the analogous naphthalene compounds N1–N12 (Nap[X][EPh], Nap[EPh][E′Ph] (X = Br, I; E/E′ = S, Se, Te). The conformation of the aromatic ring systems and subsequent location of p-type lone-pairs dominates the geometry of the peri-region. The differences in peri-separations observed for compounds adopting differing conformations of the peri-substituted phenyl group can be correlated

  已经制备了两个系列的空间拥挤的周边取代的ena啶，它们在A1-A6（Acenap [X] [EPh]（Acenap = ena-5,6-diyl; X = Br，I； E = S，Se，Te）和A7–A12中的硫族硫属元素（Acenap [EPh] [E'Ph]（Acenap = ena-5,6-二基； E / E'= S， （Se，Te）。还制备了相关的二卤化物A13-A16 Acenap [XX']（XX'= BrBr，II，IBr，ClCl）。相互作用的卤素和硫族元素原子的空间体积占据周围位置。ena系列经历在普遍增加围为分子容纳较重的同源-separation并映射趋势先前为类似萘观察化合物N1-N12（NAP [X] [EPH，NAP [EPH] [E'Ph]（X = Br的，I; E / E'= S，硒，碲）的芳族环系及p型孤对后续位置的构象支配的几何形状围-region中的差
• Bridging the Gap: Attractive 3c–4e Interactions in <i>peri</i> ‐Substituted Acenaphthylenes
  作者：Louise M. Diamond、Fergus R. Knight、Kasun S. Athukorala Arachchige、Rebecca A. M. Randall、Michael Bühl、Alexandra M. Z. Slawin、J. Derek Woollins

  DOI：10.1002/ejic.201301549

  日期：2014.3

  dehydrogenation of the ethane backbone. The related dihalide compounds 13 and 14 Acenapyl[XX] (XX = BrBr, II) have also been prepared by following a similar procedure, and 1,2,5,6-tetrabromo-1,2-dihydroacenaphthylene A0 was prepared as an intermediate by following an alternative route to 13. The series of acenaphthylene compounds have remarkably similar molecular structures to their acenaphthene counterparts;

  一系列周围取代的苊，在 1-6 [苊基 [X](EPh) 的 5,6-位含有混合卤素 - 硫属元素官能团（苊基 = 苊-5,6-二基；X = Br，I； E = S, Se, Te)] 和 7-11 [Acenap(EPh)(EPh) (Acenap = acenaphthene-5,6-diyl; E/E = S, Se, Te)] 中的硫族元素-硫属元素部分通过利用 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 对乙烷骨架进行脱氢，从其相应的苊类似物 A1-A11 制备。相关的二卤化物化合物 13 和 14 Acenapyl[XX] (XX = BrBr, II) 也已按照类似程序制备，并制备了 1,2,5,6-四溴-1,2-二氢苊A0 作为中间体沿着另一条路线前往 13。该系列苊化合物的分子结构与其对应的苊化合物非常相似；随着较重的同系物占据接近的周边位置，它们表现出预期的
• Intramolecular Halo Stabilization of Silyl Cations—Silylated Halonium‐ and Bis‐Halo‐Substituted Siliconium Borates
  作者：Anastasia Merk、Lukas Bührmann、Natalie Kordts、Katharina Görtemaker、Marc Schmidtmann、Thomas Müller

  DOI：10.1002/chem.202004838

  日期：2021.2.15

  The stabilizing neighboring effect of halo substituents on silyl cations was tested for a series of peri‐halo substituted acenaphthyl‐based silyl cations 3. The chloro‐ (3 b), bromo‐ (3 c), and iodo‐ (3 d) stabilized cations were synthesized by the Corey protocol. Structural and NMR spectroscopic investigations for cations 3 b–d supported by the results of density functional calculations, which indicate

  对甲硅烷基的阳离子卤素取代基的稳定邻近的效果进行了一系列的测试周围卤代取代的苊基甲硅烷基阳离子3。氯（3 b），溴（3 c）和碘（3 d）稳定的阳离子是根据Corey规程合成的。密度泛函计算结果支持了阳离子3 b - d的结构和NMR光谱研究，表明它们的ha离子性质。根据氟苯甲腈（FBN）方法，甲硅烷基路易斯酸度沿一系列的离子3，氟离子3a降低是非常强的碘离子3d是中等的路易斯酸 卤离子3b和3c在取代基再分布反应中与起始硅烷反应并形成硅离子4b和4c。硼酸硅4c 2 [B 12 Br 12 ]的结构揭示了在顶端位置具有两个溴取代基的硅原子的三角双锥体配位环境。
• Synthesis of Paracyclo(1,8)napthalenophane and Paracyclo(5,6)acenaphthenophane
  作者：Akira Kasahara、Taeko Izumi、Iwao Shimizu、Masahiro Satou、Takao Katou

  DOI：10.1246/bcsj.55.2434

  日期：1982.8

  [2]Paracyclo[2]paracyclo[2](1,8)naphthalenophan-9-ene-1,17-diyne, [0]paracyclo[2]paracyclo[0](5,6)acenaphthenophan-7-ene, and [2]paracyclo[2]paracyclo[2](5,6)acenaphthenophan-9-ene-1,17-diyne, were synthesized by intramolecular reductive coupling reaction of the corresponding carbonyl compounds with low-valent titanium reagent. The structures of the compounds were elucidated by NMR analyses, and the transannular π-electronic interactions between two benzene rings were examined on the basis of electronic spectra.

  通过分子内还原偶联反应与低价钛试剂合成了[2]对并环[2]对并环[2](1,8)萘-9-烯-1,17-二炔、[0]对并环[2]对并环[0](5,6)苊-7-烯和[2]对并环[2]对并环[2](5、6)苊-9-烯-1,17-二炔是通过相应羰基化合物与低价钛试剂的分子内还原偶联反应合成的。通过核磁共振分析阐明了这些化合物的结构，并根据电子能谱研究了两个苯环之间的跨annular π-电子相互作用。