dibenzobarallene | 103515-22-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: dibenzobarallene
• 英文别名: cis-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid anhydride；9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride；17-Oxapentacyclo[6.6.5.0(2,7).0(9,14).0(15,19)]-nonadeca-2,4,6,9,11,13-hexaene-16,18-dione；17-oxapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
• CAS: 103515-22-6
• 化学式: C₁₈H₁₂O₃
• mdl: MFCD00152427
• 分子量: 276.291
• InChiKey: PSKVQQJLLWSBFV-UHFFFAOYSA-N

物化性质

• 熔点：
  258-259 °C
• 沸点：
  492.7±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dibenzobarallene 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以91%的产率得到2,3-(9,10-dihydro-9,10-anthracenediyl)-γ-butylactone
  参考文献：
  名称：

  通过蒽Diels–Alder序列合成取代的3-呋喃-2（5 H）-ones

  摘要：

  蒽和顺丁烯二酸酐的Diels-Alder加合物衍生的内酯进行去质子化然后进行亲电淬灭，可得到高产率的α-取代内酯。特别值得注意的是与氯代三甲基硅烷的反应，仅得到C-甲硅烷基化的产物。烷基化产物的快速真空热解（FVP）以良好的总产率提供了3-取代的呋喃-2（5 H）-一。

  DOI：

  10.1016/j.tetlet.2006.04.097
• 作为产物：
  描述：

  11-氰基-9,10-二氢-9,10-乙基蒽-11-羧酸 在 4-二甲氨基吡啶 、 四磷十氧化物 、 对苯二酚 、 N,N'-二环己基碳二亚胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 dibenzobarallene
  参考文献：
  名称：

  Fluorescent Cyanoacrylate Monomers and Polymers for Fingermark Development

  摘要：

  Cyanoacrylate esters with fluorescent side groups were synthesized and tested as agents for latent fingerprint development. Reactive monomers with benzyl, anthracyl, naphthyl, fluorenyl, propagyl, and cyanomethyl side groups were synthesized using the formation of an ethyl cyanoacrylate, anthracene adduct, followed by hydrolysis of the ethyl ester to the acid and esterification with a desired alcohol, and finally release of the monomer by retro-Diels-Alder with maleic anhydride. Monomers were prepared in high yield and purity as determined by spectral analysis. Attempts to synthesize these monomers from poly(ethyl cyanoacrylate) by transesterification and depolymerization resulted in low yields and low purity. The synthesized fluorescent monomers were found to be effective for latent fingerprint development in solution forming clear fluorescent fingerprint images suitable for forensic fingerprint comparison. These monomers can complement the current use of the commonly used nonfluorescent ethyl cyanoacrylate monomers for fingerprint development.

  DOI：

  10.1021/ma400837h

文献信息

• Synthesis, Anti-inflammatory and Analgesic Evaluation of Certain New 3a,4,9,9a-Tetrahydro-4,9-benzenobenz[f]isoindole-1,3-diones
  作者：A. A. Abu-Hashem、M. A. Gouda

  DOI：10.1002/ardp.201100020

  日期：2011.8

  analgesic and anti‐inflammatory activities, we reported here the synthesis and in‐vivo analgesic and anti‐inflammatory evaluation of various series of 2‐substituted‐3a,4,9,9a‐tetrahydro‐4,9‐benzeno‐benz[f]isoindole‐1,3‐diones: [4‐Bromobutoxy] 6, 5‐bromopentoxy 7, [4‐(4‐phenylpiperazin‐1‐yl)butoxy] 9, [5‐(4‐phenylpiperazin‐1‐yl)pentoxy] 10, 2‐(2(4)‐(4‐phenylpiperazin‐1‐yl)‐2‐oxoethyl/4‐oxobutyl 17, 19, [

  为了建立具有改善的镇痛和抗炎活性的新候选物，我们在此报告了各种系列的 2-取代 - 3a、4、9、9a-四氢 - 4 的合成和体内镇痛和抗炎评估, 9 - benzeno - benz [f]isoindole - 1,3- diones: [4 - bromobutoxy] 6, 5 - bromopentoxy 7, [4- (4- phenylpiperazin - 1 - yl) butoxy] 9, [5- (4) -Phenylpiperazin-1-yl) pentoxy] 10, 2- (2 (4) - (4-phenylpiperazin-1-yl) -2-oxoethyl / 4-oxobutyl 17, 19, [2 (4) - (4-methylpiperazine) -1-基] -2-氧乙基/4-氧丁基20、22、[2(4)-吗啉代-2-氧乙基/4-氧丁基]23、25和2(4)-(哌啶-1-基)
• Improving the Affinity and Selectivity of a Nonpeptide Series of Cholecystokinin-B/Gastrin Receptor Antagonists Based on the Dibenzobicyclo[2.2.2]octane Skeleton
  作者：S. Barret Kalindjian、Ildiko M. Buck、Julia R. Cushnir、David J. Dunstone、Martin L. Hudson、Caroline M. R. Low、Iain M. McDonald、Michael J. Pether、Katherine I. M. Steel、Matthew J. Tozer

  DOI：10.1021/jm00021a019

  日期：1995.10

  described a novel series of nonpeptidic cholecystokinin-B (CCKB)/gastrin receptor antagonists based on a dibenzobicyclo[2.2.2]octane skeleton. We wish now to report on compounds arising out of our earlier work which have substantially greater affinity as antagonists for the CCKB/gastrin receptor system and which maintain, or improve on, the already high selectivity with respect to CCKA receptors. Thus

  我们最近描述了基于二苯并双环[2.2.2]辛烷骨架的一系列新的非肽胆囊收缩素-B（CCKB）/胃泌素受体拮抗剂。现在，我们希望报告由我们早期工作产生的化合物，这些化合物作为CCKB /胃泌素受体系统的拮抗剂具有更大的亲和力，并且相对于CCKA受体，该化合物保持或改善了已经很高的选择性。因此，顺式-7-[[[（（1S）-[[3,5-二羧基-苯基）氨基]羰基] -2-苯基乙基]氨基]羰基] -8-[[（1-金刚烷基甲基）氨基]-羰基] -2,3：5,6-二苯并双环[2.2.2]辛烷在CCKB /胃泌素受体的小鼠皮膜中表达的pKi为8.80。这些受体相对于CCKA受体的选择性约为1000倍。
• Fluorous Dienophiles Are Powerful Diene Scavengers in Diels−Alder Reactions
  作者：Stefan Werner、Dennis P. Curran

  DOI：10.1021/ol035214a

  日期：2003.9.1

  [reaction: see text] Three fluorous dienophiles have been synthesized, and their value in scavenging an excess diene after Diels-Alder reactions is shown. The resulting fluorous derivatives are separated by solid-phase extraction on fluorous silica gel (FSPE). The fluorous [1,2,4]triazoline-3,5-dione 10 reacted with most dienes within seconds or minutes.

  [反应：见正文]合成了三种氟二烯亲核体，并显示了它们在Diels-Alder反应后清除过量二烯的价值。通过在氟硅胶（FSPE）上进行固相萃取来分离所得的氟衍生物。氟[1,2,4]三唑啉-3,5-二酮10在数秒或数分钟内与大多数二烯反应。
• Dicarboximide-based clathrate design. Host synthesis, inclusion formation and x-ray crystal structures of a free host and of inclusion compounds with 2- and 3- methylcyclohexanone, 3-methylcyclopentanone, butyronitrile, propan-1-ol and (?)-fenchone guests
  作者：Edwin Weber、Christiane Reutel、Concepci�n Foces-Foces、Antonio L. Llamas-Saiz

  DOI：10.1002/poc.610080306

  日期：1995.3

  Crystalline host compounds consisting of a roof-shaped dicarboxinide framework and pendant diarylethanol analogous subunits were synthesized and shown to form inclusion complexes with small organic molecules such as alcohols, amines, ketones or polar and apolar organic solvents. Clathrate efficiency and selectivity depend on the particular host structure. The crystal and molecular structures of a free

  合成了由屋顶形的二羧甲骨架和侧基二芳基乙醇类似的亚基组成的结晶主体化合物，显示出与小的有机分子（如醇，胺，酮或极性和非极性有机溶剂）形成包合物。包合物的效率和选择性取决于特定的宿主结构。游离主体化合物（2a）和包含化合物[2a·3-甲基环己酮（1：1），1a·3-甲基环戊酮（1：1），1a·2-甲基环己酮（1：1），通过x射线衍射分析确定1b·丁腈（1∶1），1b·丙-1-醇（2∶1）和1b·（-）-甲烯酮（1∶1）]。在所有结构中，羟基均参与分子内氢键，并且主体和客体分子仅通过晶格力保持。残留在主体基质中的通道和空腔足够大，可以允许来宾分子的无序或高热位移参数。所有客人的本地包装系数平均为0·42。
• Molecular docking, modeling, semiempirical calculations studies and in vitro evaluation of new synthesized pyrimidin-imide derivatives
  作者：Ahmed M. Abo-Bakr、Hesham M. Alsoghier、Aboubakr H. Abdelmonsef

  DOI：10.1016/j.molstruc.2021.131548

  日期：2022.2

  with different anhydrides. The synthesized compounds have been investigated and put under several studies suc as, in vitro and in silico techniques, Lipinski's rule of five (RO5), semiempirical (PM6) computational calculations in addition of some physicochemical parameters measurments to evaluate their biological effect against Penicillin-Binding Protein 3 (PBP3) from Escherichia coli. These studies revealed

  通过 4,6-二苯基嘧啶-2-胺1与不同酸酐的缩合反应合成了新的嘧啶-酰亚胺衍生物2-7。已对合成的化合物进行了研究并进行了多项研究，例如体外和计算机技术、Lipinski 的五法则 (RO5)、半经验 (PM6) 计算计算以及一些物理化学参数测量，以评估它们对青霉素的生物效应。来自大肠杆菌的结合蛋白 3 (PBP3) 。这些研究表明，新合成的嘧啶-酰亚胺具有最小的结合能和良好的亲和力，特别是对配体分子5这可能被认为是 PBP3 蛋白的一种有前途的抑制剂。所有新衍生物的结构均通过其元素和光谱分析 IR、1 H NMR、13 C NMR 和 MS得到明确证实。

表征谱图