4,5-dibromobenzo-18-crown-6 | 108695-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-dibromobenzo-18-crown-6
• 英文别名: 18,19-Dibromo-2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecine；20,21-dibromo-2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(22),18,20-triene
• CAS: 108695-55-2
• 化学式: C₁₆H₂₂Br₂O₆
• mdl: MFCD00382533
• 分子量: 470.155
• InChiKey: LMBHRNOMDYJMDL-UHFFFAOYSA-N

物化性质

• 熔点：
  65-68 °C
• 沸点：
  528.6±50.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dibromobenzo-18-crown-6 在 吡啶 、 喹啉 、 盐酸 、 氨 、 lithium 、 锌 作用下， 反应 8.0h， 生成 2,3,5,6,8,9,11,12,14,15-Decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecine-18,19-dithiol
  参考文献：
  名称：

  Lowe, Nigel D.; Garner, C. David, Journal of the Chemical Society, Dalton Transactions, 1993, p. 2197 - 2208

  摘要：

  DOI：
• 作为产物：
  描述：

  苯并-18-冠-6-醚 在 溴 、 碘 、 铁粉 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以53%的产率得到4,5-dibromobenzo-18-crown-6
  参考文献：
  名称：

  含酞菁和冠醚亚基的宿主的合成及聚集行为

  摘要：

  描述了四种新的有机主体，它们包含一个酞菁核，四个冠醚环连接到该核上。这些主体包括具有 18-crown-6 环的游离碱酞菁和具有 15-crown-5、18-crown-6 和 21-crown-7 环的三种铜酞菁。大环化合物是由苯并冠醚分三步合成的。在溶液中，酞菁倾向于形成聚集体。这种聚集受溶剂极性和碱金属盐存在的影响，这些盐与冠部配位。直径与冠醚环直径相匹配的阳离子与新宿主形成 4:4 的主客体复合物。当阳离子的直径超过冠醚环的直径时，形成主客体化学计量比为 8:4 的配合物。提出了铜酞菁主体的结合自由能，并与苯并冠醚的结合自由能进行了比较。结合图谱支持 UV-vis 实验的结果；即，大阳离子引起大环的聚集。自 20 年前佩德森发现冠醚 1 以来，已经发表了数百篇关于这些化合物化学的论文。 2 关于酞菁和相关大环的论文数量甚至更多。 3 直到最近，还没有任何论文已经发表了描述包含两种类型环系统的宿主。

  DOI：

  10.1021/ja00248a021

文献信息

• Auto-Tandem Catalysis: Synthesis of Acridines by Pd-Catalyzed C=C Bond Formation and C(<i>sp²</i>)-N Cross-Coupling
  作者：Zhongxing Huang、Yang Yang、Qing Xiao、Yan Zhang、Jianbo Wang

  DOI：10.1002/ejoc.201201070

  日期：2012.10.10

  A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C–N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized

  通过连续的C=C双键形成和C-N交叉偶联实现了钯催化合成吖啶的简便方法。各种功能化的吖啶可以通过简单的操作从容易获得的邻二卤代苯和 N-甲苯磺酰腙中获得。这种一锅法在两个耦合伙伴方面具有广泛的范围，并为功能化吖啶衍生物提供了一种有效的途径，这些衍生物通常难以通过以前已知的方法合成。
• Synthesis of Functionalized Benzo-18-Crown-6 Compounds via the Suzuki-Miyaura Cross-Coupling Reaction
  作者：Sambasivarao Kotha、Dhurke Kashinath

  DOI：10.1055/s-2005-861840

  日期：——

  Various functionalized 4'-and 4',5'-benzo-18-crown-6 compounds have been synthesized using the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction as a key step. Treatment of the bromobenzocrowns with various arylboronic acids in presence of palladium-catalyst and aqueous Na 2 CO 3 gave the biphenyl-based benzocrowns in good yields.

  以钯催化的 Suzuki-Miyaura 交叉偶联反应为关键步骤，合成了各种功能化的 4'-和 4',5'-benzo-18-crown-6 化合物。在钯催化剂和Na 2 CO 3 水溶液的存在下，用各种芳基硼酸处理溴苯并冠以良好的收率得到基于联苯的苯并冠。
• Trofimova; Gorbunova; Tolkacheva, Russian Journal of Coordination Chemistry, 1999, vol. 25, # 6, p. 402 - 407
  作者：Trofimova、Gorbunova、Tolkacheva、Tsivadze

  DOI：——

  日期：——
• Photochemical Charge Separation in Supramolecular Phthalocyanine−Multifullerene Conjugates Assembled by Crown Ether-Alkyl Ammonium Cation Interactions
  作者：Francis D’Souza、Eranda Maligaspe、Atula S. D. Sandanayaka、Navaneetha K. Subbaiyan、Paul A. Karr、Taku Hasobe、Osamu Ito

  DOI：10.1021/jp1028195

  日期：2010.10.21

  Self-assembled phthalocyanine multifullerene donor acceptor conjugates have been formed by crown ether-ammonium cation dipole-ion binding strategy to probe the photochemical charge separation. To achieve this, phthalocyanine is functionalized to possess four 18-crown-6 moieties on the macrocycle periphery, whereas fullerene is functionalized to possess an alkyl ammonium cation of short and long chain lengths. Stable donor acceptor conjugates accommodating multifullerene entities have been obtained by the crown ether-ammonium cation inclusion complexation. From the efficient fluorescence quenching of the zinc phthalocyanine by the bound fullerene entities, the rate constants of charge separation are evaluated to be slightly larger for closely held via shorter alkyl chain length fullerene, which are also larger compared to the earlier reported analogous zinc porphyrin multifullerene conjugate. Nanosecond transient absorption studies yielded spectral signatures corresponding to both the phthalocyanine radical cation and fullerene radical anion at the same time, providing evidence of light-induced electron transfer within the conjugates. The evaluated lifetimes of the radical ion pairs in the present phthalocyanine fullerene conjugates are found to be hundreds of nanoseconds and are much longer compared to the earlier reported conjugate of zinc porphyrin analogue, revealing higher possible usage of the generated radical ion pairs.
• Novel alanyl-amino peptidase inhibitors for functionally influencing different cells and treating immunological, inflammatory, neuronal, and other diseases
  申请人：Ansorge Siegfried

  公开号：US20070037752A1

  公开（公告）日：2007-02-15

  The invention relates to substances which specifically inhibit peptidases splitting ala-p-nitroanilide for use in medicine. The invention further relates to the use of at least one such substance or of a pharmaceutical or cosmetic composition containing at least one such substance for the prophylaxis and therapy of diseases, in particular the prophylaxis and therapy of diseases with an overshooting immune response (autoimmune diseases, allergies and transplant rejections), of other chronic inflammatory diseases, neuronal diseases and brain damages, skin diseases (acne and psoriasis, among others), tumor diseases and special virus infections (including SARS).