9-异丙基蒽 | 1498-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9-异丙基蒽
• 中文别名: 蒽,9-(1-甲基乙基)-
• 英文名称: 9-isopropylanthracene
• 英文别名: 9-propan-2-ylanthracene
• CAS: 1498-80-2
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: LQRJPEHNMOASNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  153-160 °C(Press: 1.3 Torr)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  9-异丙基蒽 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 3.0h， 以57%的产率得到bromo-9 isopropyl-10 anthracene
  参考文献：
  名称：

  Aromatic amine compound, organic electroluminescent element including the same, and display device including organic electroluminescent element

  摘要：

  一种芳香胺化合物由通式[I]表示：其中X1和X2分别代表从烷基，芳基，烯丙基，烷氧基和芳氧基中选择的基团，X1和X2可以相同也可以不同，Ar1和Ar2分别代表芳基，n≧1，取代基Y中至少有一个取代基选自三氟甲基基团，氰基和卤素基团，其他取代基Y是分别选自氢基，烷基，芳基，烯丙基，烷氧基和芳氧基的基团。

  公开号：

  US08357821B2
• 作为产物：
  描述：

  9-isopropylidene-9,10-dihydro-anthracene 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 9-异丙基蒽
  参考文献：
  名称：

  9-Isopropylidene-9,10-dihydroanthracene. Synthesis, stereochemistry, and the effect of 10-alkyl group size on the equilibrium with 9-isopropyl-10-alkylanthracene

  摘要：

  DOI：

  10.1021/ja00838a030

文献信息

• Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents
  作者：Carlos Vila、Massimo Giannerini、Valentín Hornillos、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1039/c3sc53047g

  日期：——

  Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C–C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

  钯催化的二级C(sp3)有机金属试剂交叉偶联反应一直是有机合成中的一个长期挑战，主要由于与不期望的异构化或还原产物形成相关的问题。基于我们最近开发的与有机锂试剂的催化C–C键形成反应，本文呈现了一种钯催化的二级烷基锂试剂与芳基和烯基溴化物的交叉偶联反应。该反应在室温下进行，反应时间短，选择性和产率均很高。这一方法也适用于受阻的芳基溴化物，而这在金属催化的交叉偶联反应中是一个主要挑战。
• Reactions of cupric halides with organic compounds—III
  作者：D. Mosnaim、D.C. Nonhebel、J.A. Russell

  DOI：10.1016/s0040-4020(01)82883-0

  日期：1969.1

  9-Alkyl and 9-arylanthracenes have been shown to undergo halogenation with cupric halides to give good yields of their 10-halogenated derivatives. Electron-donating groups in 9-arylanthracenes were shown to increase the rate of reaction. The results are interpreted in terms of a ligand-transfer mechanism.

  已显示9-烷基和9-芳基蒽通过卤化铜进行卤化以使其10-卤代衍生物具有良好的产率。显示9-芳基蒽中的给电子基团可增加反应速率。结果是根据配体转移机理来解释的。
• Efficient Synthesis of Sterically Hindered Arenes Bearing Acyclic Secondary Alkyl Groups by Suzuki-Miyaura Cross-Couplings
  作者：Chengxi Li、Tianyu Chen、Bowen Li、Guolan Xiao、Wenjun Tang

  DOI：10.1002/anie.201411518

  日期：2015.3.16

  Bulky P,PO ligands were designed to inhibit isomerization and reduction side reactions during the cross coupling between sterically hindered aryl halides and alkylboronic acids. Suzuki–Miyaura cross‐couplings between di‐ortho‐substituted aryl bromides and acyclic secondary alkylboronic acids have been achieved with high yields. The method has also enabled the preparation of ortho‐alkoxy di‐ortho‐substituted

  庞大的P，P = O配体设计用于在位阻芳基卤化物和烷基硼酸之间的交叉偶联过程中抑制异构化和还原副反应。高产率地实现了二邻位取代的芳基溴化物和无环仲烷基硼酸之间的Suzuki-Miyaura交叉偶联。该方法还能够以优异的收率制备带有异丙基的邻烷氧基双邻取代芳烃。合成方法的实用性已在雌酮的后期修饰中以及在向棉酚的新合成途径中的应用中得到了证明。
• Restricted Rotation Involving the Tetrahedral Carbon. IL. Singly<i>peri</i>-Substituted 9-Isopropyltriptycenes Revisited
  作者：Gaku Yamamoto、Michinori Oki

  DOI：10.1246/bcsj.56.2082

  日期：1983.7

  9-Isopropyltriptycene derivatives carrying a fluoro, chloro, bromo, or t-butyl substituent in a peri-position were synthesized and their dynamic NMR behavior was studied to see the dependence of the barrier to rotation of the bridgehead substituent upon the bulkiness of the peri-substituent. The data obtained in this work together with those reported earlier disclose that, among the derivatives in which the peri-substituent is not buttressed by the 2-substituent, the peri-methoxy compound has the highest barrier and the barrier decreases as the bulkiness of the peri-substituent increases. 1,2,3,4-Tetrachloro and tetrabromo derivatives show the slightly positive buttressing effect.

  合成了在peri位上携带氟、氯、溴或叔丁基取代基的9-异丙基三苯并衍生物，并研究了它们的动态NMR行为，以观察桥头取代基的旋转障碍与peri取代基的体积之间的关系。此研究获得的数据与早期报道的数据结合显示，在未被2-取代基支撑的peri取代基衍生物中，peri-甲氧基化合物具有最高的旋转障碍，而当peri取代基的体积增大时，旋转障碍减小。1,2,3,4-四氯和四溴衍生物表现出略微正的支撑效应。
• Tele-substitutions en serie anthracenique—II
  作者：J. Rigaudy、A.M. Seuleiman、Nguyen Kim Cuong

  DOI：10.1016/0040-4020(82)80051-3

  日期：1982.1

  A competition between normal substitution and tele-substitution is observed with 9-bromoanthracenes bearing in the opposite meso position an ethyl, 1b, or a benzyl group 1d. When treated with potassium phenoxide in HMPT these bromides afford mixtures of 9-alkyl-10-phenoxy-anthracenes 2 and 9-(α(phenoxyalkyl) anthracenes 3. On the other hand 9-bromo-10 isopropylanthracene 1c is quite unreactive and

  观察到正常取代和遥取代之间的竞争，其中9-溴蒽在相反的内消旋位置带有乙基，1b或苄基1d。当在HMPT中用苯氧钾处理时，这些溴化物可提供9-烷基-10-苯氧基蒽2和9-（α（苯氧基烷基）蒽3的混合物。另一方面，9-溴10异丙基蒽1c几乎没有反应性，而9-溴10异丙基蒽1c则没有反应。溴-d10-甲氧基甲基蒽1e基本上导致了蒽7。