2-(4-甲氧基苯基)-1H-茚 | 54288-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 中文名称: 2-(4-甲氧基苯基)-1H-茚
• 英文名称: 2-(4-methoxyphenyl)-1H-indene
• CAS: 54288-29-8
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: JBZBIBVSVDZKAA-UHFFFAOYSA-N

物化性质

• 沸点：
  335.1±21.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基苯基)-1H-茚 在 氢溴酸 、 溶剂黄146 作用下， 反应 24.0h， 以15%的产率得到2-(4-Hydroxyphenyl)indene
  参考文献：
  名称：

  Regioselectivity and stereoselectivity in the photodimerization of rigid and semirigid stilbenes

  摘要：

  The (2-pi + 2-pi)-photodimerizations of 2-phenylindene (1), 2-(4-methoxyphenyl)indene (9), and 5,10-dihydroindeno[2,1-a]indene (2) were investigated in a variety of homogeneous and micellar solvents. Four isomeric photodimers were formed from 1 and 9: syn-head-to-tail, syn-head-to-head, anti-head-to-tail, and anti-head-to-head. Relative yields of these as well as syn/anti- and head-to-tail (ht)/head-to-head (hh) ratios were determined in various solvents and as a function of temperature. In 1 syn/anti ratios ranged from 1.07 to 1.62 and ht/hh ratios from 0.88 to 1.28. In 9 syn/anti ratios between 0.83 and 2.55 and ht/hh ratios between 0.4 and 1.2 were found; preferred formation of anti and hh products was observed in micellar solvents as expected from preorientation of reactants. Two photodimers (ht and hh) were found upon irradiation of 2. ht/hh ratios ranged from 0.89 to 1.56. The variations of these ratios can be understood on the basis of a kinetic scheme, in which individual excimer states as precursors of the respective dimers are involved.

  DOI：

  10.1021/jo00041a035
• 作为产物：
  描述：

  4-甲氧基苯乙烯 在 lithium aluminium tetrahydride 、 niobium pentachloride 、 sodium acetate 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(4-甲氧基苯基)-1H-茚
  参考文献：
  名称：

  Low-valent Niobium-mediated Synthesis of Indenes: Intramolecular Coupling Reaction of CF₃Group with Alkene C–H Bond

  摘要：

  CF3取代的o-烯烃-α,α,α-三氟甲苯在NbCl5/LiAlH4体系下与烯烃C–H键发生了分子内偶联反应。获得了产率良好的取代茚类化合物。

  DOI：

  10.1246/cl.2007.24

文献信息

• Selective arylation at the vinylic site of cyclic olefins
  作者：Xiaojin Wu、Jianrong (Steve) Zhou

  DOI：10.1039/c3cc41722k

  日期：——

  Cyclic olefins usually give Heck products having an aryl ring residing at the allylic or homoallylic position. We describe herein a new method that allows arylation at the vinylic position of various cyclic olefins.

  环烯烃通常得到具有在烯丙基或均烯丙基位置上的芳基环的Heck产物。我们在本文中描述了一种新的方法，该方法允许在各种环状烯烃的乙烯基位置进行芳基化。
• Architectural Stabilization of a Gold(III) Catalyst in Metal-Organic Frameworks
  作者：John S. Lee、Eugene A. Kapustin、Xiaokun Pei、Sebastián Llopis、Omar M. Yaghi、F. Dean Toste

  DOI：10.1016/j.chempr.2019.10.022

  日期：2020.1

  decomposition pathways are challenging to address in transition-metal catalysis and have previously not been suppressed via incorporation into a solid support. Two robust metal-organic frameworks (IRMOF-10 and bio-MOF-100) are used for the architectural stabilization of a structurally well-defined gold(III) catalyst. The inherent rigidity of these materials is utilized to preclude a unimolecular decomposition

  单分子分解途径在过渡金属催化中难以解决，并且以前没有通过掺入固体载体中而被抑制。两个坚固的金属有机骨架（IRMOF-10和bio-MOF-100）用于结构明确的金（III）催化剂的结构稳定化。这些材料的固有刚度可用于排除单分子分解途径-还原消除。通过这种体系结构稳定化策略，未观察到金属有机骨架中结合的金（III）催化剂的分解。相反，均质类似物易于在溶液中分解。在这些金属-有机骨架中稳定催化剂可防止浸出并实现可回收性，这对于生产性多相催化至关重要。
• Gold for the Generation and Control of Fluxional Barbaralyl Cations
  作者：Paul R. McGonigal、Claudia de León、Yahui Wang、Anna Homs、César R. Solorio-Alvarado、Antonio M. Echavarren

  DOI：10.1002/anie.201207682

  日期：2012.12.21

  comparison with the shape‐shifting barbaralyl cation, which exists as a mixture of 181 400 degenerate forms. Gold‐catalyzed cycloisomerizations of 7‐alkynyl cyclohepta‐1,3,5‐trienes were found to proceed via fluxional barbaralyl intermediates (see scheme). The evolution of the intermediates into 1‐ or 2‐substituted indenes could be controlled by the choice of gold complex.

  与具有两种身份的青蛙王子相比，异形的野蛮人阳离子以181400个简并形式的混合物形式存在，因此显得苍白。发现金催化的7-炔基环庚-1,3,5-三烯的环异构化是通过助熔的barbaralyl中间体进行的（参见方案）。可以通过选择金络合物来控制中间体向1或2取代的茚基的演化。
• Nickel-catalyzed Carboannulation Reaction of <i>o</i>-Bromobenzyl Zinc Bromide with Unsaturated Compounds
  作者：Ruixue Deng、Liangdong Sun、Zhi Li

  DOI：10.1021/ol702167t

  日期：2007.12.1

  A number of indenes have been prepared in good yields by treating o-bromobenzyl zinc bromide 1 with various terminal and internal alkynes in the presence of a nickel catalyst. The nickel-catalyzed carboannulation reaction was successfully extended to the synthesis of indane derivatives by reaction of 1 with acrylates and styrene.

  在镍催化剂的存在下，通过用各种末端和内部炔烃处理邻溴苄基溴化锌1，已经以高收率制备了许多茚。通过1与丙烯酸酯和苯乙烯的反应，镍催化的碳环化反应成功地扩展到了茚满衍生物的合成。
• Supported palladium nanoparticle‐catalysed Suzuki–Miyaura cross‐coupling approach for synthesis of aminoarylbenzosuberene analogues from natural precursor
  作者：Richa Bharti、C. Bal Reddy、Sandeep Kumar、Pralay Das

  DOI：10.1002/aoc.3749

  日期：2017.11

  semi‐synthetic method has been developed for the synthesis of aminoarylbenzosuberenes (AABs) from naturally occurring himachalenes, an isomeric mixture of sesquiterpenes present in Cedrus deodara oil. Polymer‐stabilized Pd(0) nanoparticle‐catalysed Suzuki–Miyaura cross‐coupling reaction of aminovinyl bromide‐substituted benzosuberenes has been adopted for AAB synthesis. The catalyst performed well with different

  已开发出一种半合成方法，用于从天然存在的喜马ale烯（一种存在于雪松杜达拉油中的倍半萜的异构体混合物）合成氨基芳基苯并sub烯（AAB）。聚合物稳定的Pd（0）纳米颗粒催化的氨基乙烯基溴取代的苯并sub烯的Suzuki-Miyaura交叉偶联反应已用于AAB合成。该催化剂在不同的胺取代基上表现良好，并循环使用五次。通过半合成方法从天然前体合成此类芳基化的苯并亚戊烯类化合物可提供一种有吸引力的替代方法，减少步骤数。