(E)-9-(3-phenylallylidene)-9H-fluorene | 32174-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (E)-9-(3-phenylallylidene)-9H-fluorene
• 英文别名: 9-Cinnamylidene fluorene；9-[(E)-3-phenylprop-2-enylidene]fluorene
• CAS: 32174-26-8
• 化学式: C₂₂H₁₆
• 分子量: 280.369
• InChiKey: FDELSKWIDIUQDN-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-bromo-3-phenylprop-2-yne 在 1,1'-双(二苯基膦)二茂铁 、 正丁基锂 、 palladium diacetate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 18.0h， 生成 (E)-9-(3-phenylallylidene)-9H-fluorene
  参考文献：
  名称：

  通过金 (I) 或三氯化镓催化的炔烃的加氢芳基化合成荧蒽。

  摘要：

  亲电金 (I) 催化剂 6 与 GaCl(3) 竞争作为通过炔烃分子内加氢芳基化合成荧蒽的首选催化剂。这种催化剂用于制备聚芳烃的潜力通过在一锅转化中合成两个官能化十环烯来说明，其中三个 CC 键高效地形成。

  DOI：

  10.3762/bjoc.7.178

文献信息

• Catalytic amide base system generated <i>in situ</i> for 1,3-diene formation from allylbenzenes and carbonyls
  作者：Masanori Shigeno、Akihisa Kajima、Kunihito Nakaji、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1039/d0ob02007a

  日期：——

  The amide base generated in situ from tetramethylammonium fluoride and N(TMS)3 catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound. The system is applicable to the transformations of a variety of allylbenzenes with functional groups (halogen, methyl, phenyl, methoxy, dimethylamino, ester, and amide moieties). Acyclic and cyclic diaryl ketones, pivalophenone, pivalaldehyde

  由氟化四甲基铵和N（TMS）3原位生成的酰胺基催化从烯丙基苯和羰基化合物的合成1,3-二烯。该系统适用于各种具有官能团（卤素，甲基，苯基，甲氧基，二甲基氨基，酯和酰胺部分）的烯丙基苯的转化。无环和环状二芳基酮，新戊苯酮，新戊醛和异丁酮苯用作偶联伙伴。还阐明了反式β-甲基对苯二酚在产物形成中的作用。
• Synthesis of 9-Fluorenylidenes via Pd-Catalyzed C–H Vinylation with Vinyl Bromides
  作者：Shuai Yang、Yanghui Zhang

  DOI：10.1021/acs.orglett.1c02722

  日期：2021.10.15

  A facile and efficient approach for the synthesis of 9-fluorenylidenes has been developed via the palladium-catalyzed cross-coupling of 2-iodobiphenyls and vinyl bromides. The reaction involves the C–H activation of 2-iodobiphenyls and dual C–C bond formations. A range of 9-fluorenylidene derivatives, including diphenyldibenzofulvenes, can be synthesized with the reaction.

  通过钯催化的 2-碘联苯和乙烯基溴的交叉偶联，开发了一种简便有效的合成 9-芴基的方法。该反应涉及 2-碘联苯的 C-H 活化和双 C-C 键的形成。通过该反应可以合成一系列 9-芴基衍生物，包括二苯基二苯并富烯。
• Palladium-catalyzed coupling reaction of 2-iodobiphenyls with alkenyl bromides for the construction of 9-(diorganomethylidene)fluorenes
  作者：Ya-Heng Zhao、Jian-Long Wang、Yun-Bing Zhou、Miao-Chang Liu、Hua-Yue Wu

  DOI：10.1039/d1ob01547h

  日期：——

  protocol for the construction of 9-(diorganomethylidene)fluorenes through palladium-catalyzed coupling reactions of 2-iodobiphenyls with alkenyl bromides has been reported. The reaction proceeds through the C–H activation/oxidative addition/reduction elimination/intramolecular Heck coupling reaction to afford a series of 9-(diorganomethylidene)fluorenes with good yields. Control experiments demonstrate that

  已经报道了通过钯催化的 2-碘联苯与烯基溴的偶联反应构建 9-（二有机亚甲基）芴的原子经济协议。该反应通过C-H活化/氧化加成/还原消除/分子内Heck偶联反应进行，以良好的收率得到一系列9-(二有机亚甲基)芴。对照实验表明，五元钯环作为关键中间体，β-H 消除作为限速步骤。
• α-Bromoacrylic Acids as C1 Insertion Units for Palladium-Catalyzed Decarboxylative Synthesis of Diverse Dibenzofulvenes
  作者：Minghao Zhang、Wenbo Deng、Mingjie Sun、Liwei Zhou、Guobo Deng、Yun Liang、Yuan Yang

  DOI：10.1021/acs.orglett.1c01888

  日期：2021.8.6

  Herein α-bromoacrylic acids have been employed as C1 insertion units to achieve the palladium-catalyzed [4 + 1] annulation of 2-iodobiphenyls, which provides an efficient platform for the construction of diverse dibenzofulvenes. This protocol enables the formation of double C(aryl)–C(vinyl) bonds via a C(vinyl)–Br bond cleavage and decarboxylation. It is particularly noteworthy that the method features

  在本文中，α-溴丙烯酸已被用作 C1 插入单元以实现钯催化的 2-碘联苯的 [4+1] 环化，这为构建各种二苯并富烯提供了一个有效的平台。该协议能够通过 C(乙烯基)-Br 键裂解和脱羧形成双 C(芳基)-C(乙烯基)键。特别值得注意的是，该方法具有广泛的底物范围，并且可以成功地将各种有趣的框架，如桥环、稠（杂）芳环和二乙烯基苯结合到产品中。
• Environmental Actinide Science
  作者：Robert J. Silva、Heino Nitsche

  DOI：10.1557/mrs2001.181

  日期：2001.9

  Considerable progress has been made in the study of environmental plutonium science in the last 30-plus years, driven to a large extent by concerns about the release and migration of large amounts of plutonium into the accessible geosphere. Plutonium has been introduced into the environment through several pathways. Environmental contamination has been caused by nuclear-weapons production and testing, nuclear-reactor accidents, and accidents during the transport of nuclear weapons. Above-ground testing of more than 420 nuclear weapons has produced large amounts of radionuclides through fission and neutron activation products. More than three metric tons of plutonium have been distributed on the earth's surface by global fallout. For example, the MAYAK plutonium production complex in the former Soviet Union is located in the southern Urals, about 70 km north of Chelyabinsk and 15 km east of Kyshtym. Between 1949 and 1951, about 76 million m3 of liquid radioactive waste with a total activity of 100 PBq (2.7 MCi) were discharged into the Techa River.

  在过去30多年里，在环境钚科学研究方面取得了相当大的进展，这在很大程度上是由于对大量钚释放和迁移进入可接近的地球圈的担忧驱动的。钚是通过几种途径引入环境的。核武器生产和测试、核反应堆事故以及核武器运输事故导致了环境污染。超过420枚核武器的地面试验产生了大量的放射性核素，包括裂变和中子激活产物。全球超过3吨的钚通过全球性沉降分布在地球表面。例如，前苏联的MAYAK钚生产基地位于乌拉尔山脉南部，距切尔雅宾斯克市北约70公里，东约15公里处的克什蒂姆。1949年至1951年间，约7600万立方米的液体放射性废物，总活度为100 PBq（2.7 MCi），被排放到特恰河中。

表征谱图