9-tricyclo[3.3.1.1^3,7]decane-9H-fluorene | 82817-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-tricyclo[3.3.1.1^3,7]decane-9H-fluorene
• 英文别名: 2-(9H-fluoren-9-ylidene)adamantane；9-(2-Adamantylidene)fluorene
• CAS: 82817-19-4
• 化学式: C₂₃H₂₂
• 分子量: 298.428
• InChiKey: VPRALLHDWVVAPH-UHFFFAOYSA-N

物化性质

• 熔点：
  232-234 °C(Solv: ethanol (64-17-5); acetone (67-64-1))
• 沸点：
  456.3±15.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 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-tricyclo[3.3.1.1^3,7]decane-9H-fluorene 在 氧气 、 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到spiro[2H-adamantyl-2,9'(10'H)-phenanthren-10'-one]
  参考文献：
  名称：

  铝盐诱导的受阻烯烃的电子转移反应。

  摘要：

  通过与铝盐反应，受阻烯烃1-6可以根据反应条件和试剂的特殊特性提供不同的反应产物，例如二氧环乙烷，环氧化物，酮，或均烯丙基，烯丙基和乙烯基卤代衍生物。

  DOI：

  10.1016/s0040-4039(00)71233-0
• 作为产物：
  描述：

  金刚烷-2-硫酮 在 三苯基膦 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 9-tricyclo[3.3.1.1^3,7]decane-9H-fluorene
  参考文献：
  名称：

  Adam, Waldemar; Encarnacion, Luis A. Arias, Chemische Berichte, 1982, vol. 115, # 7, p. 2592 - 2605

  摘要：

  DOI：

文献信息

• 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。
• Aerobic epoxidation of hindered olefins and enol ethers catalyzed by a polymerizable β-ketoesterate complex of iron(III)
  作者：Luigi Lopez、Piero Mastrorilli、Giuseppe Mele、Cosimo F. Nobile

  DOI：10.1016/s0040-4039(00)73259-x

  日期：1994.5

  Peculiar hindered olefins and derivatives have been epoxidized, under Mukaiyama's conditions, using iron(III) catalytic centres. The experimental results allow to rule out the involvement of singlet oxygen and free peroxyacids as active species.

  在Mukaiyama的条件下，已使用铁（III）催化中心将特殊的受阻烯烃和衍生物进行了环氧化。实验结果可以排除单重态氧和游离过氧酸作为活性物质的参与。
• Oxiranes having an acridane structure as a novel chemiluminescent precursor: synthesis and chemiluminescent studies
  作者：Kazuyuki Miyashita、Masatoshi Minagawa、Yohko Ueda、Yukie Tada、Nobuhiro Hoshino、Takeshi Imanishi

  DOI：10.1016/s0040-4020(01)00216-2

  日期：2001.4

  Oxirane derivatives having acridane and adamantane structures were designed as a novel chemiluminescent precursor and were found to have a characteristic chemiluminescent ability which is introduced by a two-step trigger reaction involving treatment with alkaline H2O2 and subsequent acidic treatment. Structural study of the oxirane derivatives showed that the CIEEL mechanism is involved in this chemiluminescent reaction and it was also found that the chemiluminescent profile is affected by the kind of acid employed in the trigger reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 9-Adamantylidene-10-alkyl-9,10-dihydroacridine oxide as a novel and potential chemiluminescent precursor: Proximity effect of the nitrogen atom
  作者：Takeshi Imanishi、Yohko Ueda、Masatoshi Minagawa、Nobuhiro Hoshino、Kazuyuki Miyashita

  DOI：10.1016/s0040-4039(97)00791-0

  日期：1997.6

  An oxirane derivative having acridane and adamantane moieties was prepared and proved to show potential chemiluminescent property on treatment with alkaline hydroperoxide and subsequently with hydrochloric acid, in which the electron-donating property of the nitrogen was experimentally shown to play an important role for the chemiluminescence. (C) 1997 Elsevier Science Ltd.
• Monodeoxygenation of spiro adamantane-1,2-dioxetanes induced by aminium salt
  作者：Luigi Lopez、Gianluca M. Farinola、Angelo Nacci、Stefano Sportelli

  DOI：10.1016/s0040-4020(98)00375-5

  日期：1998.6

  The reactions of 4,4-dimethylspiro[adamantane-2,3'-[ 1,2]-diaxetane] (1a) and biadamantylidene-1, 2-dioxetane (2a) in dichloromethane, at different reaction temperatures, with tris(2,4-dibromophenyl) aminium hexachloroantimonate A afford high yields of the rearranged ketones 2-methyladamantyl-methyl ketone (3) and spiro[adamantane-2,4'-homoadamantan-5'-one] (8), respectively. A cation radical monodeoxygenation process is suggested. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.