9,10-dihydro-9,10-ethano-anthracen-11-one | 6372-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dihydro-9,10-ethano-anthracen-11-one
• 英文别名: 9,10-Dihydro-9,10-aethano-anthracen-11-on；9,10-Dihydro-9,10-ethanoanthracen-11-one；tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-one
• CAS: 6372-63-0
• 化学式: C₁₆H₁₂O
• 分子量: 220.271
• InChiKey: FGNVGVBNBOAUFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-9,10-ethano-anthracen-11-one 在 palladium on activated charcoal 氢气 、 硝酸 、 乙酸酐 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Distortion of Olefin and Carbonyl .pi.-Orbitals in Dibenzobicyclo[2.2.2]octatrienes and Dibenzobicyclo[2.2.2]octadienones. Unsymmetrization of .pi. Lobes Arising from .pi.-.pi. Orbital Interactions

  摘要：

  We have detected the unsymmetrical pi faces of the olefin group in 2-substituted dibenzobicyclo-[2.2.2]octatrienes (2-substituted 9,10-dihydro-9,10-ethenoanthracenes) and the carbonyl groups of 2-substituted and 3-substituted dibenzobicycla[2.2.2]octadienones (2-substituted and 3-substituted 9,10-dihydro-9,10-(11-ketoethano)anthracenes), wherein alpha-type overlaps of the pi orbitals are involved, in a similar manner to longicyclic conjugation. An intrinsically nonequivalent substituent at distal positions modulates the epoxidation and dihydroxylation of the olefin group and the reduction of the carbonyl group. Both systems exhibit similar substituent effects: an ''electron-withdrawing'' substituent such as a nitro or fluoro group gave a large to moderate bias (preferred syn attack with respect to the substituent) whereas an ''electron-donating'' methoxy substituent exhibited a negligible bias. Herein we interpret these biases or nonbiases in terms of unsymmetrization of pi lobes of the olefin and carbonyl pi orbitals, arising from nonequivalent pi-pi interactions rather than from an electron-donating or -withdrawing effect.

  DOI：

  10.1021/jo00093a032
• 作为产物：
  描述：

  9,10-二氢-9,10-乙基桥蒽-11-醇 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 9,10-dihydro-9,10-ethano-anthracen-11-one
  参考文献：
  名称：

  THE SYNTHESIS OF 9,10-DIHYDRO-9,10-(11-AMINOETHANO)ANTHRACENES

  摘要：

  DOI：

  10.1021/jo01131a009

文献信息

• Stereoselective Diels–Alder Reactions of <i>gem</i>-Diborylalkenes: Toward the Synthesis of <i>gem-</i>Diboron-Based Polymers
  作者：Nadim Eghbarieh、Nicole Hanania、Alon Zamir、Molhm Nassir、Tamar Stein、Ahmad Masarwa

  DOI：10.1021/jacs.1c01471

  日期：2021.4.28

  to be among the most valuable reagents in modern organic synthesis, providing a rapid access to a wide array of transformations, including the construction of C–C and C-heteroatom bonds, their use as dienophile-reactive groups has been rare. Herein we report the Diels–Alder (DA) reaction of (unsymmetrical) gem-diborylalkenes. These reactions provide a general and efficient method for the stereoselective

  尽管偕二硼基烯烃被认为是现代有机合成中最有价值的试剂之一，可以快速进行各种转化，包括构建 C-C 和 C-杂原子键，但它们作为亲双烯反应基团的用途已经已经很少见了。在此，我们报道了（不对称）宝石二硼基烯烃的狄尔斯-阿尔德（DA）反应。这些反应为偕二硼基烯烃的立体选择性转化以快速获得1,1-双硼基环己烯提供了一种通用且有效的方法。使用与硼化二烯和偕二硼基烯烃相同的 DA 反应歧管，我们还开发了 1,​​1,2-三-和 1,1,3,4-四（硼酸盐）环己烯家族的简洁、高度区域选择性合成方法。目前缺乏有效合成途径的化合物。此外，DFT 计算可以深入了解控制这些 DA 反应的化学选择性、区域选择性和立体选择性的潜在因素。该方法还提供了偕二硼基降冰片烯的立体发散合成。开环复分解聚合（ROMP）证明了偕二硼基降冰片烯结构单元的实用性，为首次合成偕二硼基聚合物提供了高度模块化的方法。此外，这些聚合物已成功
• In search for thioketene S-oxide. A vinyl sulfoxide to sulfine rearrangement
  作者：Nadia Pelloux-Léon、Frédéric Minassian、Jocelyne Levillain、Jean-Louis Ripoll、Yannick Vallée

  DOI：10.1016/s0040-4039(98)00914-9

  日期：1998.7

  Two approaches to thioketene S-oxide have been tested. This reactive heterocumulene was tentatively characterized by low temperature IR spectroscopy. In the course of this study, an unexpected vinyl sulfoxide to sulfine rearrangement was observed.

  已经测试了两种方法制备硫代烯酮S-氧化物。该反应性杂枯烯通过低温红外光谱初步表征。在本研究过程中，观察到意外的乙烯基亚砜到亚砜的重排。
• Synthesis and Effects on Chloroquine Susceptibility in <i>Plasmodium </i><i>f</i><i>alciparum </i>of a Series of New Dihydroanthracene Derivatives
  作者：Sandrine Alibert、Christiane Santelli-Rouvier、Bruno Pradines、Carole Houdoin、Daniel Parzy、Janina Karolak-Wojciechowska、Jacques Barbe

  DOI：10.1021/jm011046l

  日期：2002.7.1

  To suggest a mechanism of action for drugs capable to reverse the chloroquine resistance, a new set of 9,10-dihydro-9,10-ethano and ethenoanthracene derivatives was synthesized and compounds were tested with the aim to assess their effect on chloroquine susceptibility in Plasmodium falciparum resistant strains. With respect to this, reversal of resistance and change in drug accumulation were compared

  为了提出一种能够逆转氯喹耐药性的药物的作用机理，合成了一组新的9,10-二氢-9,10-乙醇和乙炔蒽衍生物，并对其进行了测试，目的是评估其对氯喹敏感性的影响。恶性疟原虫抗性菌株。对此，比较了耐药性的逆转和药物积累的变化。结构-活性关系和分子建模研究使得为逆转剂定义药效基团和提出与某些选定氨基酸相互作用的推定模型成为可能。
• Chiroptical Properties of 10,11-Dihydro-5,10-methano-5<i>H</i>-dibenzo[<i>a</i>,<i>d</i>]cycloheptene Derivatives
  作者：Sanji Hagishita、Kaoru Kuriyama

  DOI：10.1246/bcsj.54.2790

  日期：1981.9

  transitions. Their CD spectra were calculated by the point-dipole exciton treatment and by the π-SCF approximation using the dipole velocity procedure with and without the charge transfer transition between the aromatic chromophores. Thus, the electric transition dipole moment should not be treated as a point dipole at any place and the rotational strength should be calculated by the dipole velocity procedure

  标题化合物由(+)-(9R,10R)-二甲基11-氧代-9,10-二氢-9,10-乙蒽-1,5-二羧酸酯制备。它们的绝对构型由化学反应以及红外和 CD 光谱确定。尽管 2 和 3 (R=NH2) 的 CD 光谱预计会显示出对简单耦合机制的分析的对映模式，但它们在 1Lb 和 1La 苯类跃迁的两个区域中显示出大致相同的正 Cotton 效应量级。它们的 CD 光谱是通过点偶极激子处理和 π-SCF 近似计算的，使用偶极速度程序，有和没有芳香生色团之间的电荷转移跃迁。因此，
• New routes to thioketenes and propadienethione by flash vacuum thermolysis
  作者：Yannick Vallée、Serge Masson、Jean-Louis Ripoll

  DOI：10.1016/s0040-4020(01)90527-7

  日期：1990.1

  The retro-Diels-Alder reaction under flash vacuum thermolysis (FVT) conditions was applied to the synthesis of simple unstabilized thioketenes. Alternatively, these reactive thiocarbonyl compounds were obtained by FVT elimination of methyltrimethylsilyl sulfide from silylated ketene dithioacetals (and for thioketene itself from methyl trimethylsilyl dithioacetate). A synthesis of propadienethione associating

  在快速真空热解（FVT）条件下的逆Diels-Alder反应应用于合成简单的不稳定的硫代乙烯酮。或者，这些反应性硫代羰基化合物可通过FVT从甲硅烷基化的烯酮二硫缩醛中除去甲基三甲基甲硅烷基硫化物而获得（对于硫代烯酮本身，则是从三甲基甲硅烷基二硫代乙酸甲酯中获得）。还报道了结合这两个热解过程的丙二烯硫酮的合成。通过低温红外光谱法鉴定热分解产物，并立即用气态二甲胺淬灭，得到相应的硫代酰胺。在丙二烯硫酮的情况下，观察到与原位形成的甲硫醇的进一步反应。