9,10-diphenyl-1,2,3,4,9,10-hexahydro-9,10-epoxyanthracene | 747-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9,10-diphenyl-1,2,3,4,9,10-hexahydro-9,10-epoxyanthracene
• 英文别名: 1,8-Diphenyl-15-oxatetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9(14)-tetraene
• CAS: 747-58-0
• 化学式: C₂₆H₂₂O
• 分子量: 350.46
• InChiKey: ZESBBHKEKCIZNO-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C (decomp)(Solv: ethanol (64-17-5); hexane (110-54-3))
• 沸点：
  492.2±34.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  9,10-diphenyl-1,2,3,4,9,10-hexahydro-9,10-epoxyanthracene 在 溶剂黄146 作用下， 生成 9a,10-Diphenyl-1,3,4,9a-tetrahydro-2H-anthracen-9-one
  参考文献：
  名称：

  Wittig,G.; Mayer,U., Chemische Berichte, 1963, vol. 96, p. 329 - 341

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(triethylsilyloxy)cyclohexene 在 potassium tert-butylate 、 四丁基氟化铵 、 二异丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 、 乙基苯 为溶剂， 反应 3.0h， 生成 9,10-diphenyl-1,2,3,4,9,10-hexahydro-9,10-epoxyanthracene
  参考文献：
  名称：

  从硅烷烯醇醚单环合成环己烯和1,2-环己二烯硅烷化烯醇三氟甲磺酸

  摘要：

  基于甲硅烷基的一锅重排，然后形成烯醇三氟甲磺酸，描述了用于应变环己炔和1,2-环己二烯的前体的区域控制合成。在室温下在一小时内，在化学计量的水存在下，将瞬态α-甲硅烷基化的烯酸锂平稳异构化，以提供环己炔的前体。

  DOI：

  10.1002/ejoc.201800353

文献信息

• Steric effects on deprotonative generation of cyclohexynes and 1,2-cyclohexadienes from cyclohexenyl triflates by magnesium amides
  作者：Yuto Hioki、Atsunori Mori、Kentaro Okano

  DOI：10.1016/j.tet.2020.131103

  日期：2020.5

  Steric effects on the deprotonative generation of cyclohexynes and 1,2-cyclohexadienes from cyclohexenyl triflates are described. A cyclohexenyl triflate, which is readily available from nonsubstituted cyclohexanone, was selectively converted to cyclohexyne using magnesium bis(2,2,6,6-tetramethylpiperidide) as base. The generated cyclohexyne was trapped by 1,3-diphenylisobenzofuran to afford the cycloadduct

  描述了对从环己烯基三氟甲磺酸酯产生的环己炔和1,2-环己二烯的去质子化的立体效应。使用二（2,2,6,6-四甲基哌啶镁）镁将可从非取代的环己酮容易获得的环己烯基三氟甲磺酸酯选择性地转化为环己炔。产生的环己炔被1，3-二苯基异苯并呋喃捕获，得到环加合物。该方法也适用于由α-四氢萘酮制备的苯并稠合的环己烯基三氟甲磺酸酯。将在3-位带有两个甲基取代基的环己烯基三氟甲磺酸酯选择性转化为相应的1,2-环己二烯。该1，2-环己二烯与1，3-二苯基异苯并呋喃，苯乙烯和硝酮反应，以高收率提供相应的环加合物。
• Generation of cycloalkynes through deprotonation of cyclic enol triflates with magnesium bisamides
  作者：Yuto Hioki、Kentaro Okano、Atsunori Mori

  DOI：10.1039/c6cc09920c

  日期：——

  Deprotonative generation of cyclohexynes, cycloheptynes, and cyclooctynes was achieved by controlling the reactivities of transient anionic species from corresponding enol triflates with magnesium bis(2,2,6,6-tetramethylpiperidide) as a base. The starting enol...

  通过控制镁（双（2,2,6,6-四甲基哌啶）镁）从相应的烯醇三氟甲磺酸盐中获得的瞬态阴离子物种的反应性，实现了己己，环庚炔和环辛炔的去质子化。起始enol ...
• Generation of Cycloalkylidene Carbenes via Exo-Type Cyclization of Alkynyllithiums Bearing Remote Leaving Group
  作者：Toshiro Harada、Katsuhiro Iwazaki、Takeshi Otani、Akira Oku

  DOI：10.1021/jo981411p

  日期：1998.11.1

  The reaction of 5-hexynyl tosylate (3a) with alkynyllithium (RC=CLi; R Ph, TMS) gives enynes 5 and 6. The reaction proceeds through a mechanism involving a novel exo-type cyclization of 6-lithiod-hexynyl tosylate to form cyclopentylidene carbene. Enyne 6 is produced by the addition of RC=CLi to the carbene, whereas rearrangement of the carbene to cyclohexyne followed by carbolithiation with RC=CLi gives enyne 5. The formation of cyclopentylidene carbene and cyclohexyne as intermediates is clearly demonstrated by trapping experiments with cyclohexene land triethylsilane) and with 1,3-diphenylisobenzofuran, respectively. Alkynyllithiums derived from 3-butynyl and 6-heptynyl p-fluorobenzenesulfonates (19a,b) undergo a similar exo-type cyclization to give cyclopropylidene and cyclohexylidene carbenes, respectively.
• Bi-3H-diazirin-3-yls as Precursors of Highly Strained Cycloalkynes
  作者：Mohammad Al-Omari、Klaus Banert、Manfred Hagedorn

  DOI：10.1002/anie.200503124

  日期：2006.1
• Cyclohexynes as intermediates in a novel endo-cyclization of alkynylzincates derived from 5-hexynyl tosylates
  作者：Toshiro Harada、Takeshi Otani、Akira Oku

  DOI：10.1016/s0040-4039(97)00481-4

  日期：1997.4

  The pi-type endo-cyclization of metal acetylides to form cyclohexynes was observed for the first time in the reaction of alkynylzincates derived from 5-hexynyl tosylates. The endo-cyclization took place in competition with exo-cyclization, leading to the formation of 1-(cyclopentylidene)alkylzincs. (C) 1997 Elsevier Science Ltd.