1,1-dimethyl-9,10-diphenyl-1,2,3,4,9,10-hexahydro-9,10-epoxyanthracene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1-dimethyl-9,10-diphenyl-1,2,3,4,9,10-hexahydro-9,10-epoxyanthracene
• 英文别名: 10,10-dimethyl-1,8-diphenyl-15-oxatetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9(14)-tetraene
• 化学式: C₂₈H₂₆O
• 分子量: 378.514
• InChiKey: DFFFHSSUQSPXSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2,2-二甲基环己酮 在 正丁基锂 、 bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 1,1-dimethyl-9,10-diphenyl-1,2,3,4,9,10-hexahydro-9,10-epoxyanthracene
  参考文献：
  名称：

  通过双烯丙基镁对环烯醇三氟甲磺酸酯的去质子化反应生成环炔烃

  摘要：

  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 ...

  DOI：

  10.1039/c6cc09920c

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 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.