3-methyl-9,10-dihydrophenanthrene | 94484-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-methyl-9,10-dihydrophenanthrene
• 英文别名: 3-Methyl-9,10-dihydro-phenanthren
• CAS: 94484-28-3
• 化学式: C₁₅H₁₄
• 分子量: 194.276
• InChiKey: AORVTFWZBMYYRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-(3-methylbut-2-enyl)-2-(toluene-4-sulfonyl)-3,4-dihydro-2H-naphthalen-1-one 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 硝基甲烷 为溶剂， 反应 8.0h， 以73%的产率得到3-methyl-9,10-dihydrophenanthrene
  参考文献：
  名称：

  Synthesis of Substituted Benzenes via Bi(OTf)₃-Mediated Intramolecular Carbonyl Allylation of α-Prenyl or α-Geranyl β-Arylketosulfones

  摘要：

  Intramolecular carbonyl allylation of alpha-prenyl or alpha-geranyl beta-arylketosulfones 5 in the presence of molecule sieves (MS) affords substituted benzenes 6-7 in moderate to good yields. The facile transformation proceeds by a synthetic sequence starting with the alpha-prenylation or alpha-geranylation of 1 and the Bi(OTf)(3)-mediated annulation of 5 followed by a sequential desulfonative aromatization or then an intramolecular FriedelCrafts alkylation. A plausible mechanism has been studied and proposed.

  DOI：

  10.1021/acs.orglett.5b01461

文献信息

• Potassium <i>tert</i>-Butoxide Promoted Intramolecular Arylation via a Radical Pathway
  作者：Daniela Sustac Roman、Yoko Takahashi、André B. Charette

  DOI：10.1021/ol201160s

  日期：2011.6.17

  Potassium tert-butoxide mediated intramolecular cyclization of aryl ethers, amines, and amides was efficiently performed under microwave irradiation to provide the corresponding products in high regioisomeric ratios. The reaction proceeds via single-electron transfer to initiate the formation of an aryl radical, followed by a kinetically favored 5-exo-trig and subsequent ring expansion.

  钾叔丁醇介导的分子内的芳基醚，胺和酰胺的环化有效地在微波辐射下进行，以提供在高比率的区域异构体的相应的产品。该反应通过单电子转移进行以引发芳基的形成，随后是动力学上有利的5 -exo-trig和随后的扩环。
• Efficient Synthesis of 9-Aryldihydrophenanthrenes by a Cascade Reaction Involving Arynes and Styrenes
  作者：Sachin Suresh Bhojgude、Anup Bhunia、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1021/ol4033094

  日期：2014.2.7

  A mild, general, and transition-metal-free protocol for the synthesis of 9,10-dihydrophenanthrenes is reported. The aryne generated by the fluoride-induced,1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes an efficient cascade reaction initiated by the Diels-Alder reaction with the differently substituted styrenes leading to the formation of 9-aryl-9,10-dihydrophenanthrene derivatives in moderate to good yields.
• Skvarchenko,V.R. et al., Journal of general chemistry of the USSR, 1960, vol. 30, p. 56 - 61
  作者：Skvarchenko,V.R. et al.

  DOI：——

  日期：——