1-(4-fluorophenyl)-1,2-dihydronaphthalene | 1346149-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-fluorophenyl)-1,2-dihydronaphthalene
• 英文别名: 1-(4-Fluorophenyl)-1,2-dihydronaphthalene
• CAS: 1346149-39-0
• 化学式: C₁₆H₁₃F
• 分子量: 224.278
• InChiKey: RMKBFRSVNLHPEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟乙醇 、 1-(4-fluorophenyl)-1,2-dihydronaphthalene 在 羟基甲苯磺酰碘苯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 1-(bis(2,2,2-trifluoroethoxy)methyl)-3.(4.fluorophenyl)-2,3-dihydro-1H-indene 、 1-(bis(2,2,2-trifluoroethoxy)methyl)-3.(4.fluorophenyl)-2,3-dihydro-1H-indene
  参考文献：
  名称：

  Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes

  摘要：

  A metal-free protocol was developed to synthesize indanes by ring contraction of 1,2-dihydronaphthalenes promoted by PhI(OH) OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2,2,2-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), and a 1: 4 mixture of TFE: CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1,3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry.

  DOI：

  10.1590/s0103-50532011000900024
• 作为产物：
  描述：

  4-(4-fluorophenyl)-3,4-dihydro-1(2H)-naphthalen-1-one 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.5h， 生成 1-(4-fluorophenyl)-1,2-dihydronaphthalene
  参考文献：
  名称：

  Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes

  摘要：

  A metal-free protocol was developed to synthesize indanes by ring contraction of 1,2-dihydronaphthalenes promoted by PhI(OH) OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2,2,2-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), and a 1: 4 mixture of TFE: CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1,3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry.

  DOI：

  10.1590/s0103-50532011000900024

文献信息

• Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
  作者：Fernanda A Siqueira、Eloisa E Ishikawa、André Fogaça、Andréa T Faccio、Vânia M. T Carneiro、Rafael R. S Soares、Aline Utaka、Iris R. M Tébéka、Marcin Bielawski、Berit Olofsson、Luiz F Silva Jr

  DOI：10.1590/s0103-50532011000900024

  日期：——

  A metal-free protocol was developed to synthesize indanes by ring contraction of 1,2-dihydronaphthalenes promoted by PhI(OH) OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2,2,2-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), and a 1: 4 mixture of TFE: CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1,3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry.