4'-(1,3-dioxolan-2-yl)-[1,1'-biphenyl]-2-ol | 400745-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-(1,3-dioxolan-2-yl)-[1,1'-biphenyl]-2-ol
• 英文别名: 4'-(1,3-Dioxolan-2-yl)[1,1'-biphenyl]-2-ol；2-[4-(1,3-dioxolan-2-yl)phenyl]phenol
• CAS: 400745-49-5
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: RTPQTQMCOXMANB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-(1,3-dioxolan-2-yl)-[1,1'-biphenyl]-2-ol 在 3-硝基吡啶 、 过氧化苯甲酸叔丁酯 、 palladium diacetate 作用下， 以 1,3-二甲基-2-咪唑啉酮 、 六氟苯 为溶剂， 反应 4.0h， 以55%的产率得到3-(1,3-dioxolan-2-yl)dibenzo[b,d]furan
  参考文献：
  名称：

  Oxidative Cyclization of 2-Arylphenols to Dibenzofurans under Pd(II)/Peroxybenzoate Catalysis

  摘要：

  2-Arylphenols undergo intramolecular C-H bond activation/C-O bond formation to afford dibenzofuran derivatives under palladium catalysis In the presence of tert-butyl peroxybenzoate as an oxidant. Kinetic isotope effect experiments indicated that C-H bond cleavage Is the rate-limiting step of the reaction.

  DOI：

  10.1021/ol202229w
• 作为产物：
  描述：

  2-(4-溴苯基)-1,3-二氧戊环 、 2-羟基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 5.0h， 以74%的产率得到4'-(1,3-dioxolan-2-yl)-[1,1'-biphenyl]-2-ol
  参考文献：
  名称：

  Oxidative Cyclization of 2-Arylphenols to Dibenzofurans under Pd(II)/Peroxybenzoate Catalysis

  摘要：

  2-Arylphenols undergo intramolecular C-H bond activation/C-O bond formation to afford dibenzofuran derivatives under palladium catalysis In the presence of tert-butyl peroxybenzoate as an oxidant. Kinetic isotope effect experiments indicated that C-H bond cleavage Is the rate-limiting step of the reaction.

  DOI：

  10.1021/ol202229w

文献信息

• Synthesis of Dibenzopyranones through Palladium-Catalyzed Directed C-H Activation/Carbonylation of 2-Arylphenols
  作者：Shuang Luo、Fei-Xian Luo、Xi-Sha Zhang、Zhang-Jie Shi

  DOI：10.1002/anie.201304295

  日期：2013.9.27

  Dibenzopyranones were synthesized by a palladium‐catalyzed phenol‐directed C–H activation/carbonylation of 2‐phenylphenol derivatives in the presence of CO. Pd(OAc)2 was used as a catalyst and Cu(OAc)2 as a catalytic oxidant in the presence of air.

  二苯并吡喃酮是在CO存在下，通过钯催化的苯酚引导的2-苯基苯酚衍生物的C–H活化/羰基化反应合成的。Pd（OAc）2作为催化剂，Cu（OAc）2作为催化剂氧化剂。空气的存在。
• Synthesis of Dibenzofurans via Palladium-Catalyzed Phenol-Directed C–H Activation/C–O Cyclization
  作者：Bin Xiao、Tian-Jun Gong、Zhao-Jing Liu、Jing-Hui Liu、Dong-Fen Luo、Jun Xu、Lei Liu

  DOI：10.1021/ja203335u

  日期：2011.6.22

  A practical, Pd(0)/Pd(II)-catalyzed reaction was developed for phenol-directed C-H activation/C-O cyclization using air as an oxidant. The turnover-limiting step of the process was found to be C-O reductive elimination instead of C-H activation. This reaction can tolerate a variety of functional groups and is complementary to the previous methods for the synthesis of substituted dibenzofurans.
• Oxidative Cyclization of 2-Arylphenols to Dibenzofurans under Pd(II)/Peroxybenzoate Catalysis
  作者：Ye Wei、Naohiko Yoshikai

  DOI：10.1021/ol202229w

  日期：2011.10.21

  2-Arylphenols undergo intramolecular C-H bond activation/C-O bond formation to afford dibenzofuran derivatives under palladium catalysis In the presence of tert-butyl peroxybenzoate as an oxidant. Kinetic isotope effect experiments indicated that C-H bond cleavage Is the rate-limiting step of the reaction.