2',3'-dimethyl-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-ol | 1237740-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2',3'-dimethyl-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-ol
• CAS: 1237740-80-5
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: JKJZUNHPWXLSHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2',3'-dimethyl-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-ol 、 2-(2,3-dimethylcyclohex-1-enyl)phenol 、 甲基磺酰氯 在 三乙胺 、 iron(III) chloride 、 palladium dichloride 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 2.08h， 以3.2 g的产率得到2-(2,3-dimethylcyclohex-1-enyl)phenyl methanesulfonate
  参考文献：
  名称：

  Synthesis of Substituted Chromanones: An Organocatalytic Aldol/oxa-Michael Reaction

  摘要：

  A diastereoselective organocatalytic aldol/oxa-Michael reaction has been developed to efficiently deliver medicinally relevant 2,3-ring-substituted chromanones. Development of this synthetic strategy revealed an unexpected kinetic anti-Saytzeff elimination; an origin for the observed selectivity is suggested on the basis of the results of quantum chemical calculations. This unusual kinetic selectivity necessitated an isomerization protocol that in turn led to the discovery of an intriguing Pd-mediated isomerization/intramolecular Friedel-Crafts-type alkylation.

  DOI：

  10.1021/ol101221c
• 作为产物：
  描述：

  2-溴苯酚 、 2,3-二甲基环己烷-1-酮 在 正丁基锂 、 盐酸 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 16.0h， 生成 2',3'-dimethyl-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-ol 、 2-(2,3-dimethylcyclohex-1-enyl)phenol
  参考文献：
  名称：

  Synthesis of Substituted Chromanones: An Organocatalytic Aldol/oxa-Michael Reaction

  摘要：

  A diastereoselective organocatalytic aldol/oxa-Michael reaction has been developed to efficiently deliver medicinally relevant 2,3-ring-substituted chromanones. Development of this synthetic strategy revealed an unexpected kinetic anti-Saytzeff elimination; an origin for the observed selectivity is suggested on the basis of the results of quantum chemical calculations. This unusual kinetic selectivity necessitated an isomerization protocol that in turn led to the discovery of an intriguing Pd-mediated isomerization/intramolecular Friedel-Crafts-type alkylation.

  DOI：

  10.1021/ol101221c