2-(2'-hydroxyphenyl)-α,α-dimethylbenzyl alcohol | 134906-87-9

• 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: 2-(2'-hydroxyphenyl)-α,α-dimethylbenzyl alcohol
• 英文别名: 2-(2'-hydroxy-biphenyl-2-yl)-propan-2-ol；2-(α-Hydroxy-isopropyl)-biphenylol-(2')；2'-Hydroxy-2-(α-hydroxy-isopropyl)-biphenyl；o-(o-Hydroxyphenyl)-alpha,alpha-dimethylbenzyl alcohol；2-[2-(2-hydroxypropan-2-yl)phenyl]phenol
• CAS: 134906-87-9
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: HTJGXJKREAVBFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  147-150 °C
• 沸点：
  392.2±30.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2'-hydroxyphenyl)-α,α-dimethylbenzyl alcohol 在 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 以1.228 g的产率得到6,6-dimethyl-6H-benzo[c]chromene
  参考文献：
  名称：

  A General Synthetic Route to 6,6-Substituted-6H-dibenzo[b,d]pyrans from Dibenzofuran

  摘要：

  The reaction of dibenzofuran 1, lithium pieces (2.2 equiv), and TMEDA (2.2 equiv) in dry ether under reflux led to a solution of the corresponding C, O-dilithiated intermediate 2 which, upon treatment with different ketones or aldehydes (0.8 equiv) at -78 degrees C, afforded, after hydrolysis and dehydration, 6,6-substituted-6H-dibenzo[b,d]pyrans 3 in good yields. The reaction undergoes reductive ring opening and cyclization, and the intermediate diol 4e was isolated.

  DOI：

  10.1021/jo061415r
• 作为产物：
  描述：

  二苯并呋喃 、 丙酮 在 四甲基乙二胺 、 lithium 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 2-(2'-hydroxyphenyl)-α,α-dimethylbenzyl alcohol
  参考文献：
  名称：

  A General Synthetic Route to 6,6-Substituted-6H-dibenzo[b,d]pyrans from Dibenzofuran

  摘要：

  The reaction of dibenzofuran 1, lithium pieces (2.2 equiv), and TMEDA (2.2 equiv) in dry ether under reflux led to a solution of the corresponding C, O-dilithiated intermediate 2 which, upon treatment with different ketones or aldehydes (0.8 equiv) at -78 degrees C, afforded, after hydrolysis and dehydration, 6,6-substituted-6H-dibenzo[b,d]pyrans 3 in good yields. The reaction undergoes reductive ring opening and cyclization, and the intermediate diol 4e was isolated.

  DOI：

  10.1021/jo061415r

文献信息

• Production of dibenzopyrans, their isomeric fluorenols and
  申请人：General Electric Company

  公开号：US03947468A1

  公开（公告）日：1976-03-30

  Phenols and thiophenols having an ortho-phenyl substituent react with most aldehydes and ketones in very strongly acidic liquid media to form a dibenzopyran or dibenzothiopyran. The dibenzopyrans, but not the dibenzothiopyrans, can be isomerized to their corresponding fluorenols. The pyran or thiopyran ring can be cleaved chemically or electrochemically to produce phenols and thiophenols which have an ortho substituent in the ortho position of the phenyl substituent of the starting phenol or thiophenol which is characteristic of the aldehyde or ketone reactant. These products as well as the fluorenols, being phenolic bodies, are useful as stabilizers and antioxidants.

  苯酚和硫酚含有一个邻位苯基取代基，在非常强酸性液体介质中与大多数醛和酮反应，形成二苯并吡喃或二苯并硫吡喃。二苯并吡喃可以异构化为相应的芴酚，但二苯并硫吡喃不行。吡喃或硫吡喃环可以化学或电化学裂解，产生苯酚和硫酚，其邻位苯基取代基位于起始苯酚或硫酚的苯基取代基的邻位，这是醛或酮反应物的特征。这些产物以及芴酚作为酚类物质，可用作稳定剂和抗氧化剂。
• Photocyclization of 2-(2'-hydroxyphenyl)benzyl alcohol and derivatives via o-quinonemethide type intermediates
  作者：C. G. Huang、Kathryn Anne Beveridge、Peter Wan

  DOI：10.1021/ja00020a033

  日期：1991.9

  A new photochemical reaction, the photocyclization of 2-(2'-hydroxyphenyl)benzyl alcohol (1) and derivatives to 6H-dibenzo[b,d]pyrans, is reported. The quantum yield for cyclization of 1 to give pyran 7 is 0.50 +/- 0.04 in aqueous solutions of pH > 10. At lower pH, PHI is significantly lower. For example at pH 7, PHI = 0.25 +/- 0.03. Results from investigations of structure-reactivity, pH effects, and fluorescence data suggest a mechanism in which the primary step involves ionization of the phenol moiety to phenolate in S1, which is probably followed by (or is concerted with) twisting of the phenyl rings to give a more planar species in the excited state. This is subsequently followed by (or is concerted with) a dehydroxylation step of the benzyl alcohol moiety (all on the S1 surface) to give an omicron-quinonemethide type intermediate 20 and deactivation back to the ground-state surface. Electrocyclic ring closure of this intermediate gives the observed pyran. Nucleophilic trapping of this electrophilic intermediate by solvent (e.g., MeOH) to give the methyl ether is also observed when photolysis is carried out in MeOH. The proposed reaction pathway is unprecedented: it takes advantage of the tendency of biphenyl systems to be planar in the excited state as well as the enhanced electron-donating effect of the phenolate anion, which is required for the dehydroxylation step.
• 326. Cannabis indica resin. Part IV. The synthesis of some 2 : 2-dimethyldibenzopyrans, and confirmation of the structure of cannabinol
  作者：R. S. Cahn

  DOI：10.1039/jr9330001400

  日期：——
• The Cyclic Dehydration of Biphenyl Derivatives to Fluorenes
  作者：Marjorie Anchel、A. H. Blatt

  DOI：10.1021/ja01852a045

  日期：1941.7
• US3947468A
  申请人：——

  公开号：US3947468A

  公开（公告）日：1976-03-30