1-(3,5-二甲基-4-羟基苯基)-3-苯基丙醇 | 143682-76-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-(3,5-二甲基-4-羟基苯基)-3-苯基丙醇
• 英文名称: 1-(3,5-dimethyl-4-hydroxyphenyl)-3-phenylpropanol
• 英文别名: 4-(1-Hydroxy-3-phenylpropyl)-2,6-dimethylphenol
• CAS: 143682-76-2
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: OKQANDBSROINQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1-(3,5-二甲基-4-羟基苯基)-3-苯基丙醇 在 lithium aluminium tetrahydride 、 三甲基溴硅烷 、 silver(l) oxide 作用下， 以 氘代氯仿 为溶剂， 反应 0.84h， 生成 2,6-Dimethyl-4-<(3-phenyl)propylidene>-2,5-cyclohexadien-1-one
  参考文献：
  名称：

  Formal [3+2]cycloaddition of benzylic cations with alkenes

  摘要：

  The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.

  DOI：

  10.1021/jo00048a029
• 作为产物：
  描述：

  (E)-1-(4-Hydroxy-3,5-dimethyl-phenyl)-3-phenyl-propenone 生成 1-(3,5-二甲基-4-羟基苯基)-3-苯基丙醇
  参考文献：
  名称：

  Synthesis of 4-Cinnamylidene-2,5-cyclohexadien-1-ones

  摘要：

  氢化铝锂（LAH）还原 4′-羟基查耳酮，然后脱水，得到 4-亚肉桂基-2,5-环己二烯-1-酮，收率为 19-42%。用 LAH 还原 4′-乙酰氧基查耳酮也能得到同样的产物，而且产率有所提高。

  DOI：

  10.1246/bcsj.51.3612

文献信息

• Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions
  作者：Steven R. Angle、Damian O. Arnaiz、James P. Boyce、Rogelio P. Frutos、Michael S. Louie、Heather L. Mattson-Arnaiz、Jon D. Rainier、Kenneth D. Turnbull、Wenjin Yang

  DOI：10.1021/jo00100a039

  日期：1994.10

  p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five- and seven-membered rings were also studied. Oxidation of 2,6-disubstituted phenols with Ag2O afforded the corresponding quinone methides. A wide range of cyclization terminators/nucleophiles were found to be effective in the cyclizations, including: allylsilane, beta-keto esters, furan, pyrrole, indole, and a number of alkenes. The yields of the cyclizations were generally high.
• Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+, J. Org. Chem, 59 (1994) N 21, S 6322-6337
  作者：Angle Steven R., Arnaiz Damian O., Boyce James P., Frutos Rogelio P., Lou+

  DOI：——

  日期：——
• KUROSAWA K.; HASHIBA A.; TAKAHASHI H., BULL. CHEM. SOC. JAP., 1978, 51, NO 12, 3612-3615
  作者：KUROSAWA K.、 HASHIBA A.、 TAKAHASHI H.

  DOI：——

  日期：——
• Formal [3+2]cycloaddition of benzylic cations with alkenes
  作者：Steven R. Angle、Damian O. Arnaiz

  DOI：10.1021/jo00048a029

  日期：1992.10

  The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.
• Synthesis of 4-Cinnamylidene-2,5-cyclohexadien-1-ones
  作者：Kazu Kurosawa、Atsuko Hashiba、Hirobumi Takahashi

  DOI：10.1246/bcsj.51.3612

  日期：1978.12

  Lithium aluminium hydride (LAH) reduction of 4′-hydroxychalcones, followed by dehydration, yielded 4-cinnamylidene-2,5-cyclohexadien-1-ones in 19–42% yields. The LAH reduction of 4′-acetoxychalcones also gave the same products in improved yields.

  氢化铝锂（LAH）还原 4′-羟基查耳酮，然后脱水，得到 4-亚肉桂基-2,5-环己二烯-1-酮，收率为 19-42%。用 LAH 还原 4′-乙酰氧基查耳酮也能得到同样的产物，而且产率有所提高。