2-[(1Z)-3-羟基-3-甲基-1-丁烯-1-基]苯酚 | 17235-14-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 中文名称: 2-[(1Z)-3-羟基-3-甲基-1-丁烯-1-基]苯酚
• 英文名称: (Z)-2-(3-hydroxy-3-methylbut-1-en-1-yl)phenol
• 英文别名: (Z)-4-(2-hydroxyphenyl)-2-methyl-3-buten-2-ol；(Z)-4-(o-hydroxyphenyl)-2-methylbut-3-en-2-ol；2-((Z)-3-hydroxy-3-methylbut-1-enyl)-phenol；(Z)-o-(3-hydroxy-3-methylbut-1-enyl)phenol；2-methyl-4c-(2-hydroxy-phenyl)-buten-(3)-ol-(2)；3-(o-Hydroxyphenyl)-1,1,-dimethyl-propen-(2)-ol-(1)；Phenol, 2-(3-hydroxy-3-methyl-1-butenyl)-, (Z)-；2-[(Z)-3-hydroxy-3-methylbut-1-enyl]phenol
• CAS: 17235-14-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: CDSUBTCQAOYVRG-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2907299090

反应信息

• 作为反应物：
  描述：

  2-[(1Z)-3-羟基-3-甲基-1-丁烯-1-基]苯酚 在 acetylacetonatodicarbonylrhodium(l) 氢气 、 对甲苯磺酸 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 60.0 ℃ 、5.0 MPa 条件下， 反应 67.0h， 生成 2,3,3a,8a-tetrahydro-2,2-dimethylfuro[2,3-b]benzofuran
  参考文献：
  名称：

  Synthesis of Furo[2,3b]furans and Furo[2,3b]pyrans via Rhodium-Catalyzed Tandem Hydroformylation/Acetalization

  摘要：

  GRAPHICSRhodium-catalyzed tandem hydroformylation/acetalization of alpha,omega-alkenediols gives facile access to perhydrofuro[2,3b]furans and perhydrofuro[2,3b]pyrans in good yields. Similarly, benzoannelated tetrahydrofuro[2,3b]furans are obtained by hydroformylation of o-hydroxy cinnamyl alcohols.

  DOI：

  10.1021/ol017083o
• 作为产物：
  描述：

  2,3-苯并呋喃 、 丙酮 在 4,4'-二叔丁基苯并 、 lithium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以45%的产率得到2-[(1Z)-3-羟基-3-甲基-1-丁烯-1-基]苯酚
  参考文献：
  名称：

  Stereoselective Reductive Opening of 2,3-Benzofuran − A Two-Step Synthesis of 2H-Chromenes Including Deoxycordiachromene

  摘要：

  DOI：

  10.1002/1099-0690(200108)2001:15<2809::aid-ejoc2809>3.0.co;2-t

文献信息

• 2<i>H</i>-Chromenes Generated by an Iron(III) Complex-Catalyzed Allylic Cyclization
  作者：L. Calmus、A. Corbu、J. Cossy

  DOI：10.1002/adsc.201500058

  日期：2015.5.4

  A straightforward method based on an iron(III) complex‐catalyzed cyclization of 2‐(1‐hydroxyallyl)phenols is reported to access a large variety of 2H‐chromenes. This method was applied to the total synthesis of a natural product, tephrowatsin B.

  据报道，一种基于铁（III）络合物催化的2-（1-羟基烯丙基）苯酚环化的简单方法可以使用多种2 H-色烯。该方法应用于天然产物替弗洛韦汀B的全合成。
• Amination of<i>o</i>-Alkenylphenols with Alkylamines via Photoinduced Proton Transfer
  作者：Masahide Yasuda、Tatsuya Sone、Kimiko Tanabe、Kensuke Shima

  DOI：10.1246/cl.1994.453

  日期：1994.3

  Irradiation of o-alkenylphenols with alkylamines resulted in Markovnikov-type amination to give o-(1-alkylaminoalkyl)phenols in relatively good yields. The photoamination was initiated by a proton transfer from the ammonium ion to the alkenyl group of o-alkenylphenolate anion in the excited state in the ion pair formed between the phenols and the amines. The resulting zwitter ion allowed the nucleophilic addition of the amine at the benzylic cation center.

  用烷基胺辐照邻烯基苯酚会产生马尔科夫尼科夫式胺化反应，从而得到邻(1-烷基氨基烷基)苯酚，产量相对较高。在酚和胺之间形成的离子对的激发态中，质子从铵离子转移到邻烯基苯酚阴离子的烯基，从而引发了光胺化反应。由此产生的齐聚物离子允许胺在苄基阳离子中心进行亲核加成。
• The Chemistry of Vitamin E. XXII. The Reaction between Grignard Reagents and Coumarins and Hydrocoumarins¹
  作者：Lee Irvin Smith、P. M. Ruoff

  DOI：10.1021/ja01858a040

  日期：1940.1
• Reaction of 3-halogeno-2H-1-benzopyran-2-ones with organometallic compounds. Synthesis of 4-Alkyl-2H-1-benzopyran-2-ones. X-Ray molecular structure of 3-bromo-3,4-dihydro-4-isopropylcoumarin
  作者：Angel Alberola、Blanca Calvo、Alfonso Gonzalez Ortega、Martina Vicente、Santiago G. Granda、Juan F. Van der Maelen

  DOI：10.1039/p19910000203

  日期：——

  3-Halogeno-2H-1-benzopyran-2-ones react with magnesium, lithium, aluminium and copper derivatives to give 3,4-dihydrocoumarins and 3-(o-hydroxyphenyl)propenols as major products. The nature and the ratio of the products in the final mixture depend on the solvent and on the organometallic reagent. Grignard derivatives yield 1,4-monoalkylation compounds in tetrahydrofuran (THF) or 1,2-dialkylation derivatives in toluene. In some cases the dehalogenation competes with the 1,2-alkylation process in the reactions with alkyllithiums. The presence of the halogen at C-3 increases the reductive ability of organoaluminiums. In general, the reaction with lithium dialkylcuprates leads to complex mixtures of products. The 4-alkyl-3-halogeno-3,4-dihydrocoumarins obtained undergo dehydrohalogenation easily, and lead to 4-alkylcoumarins in good yields. The tandem alkylation-dehydrohalogenation of 3-halogeno-2H-1-benzopyran-2-ones constitutes a versatile synthesis of 4-alkylcoumarins.
• Yasuda, Masahide; Sone, Tatsuya; Tanabe, Kimiko, Journal of the Chemical Society. Perkin transactions I, 1995, # 4, p. 459 - 464
  作者：Yasuda, Masahide、Sone, Tatsuya、Tanabe, Kimiko、Shima, Kensuke

  DOI：——

  日期：——