4-(2-methyl-5-hydroxyphenyl)butanal | 97400-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-methyl-5-hydroxyphenyl)butanal
• 英文别名: 4-(5'-hydroxy-2'-methylphenyl)butanal；4-(5-Hydroxy-2-methylphenyl)butanal
• CAS: 97400-51-6
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: DGJPSBXWBVWRDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-methyl-5-hydroxyphenyl)butanal 在 正丁基锂 、 碘化异丙基三苯鏻 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到1,8-Dihydroxy-5-methyl-tetralin
  参考文献：
  名称：

  通过逆羟醛反应进入 Curcuphenol/Elvirol 核心结构

  摘要：

  通过环二烯酮前体的芳构化反应和关键醛中间体的烯化反应，从烷基-α-四氢萘酮分六步制备姜黄酚/elvirol 的类似物，即天然存在的红没药烷倍半萜。还报道了 6a、6b、6d 和 6g 的体外抗真菌活性。

  DOI：

  10.1002/cbdv.201000160
• 作为产物：
  描述：

  acetic acid (1S*,8aS*)-(+/-)-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yl ester 在 氢氧化钾 、 苯亚硒酸酐 作用下， 以 甲醇 、 氯苯 为溶剂， 反应 5.5h， 生成 4-(2-methyl-5-hydroxyphenyl)butanal
  参考文献：
  名称：

  Waring, Anthony John; Zaidi, Javid Hussain, Journal of the Chemical Society. Perkin transactions I, 1985, p. 631 - 640

  摘要：

  DOI：

文献信息

• Preparation of phenyl-butyraldehydes using a base-catalyzed aromatization of dienones
  作者：María Fernanda Plano、Guillermo R. Labadie、Raquel M. Cravero

  DOI：10.1016/j.tetlet.2008.03.038

  日期：2008.4

  five-step sequence synthesis. The synthetic strategy involved the use of a novel aromatization reaction of dienones. These key intermediates were prepared following a sequence involving BAR of substituted tetralones, ketones reduction, protection of alcohol, and bis-allylic oxidation. The key step of the route is an aromatization promoted by basic reaction conditions of dienones leading to substituted 4-phenyl

  使用五步序列合成制备了七个醛。合成策略涉及使用二烯酮的新型芳构化反应。这些关键中间体是根据一系列涉及取代四氢萘酮的BAR，酮还原，醇的保护和双烯丙基氧化的顺序制备的。该路线的关键步骤是通过二烯酮的基本反应条件促进的芳构化，从而导致取代的4-苯基丁醛。
• An efficient approach toward the synthesis of the A/B rings of ouabain
  作者：María Fernanda Plano、Guillermo R. Labadie、Manuel Gonzalez Sierra、Raquel M. Cravero

  DOI：10.1016/j.tetlet.2006.08.047

  日期：2006.10

  The synthesis of the highly functionalized A/B ring related to ouabain has been accomplished efficiently from commercially available α-tetralone. A key Birch reductive alkylation allows the building of an angularly substituted decalone that was adequately functionalized to produce the intermediate 2c.

  已经从市售的α-四氢萘酮有效地完成了与哇巴因有关的高度官能化的A / B环的合成。关键的桦木还原烷基化反应可以构建成角度取代的十烯酮，该十烯酮具有足够的功能以生成中间体2c。
• Synthesis and photochemical rearrangements of bicyclic cross-conjugated cyclohexadienones containing .delta.-oxy substituents
  作者：Drury Caine、Pravin L. Kotian、Melisa D. McGuiness

  DOI：10.1021/jo00022a018

  日期：1991.10

  Several 6/5-fused cross-conjugated cyclohexadienones containing delta-oxy substituents on the B ring including the benzoyl, SEM, and TBDPS hydroxyl-protected systems 12b, 12f, and 12g were prepared from the corresponding enones by the phenylselenenylation-selenoxide elimination procedure. Attempted preparation of dienones 12a, 12c, and 12d containing tert-butyl, methyl, and trimethylsilyl hydroxyl-protecting groups failed. Instead, the phenolic aldehyde 13 was obtained after workup or column chromatography on silica gel. The THP-protected dienone 12e could be purified and characterized, but it gave aldehyde 13 on standing in acetic acid at room temperature. Irradiations of dienones 12b, 12f, and 12g in glacial acetic acid using a high-pressure mercury lamp housed in a Pyrex probe gave mixtures containing several photoproducts. The corresponding 5/6-fused acetoxy ketones 22a, 22c, and 22b were the major products in each case. The 5/6-fused hydroxy ketone 23 was also obtained from dienone 22a. Mixtures of tricyclic ketones of the type 27 and 28 resulting from rare examples of trapping of Zimmerman-Schuster cyclopropyl carbocation intermediates, i.e., 26, by the solvent were also obtained from all three dienones. Dienones 12g and 12f also gave tricyclic acetoxy ketones 31a and 31b, which presumably arose via a 1,4-sigmatropic rearrangement of an excited-state precursor of 26.
• WARING, A. J.;ZAIDI, JAVID, HUSSAIN, J. CHEM. SOC. PERKIN TRANS., 1985, N 3, 631-639
  作者：WARING, A. J.、ZAIDI, JAVID, HUSSAIN

  DOI：——

  日期：——