2-(1-hydroxy-2,2-dimethylpropyl)phenol | 146256-23-7

• 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-(1-hydroxy-2,2-dimethylpropyl)phenol
• 英文别名: 2-(2,2-dimethyl-1-hydroxypropyl)phenol
• CAS: 146256-23-7
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: RELDEUPRKCEJSU-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  272.5±7.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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-(1-hydroxy-2,2-dimethylpropyl)phenol 在 乙酰丙酮 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以54%的产率得到2,3,3-trimethyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  One-Pot Synthesis of 4H-Chromenes by Tandem Benzylation and Cyclization in the Presence of Sodium Bisulfate on Silica Gel

  摘要：

  A simple and efficient method has been developed for the synthesis of 4H-chromenes from o-hydroxybenzylic alcohols and dicarbonyl compounds containing active methylene groups by using silica gel supported sodium bisulfate. Various dicarbonyl compounds such as diketones, keto esters, and keto amides can be used in the synthesis of the 4H-chromenes.

  DOI：

  10.1055/s-0033-1339026
• 作为产物：
  描述：

  特戊醛 在 盐酸 、 萘 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 6.75h， 生成 2-(1-hydroxy-2,2-dimethylpropyl)phenol
  参考文献：
  名称：

  Naphthalene-catalysed lithiation of functionalized chloroarenes: regioselective preparation and reactivity of functionalized lithioarenes

  摘要：

  The lithiation of different functionalized chloroarenes (dichlorobenzenes 1 and 3. mono and dichlorophenols 9 and 14, and chloropivalanilides 18) in the presence of a catalytic amount of naphthalene leads to the corresponding functionalized lithioarenes, which react with electrophiles to give the expected polyfunctionalized aromatic molecules 2, 4, 10. 19, 21, 22 and 24 in a regioselective manner. In the case of starting from chlorinated phenols or anilides a deprotonation of the functional group is carried out prior to the lithiation process; only for 2-chloropivalanilide 18o a coupling reaction leading to 2-n-butylpivalanilide is observed when an excess of n-butyllithium is used in the deprotonation step.

  DOI：

  10.1016/s0040-4020(01)80314-8

文献信息

• Low-energy collision-induced fragmentation of negative ions derived fromortho-,meta-, andpara-hydroxyphenyl carbaldehydes, ketones, and related compounds
  作者：Athula B. Attygalle、Josef Ruzicka、Deepu Varughese、Jason B. Bialecki、Sayed Jafri

  DOI：10.1002/jms.1252

  日期：2007.9

  2-hydroxy-1-naphthaldehyde, both of which show two consecutive CO eliminations, specifically lose the carbonyl oxygen first, followed by that of the phenolic group. Anions from 2-hydroxyphenyl alkyl ketones lose a ketene by a hydrogen transfer predominantly from the alpha position. Interestingly, a very significant charge-remote 1,4-elimination of a H(2) molecule was observed from the anion derived from 2,4-dihydroxybenzaldehyde

  记录了几种羟基苯基甲醛和酮产生的阴离子的碰撞诱导解离（CID）质谱，并进行了机械合理化。例如，去质子化的邻羟基苯甲醛的m / z 121离子光谱在m / z 93处显示一个强烈的峰，表明一氧化碳的损失归因于由电荷定向的杂化断裂机制介导的邻位效应。相反，衍生自间位和对位异构体的m / z 121离子经过电荷远程均质裂解以消除* H并形成distonic阴离子自由基，最终使CO丢失，从而在m / z 92处出现一个峰。对于对位异构体，这种两步均质机制是最主要的片段化途径。另一方面，间位异构体的光谱 图1b显示了分别在m / z 92和93处的两个主要峰，分别代表了同质和异质碎片。（18）O-同位素标记研究证实，从间羟基苯甲醛的阴离子中消除的CO分子中的氧源自醛基或酚基。相反，邻羟基苯甲醛和2-羟基-1-萘醛的阴离子，都显示出连续的两次CO消除，首先是先失去羰​​基氧，然后才失去酚基团的羰基氧。
• A Simple Synthesis of Densely Substituted Benzofurans by Domino Reaction of 2-Hydroxybenzyl Alcohols with 2-Substituted Furans
  作者：Anton S. Makarov、Anna E. Kekhvaeva、Petrakis N. Chalikidi、Vladimir T. Abaev、Igor V. Trushkov、Maxim G. Uchuskin

  DOI：10.1055/s-0039-1690000

  日期：2019.10

  Brönsted acid-catalyzed cascade synthesis of densely substituted benzofurans from easily available salicyl alcohols and biomass-derived furans has been developed. The disclosed sequence includes the intermediate formation of 2-(2-hydroxybenzyl)furans that quickly rearrange into functionalized benzofurans. The established protocol was applied for the total synthesis of sugikurojinol B. The Brönsted

  抽象的 已经开发了布朗斯台德酸催化的级联反应，该反应由易于获得的水杨醇和生物质衍生的呋喃进行稠合取代的苯并呋喃的级联反应。公开的序列包括2-（2-羟基苄基）呋喃的中间体形成，其快速重排为官能化的苯并呋喃。已建立的方案适用于sugikurojinol B的全合成。 已经开发了布朗斯台德酸催化的级联反应，该反应由易于获得的水杨醇和生物质衍生的呋喃进行稠合取代的苯并呋喃的级联反应。公开的序列包括2-（2-羟基苄基）呋喃的中间体形成，其快速重排为官能化的苯并呋喃。已建立的方案适用于sugikurojinol B的全合成。
• Ferrocene-Decorated Phenol Derivatives by Trapping <i>ortho</i> -Quinone Methide Intermediates with Ferrocene
  作者：Silvia González-Pelayo、Enol López、Javier Borge、Noemí de-los-Santos-Álvarez、Luis A. López

  DOI：10.1002/ejoc.201800396

  日期：2018.6.15

  The InCl3‐catalyzed reaction of ortho‐hydroxybenzyl alcohols with ferrocene provided ferrocenyl phenols. Control experiments support the participation of ortho‐quinone methides as key intermediates. A preliminary study revealed that some of the functionalized ferrocene derivatives prepared display significant cytotoxicity against various cancer cell lines.

  邻羟基苄醇与二茂铁的InCl 3催化反应提供了二茂铁基苯酚。对照实验支持邻醌甲基化物作为关键中间体的参与。初步研究表明，所制备的某些功能化二茂铁衍生物对各种癌细胞系显示出显着的细胞毒性。
• Visible-light-catalyzed synthesis of 1,3-benzoxazines <i>via</i> formal [4 + 2] cycloaddition of oximes with <i>o</i>-hydroxybenzyl alcohols
  作者：Zhenjie Qi、Zhenyu An、Bingbing Huang、Mingzhong Wu、Quansen Wu、Dongfang Jiang

  DOI：10.1039/d3ob00882g

  日期：——

  formal [4 + 2] cycloaddition of oximes with o-hydroxybenzyl alcohols was developed to easily synthesize diverse 1,3-benzoxazine derivatives. This synthesis was achieved under visible light-based organocatalytic and TsOH conditions. The reaction proceeds through the photoisomerization of oximes via visible light-mediated energy transfer, followed by the nucleophilic attack of o-QMs to oximes as a 1,2-dipole

  开发了肟与邻羟基苯甲醇的正式[4 + 2]环加成反应，可以轻松合成多种1,3-苯并恶嗪衍生物。该合成是在基于可见光的有机催化和 TsOH 条件下实现的。该反应通过可见光介导的能量转移进行肟的光异构化，然后邻-QMs对肟作为1,2-偶极合成子进行亲核攻击、环化和异构化。该反应具有广泛的底物范围，并且可以在温和的条件下进行。为了证明其合成用途，进行了克级反应，并将所得的 1,3-苯并恶嗪产品进一步转化为其他有价值的化合物。
• Novel Syntheses of 2,3-Disubstituted Benzofurans
  作者：Alan R. Katritzky、Yu Ji、Yunfeng Fang、Indra Prakash

  DOI：10.1021/jo010278p

  日期：2001.8.1