α-(tert-butyl)-2-methoxyphenylmethanol | 53847-36-2

• 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: α-(tert-butyl)-2-methoxyphenylmethanol
• 英文别名: α-tert-butyl-2-methoxybenzyl alcohol；1-(2-methoxyphenyl)-2,2-dimethylpropan-1-ol；2,2-dimethyl-1-(2-methoxyphenyl)-1-propanol
• CAS: 53847-36-2
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: HNWGZBPWSQYULK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-(tert-butyl)-2-methoxyphenylmethanol 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 50.0 ℃ 、413.69 kPa 条件下， 反应 90.0h， 以67%的产率得到1-methoxy-2-neopentylbenzene
  参考文献：
  名称：

  [EN] 2-ARYLOXYETHYL GLYCINE DERIVATIVES AND THEIR USE AS GLYCINE TRANSPORT INHIBITORS
  [FR] DERIVES DE LA 2-ARYLOXYETHYL GLYCINE ET LEUR UTILISATION COMME INHIBITEURS DU TRANSPORT DE LA GLYCINE

  摘要：

  本发明涉及某些2-芳氧基乙基甘氨酸衍生物，它们作为甘氨酸类型-1转运体的抑制剂具有活性，涉及含有它们的药物组合物，以及它们在治疗神经学和神经精神障碍中的用途。

  公开号：

  WO2005100301A1
• 作为产物：
  描述：

  1-(2-甲氧基苯基)-2,2-二甲基-1-丙酮 在 sodium tetrahydroborate 作用下， 生成 α-(tert-butyl)-2-methoxyphenylmethanol
  参考文献：
  名称：

  手性三齿配体的钌配合物催化的大体积酮的对映选择性加氢和转移加氢

  摘要：

  报道了对一类新型三齿-Ru配合物催化的叔烷基酮的对映选择性加氢的研究。与广泛研究的[RuCl 2（diphos）（二伯胺）]配合物相比，这种新型的氢化催化剂可将这些反应性较低的笨重酮平稳还原，其ee最高可达94％ 。相同的催化剂体系还可以选择性地还原其他潜在有问题的底物，例如庞大的杂环酮。通常对于加压氢化催化剂，在转移氢化条件下可以获得相似的对映选择性。转移氢化比压力氢化稍慢，但是这个缺点很容易克服，因为我们发现上述酮的微波加速转移氢化在约90°C的20分钟内发生，其选择性与在压力下获得的选择性相似。氢化系统。

  DOI：

  10.1002/chem.200801929

文献信息

• Intramolecular Hydrogen Bonding and Conformations of α,α-Dialkyl-and α-Alkyl-<i>o</i>-methoxybenzyl Alcohols
  作者：Akihiko Yamashita、Katsuo Hara、Shigeko Aizawa、Minoru Hirota

  DOI：10.1246/bcsj.47.2508

  日期：1974.10

  The stable conformations of α-alkyl- and α,α-dialkyl-o-methoxybenzyl alcohols were deduced by measurement of their infrared and PMR spectra. Population of these conformations was estimated from the intensities of the O–H stretching bands of the free and the hydrogen-bonded species. The O–H chemical shifts at infinite dilution (δOH∞) of the free and the hydrogen-bonded species were determined by plotting the δOH∞ values against population obtained from the infrared spectra. An anomalous behavior was observed with the α-alkyl-α-t-butyl alcohols, which might be due to a buttressing effect.

  通过测量红外光谱和质子磁共振光谱，推导了α-烷基-和α,α-二烷基-邻甲氧基苄醇的稳定构象。这些构象的占据情况是通过自由物种和氢键物种的O-H伸缩带的强度来估计的。通过将自由物种和氢键物种的O-H化学位移（δOH∞）值与从红外光谱获得的占据情况作图，确定了它们的δOH∞。观察到了α-烷基-α-叔丁醇的异常行为，这可能是由于支撑效应导致的。
• Michael Additions of Highly Basic Enolates to <i>ortho</i>-Quinone Methides
  作者：Robert S. Lewis、Christopher J. Garza、Ann T. Dang、Te Kie A. Pedro、William J. Chain

  DOI：10.1021/acs.orglett.5b00972

  日期：2015.5.1

  which ketone or ester enolates and ortho-quinone methides (o-QMs) are generated in situ in a single reaction flask from silylated precursors under the action of anhydrous fluoride is reported. The reaction partners are joined to give a variety of β-(2-hydroxyphenyl)-carbonyl compounds in 32–94% yield in a single laboratory operation. The intermediacy of o-QMs is supported by control experiments utilizing

  据报道，在无水氟化物的作用下，由甲硅烷基化的前体在一个反应​​烧瓶中原位生成酮或酯的烯醇化物和邻-醌甲基化物（o -QMs）。通过一次实验室操作，即可将反应伙伴连接起来，以32-94％的收率得到各种β-（2-羟苯基）-羰基化合物。o -QM的中间性通过使用烯醇盐前体和常规烷基卤化物作为竞争性烷基化剂的控制实验以及由未恢复芳香族体系的共轭物加成分离的1,5-二羰基产物的支持得到支持。
• Chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane
  作者：Qiwen Zhou、Wei Meng、Xiangqing Feng、Haifeng Du、Jing Yang

  DOI：10.1016/j.tetlet.2019.151394

  日期：2020.1

  An asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane was successfully realized with chiral phosphoric acid (CPA) as catalyst and water as additive. A variety of optically active secondary alcohols were obtained in good to high yields with up to 77% ee. The reaction likely proceeded through a Brønsted acid-promoted double-hydrogen transfer between ketones and ammonia borane

  以手性磷酸（CPA）为催化剂，水为添加剂，成功实现了氨硼烷对大体积芳基酮的不对称转移加氢反应。以高至高收率获得了多种旋光仲醇，ee高达77％。该反应可能是通过布朗斯台德酸促进的双氢在酮和氨硼烷之间的六元一致过渡态转移而进行的。
• NOVEL NANOCARRIER DELIVERED CANCER CHEMOTHERAPEUTIC AGENTS
  申请人：UNIVERSITY OF CINCINNATI

  公开号：US20160101188A1

  公开（公告）日：2016-04-14

  Compositions and methods for treating cancer in a subject are described herein. The composition includes modified nucleobases and nucleosides that are converted in the cell to nucleotides that are incorporated into growing DNA and result in termination of DNA elongation. The nucleobases and nucleotides are incorporated with a drug delivery system (DDS). The DDS includes β-cyclodextrin. The nucleobases and nucleotides are conjugated to the β-cyclodextrin by an acid labile linker that releases the nucleobases and nucleotides in the acidic environment of cancer cells. The DDS may also include a targeting ligand that targets the DDS/nucleobase or nucleotide conjugate to cancer cells. The DDS/nucleobase or nucleotide conjugate may self form into nanoparticles and may be administered to a subject with cancer in an amount effective to treat said cancer.

  本文描述了用于治疗患者癌症的组合物和方法。该组合物包括经过修饰的核碱基和核苷，这些核碱基和核苷在细胞中转化为核苷酸，并被合并到正在生长的DNA中，导致DNA延伸终止。这些核碱基和核苷与药物输送系统（DDS）一起使用。DDS包括β-环糊精。核碱基和核苷通过酸敏链连接到β-环糊精上，该链在癌细胞的酸性环境中释放核碱基和核苷。DDS还可以包括靶向配体，将DDS/核碱基或核苷共轭物靶向癌细胞。DDS/核碱基或核苷共轭物可以自行形成纳米粒子，并可以以有效治疗癌症的剂量给患者服用。
• Deprotonative metalation of aromatic compounds using mixed lithium–iron combinations
  作者：Elisabeth Nagaradja、Floris Chevallier、Thierry Roisnel、Viatcheslav Jouikov、Florence Mongin

  DOI：10.1016/j.tet.2012.02.019

  日期：2012.4

  The deprotonation of 2-methoxypyridine was attempted using putative (TMP)(3)FeLi prepared from different iron sources. Using iodine to intercept the metalated 2-methoxypyridine, the best result was obtained from FeBr2 (1 equiv) using THF at room temperature: nevertheless, in addition to the expected iodide, the corresponding 2,2'-dimer was obtained (86% total yield). The origin of the competitive formation of the 2,2'-dimer was not identified but mechanisms were suggested to explain its formation. It was observed that the nature of the electrophile employed to trap the 3-metalated 2-methoxypyridine has a strong impact on this dimer formation, the latter being favored using iodine (35% yield), but also benzophenone (28%), benzoyl chloride (22%), methyl iodide (27%), allyl bromide (15%), benzyl bromide (41%), and tetramethylthiuram disulphide (36%); for this reason, the yields of the expected derivatives were only 51, 15, 62, 0, <5, 18, and 0%, respectively. In contrast, using aldehydes readily led to the expected pyridine alcohols without dimerization (59% yield using 3,4,5-trimethoxybenzaldehyde and 66% yield using pivalaldehyde). 2,6-Dimethoxypyridine (in 68% yield), anisole (47%), 2,4-dimethoxypyrimidine (50% at C5 and 3% at C6), 2-fluoropyridine (64%), and thiophene (49%) were similarly converted into the corresponding alcohols after subsequent trapping with pivalaldehyde. Using iodine to trap the 2-metalated anisole did not lead to dimer formation, and 2-iodoanisole was isolated in 71% yield. (C) 2012 Elsevier Ltd. All rights reserved.