2-(2,4,6-Trimethylphenyl)-2-propanol | 59660-68-3

• 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-(2,4,6-Trimethylphenyl)-2-propanol
• 英文别名: 2-mesityl-2-propanol；2-(2,4,6-trimethyl-phenyl)propan-2-ol；2-(2,4,6-Trimethylphenyl)propan-2-ol
• CAS: 59660-68-3
• 化学式: C₁₂H₁₈O
• mdl: MFCD09260837
• 分子量: 178.274
• InChiKey: JFDXATFYWOLYQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  112.0-112.6 °C(Solv: methanol (67-56-1))
• 沸点：
  230.1±8.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,4,6-Trimethylphenyl)-2-propanol 在 硝酸 、 sodium carbonate 作用下， 以 甲酸 为溶剂， 生成 Isopropenylnitromesitylen
  参考文献：
  名称：

  Restricted Rotation in Aryl Amines. XXII. Effect of meta Substitution on the Optical Stability of Some N-Benzenesulfonyl-N-carboxymethylmesidines

  摘要：

  DOI：

  10.1021/ja01472a031
• 作为产物：
  描述：

  2,4,6-三甲基苯甲腈 在 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 2-(2,4,6-Trimethylphenyl)-2-propanol
  参考文献：
  名称：

  Ortho Methyl Group Effects in Cumyl Systems

  摘要：

  In an attempt to evaluate the steric effect of ortho methyl groups on the stability of the cumyl radical, 2,2',4,4',6,6'-hexamethylazocumene (6) was synthesized and its rate of decomposition was measured. The fact that 6 decomposes 40 times faster than azocumene is attributed to a ground state steric effect. Calculations on the mesitylcumyl radical 1 and cation 2 show both systems to be substantially nonplanar with dihedral angles of 48 degrees and 35 degrees, respectively. Calculated charge distributions for cation 2 corroborate previously obtained NMR results which showed substantial loss of charge delocalization.(1)

  DOI：

  10.1021/jo00121a057

文献信息

• Arylvanadium-verbindungen XI. Zur reaktion von trimesitylvanadium mit ketonen
  作者：G. Kreisel、W. Seidel

  DOI：10.1016/s0022-328x(00)99479-8

  日期：1984.1

  Trimesitylvanadium in solution reacts with a series of ketones. Depending upon the structures of the ketones these reactions yield olefins, alcohols or a radical, respectively. Sterically hindered ketones only form coordination compounds with trimesitylvanadium or do not react at all.

  溶液中的Trimesitylvanadium与一系列酮反应。根据酮的结构，这些反应分别产生烯烃，醇或自由基。受阻位酮仅与三苯甲基钒形成配位化合物，或根本不发生反应。
• Solutions of anhydrous lanthanide salts and its preparation
  申请人：Ludwig-Maximilians-Universität München

  公开号：EP1759765A1

  公开（公告）日：2007-03-07

  The present invention relates to anhydrous solutions of MX3•z LiA in a solvent, wherein M is a lanthanide including lanthanum, or yttrium or indium; z > 0; and X and A are independently or both monovalent anions, preferably Cl, Br or I. The solution is readily prepared by dissolving or suspending MX3 or its hydrate and z equiv LiA in water or hydrophilic solvents, or mixtures thereof, removing the solvent under vacuum and dissolving the resulting powder in another solvent. The solution of MX3•z LiA can advantageously be used e.g. in addition reactions of Grignard reagents to ketones and imines. Even the catalytic use of MX3•z LiA is possible. Also claimed are a method for preparing the anhydrous solutions, the use of such solution in a chemical reaction and chemical compositions MX3•z LiA, with M, z, X and A as indicated above.

  本发明涉及MX3•z LiA在溶剂中的无水溶液，其中M是镧系元素包括镧或钇或铟；z > 0；X和A分别或同时是一价阴离子，优选为Cl、Br或I。该溶液可通过在水或亲水性溶剂中溶解或悬浮MX3或其水合物和z当量的LiA，然后在真空下去除溶剂并将得到的粉末溶解在另一溶剂中而轻松制备。MX3•z LiA的溶液可以有益地用于例如Grignard试剂对酮和亚胺的加成反应。甚至可以进行MX3•z LiA的催化使用。 还声明了一种制备无水溶液的方法，以及在化学反应中使用这种溶液和化学组合物MX3•z LiA，其中M、z、X和A如上所示。
• Reactions of carbonyl compounds with Grignard reagents in the presence of cerium chloride
  作者：Tsuneo Imamoto、Nobuyuki Takiyama、Kimikazu Nakamura、Toshihiko Hatajima、Yasuo Kamiya

  DOI：10.1021/ja00194a037

  日期：1989.6

  The addition of Grignard reagents to ketones is significantly enhanced by cerium chloride with remarkable suppression of side reactions, particularly enolization. Some esters, which are prone to side reactions, also react readily with Grignard reagents in the presence of cerium chloride to give normal reaction products in reasonable to high yields.

  氯化铈显着增强了格氏试剂向酮中的添加，显着抑制了副反应，尤其是烯醇化。一些易于发生副反应的酯在氯化铈存在下也很容易与格氏试剂反应，以合理到高产率得到正常反应产物。
• Two New Diterpenoids from the Buds of Wikstroemia chamaedaphne
  作者：Jieru Guo、Jinwen Zhang、Penghua Shu、Lingmei Kong、Xincai Hao、Yongbo Xue、Zengwei Luo、Yan Li、Gao Li、Guangmin Yao、Yonghui Zhang

  DOI：10.3390/molecules17066424

  日期：——

  Two new diterpenoids, wikstroelide Q (1) and prostratin Q (5), together with three known diterpenoids, pimelea factors P2 (2), P3 (3), and prostratin (4), and five known lignans, (+)-epipioresinol (6), (+)-isolariciresinol (7), (−)-lariciresinol (8), (+)-epi-sesaminone (9), and prestegane B (10), were isolated from the buds of Wikstroemia chamaedaphne Meissn. Their structures were elucidated by a combination of spectroscopic analyses. Compounds 1–10 were evaluated for their cytotoxicities against HL-60, SMMC-7721, A549, MCF-7, SW480, and BEAS-2B cell lines in vitro.

  两种新二萜类化合物，荨麻草内酯Q（1）和平卧草内酯Q（5），以及三种已知二萜类化合物，松树因子P2（2）、P3（3）和平卧草内酯（4），再加上五种已知木脂素类化合物，（+）-表松脂酚（6）、（+）-异落叶松树脂酚（7）、（−）-落叶松树脂酚（8）、（+）-表芝麻酚酮（9）和prestegane B（10），从荨麻草（Wikstroemia chamaedaphne Meissn）的芽中分离得到。它们的结构通过综合光谱分析得以确定。化合物1至10在体外对HL-60、SMMC-7721、A549、MCF-7、SW480和BEAS-2B细胞系进行了细胞毒性评估。
• Development of a Scalable Lanthanide Halide/Quaternary Ammonium Salt System for the Nucleophilic Addition of Grignard Reagents to Carbonyl Groups and Application to the Synthesis of a Remdesivir Intermediate
  作者：Andrew C. Stevens、Katrien Brak、W. Stacy Bremner、Angela M. Brown、Andrei Chtchemelinine、Lars Heumann、James A. Kerschen、Witold Subotkowski、Tiago Vieira、Lydia C. Wolfe、Boran Xu、Chia-Yun Yu

  DOI：10.1021/acs.oprd.1c00191

  日期：2022.3.18

  implementation of a scalable additive system, consisting of a lanthanide salt and a solubilizing quaternary ammonium salt, to improve the yield and robustness of the addition of an organomagnesium reagent to a ribonolactone en route to remdesivir. This system was found to be generally applicable in enhancing other challenging organomagnesium additions to enolizable and hindered carbonyl-containing compounds

  本手稿描述了可扩展添加剂系统的开发和实施，该系统由镧系元素盐和增溶季铵盐组成，以提高向瑞德西韦添加有机镁试剂到核糖酸内酯的产量和稳定性。发现该系统通常适用于增强其他具有挑战性的有机镁添加到可烯醇化和受阻的含羰基化合物中。