(R)-2-methyl-1-(4-methylphenyl)-1-propanol

• 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: (R)-2-methyl-1-(4-methylphenyl)-1-propanol
• 英文别名: (R)-2-methyl-1-(p-tolyl)propanol；(R)-2-methyl-1-(p-tolyl)propan-1-ol；2-methyl-1-(p-tolyl)propan-1-ol；(R)-2-methyl-1-(4-methylphenyl)propanol；(1R)-2-methyl-1-(4-methylphenyl)propan-1-ol
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: PKSSQQPDFFZHEU-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4'-二甲基苯丙酮 在 dimethyl sulfide borane 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(R)-2-methyl-1-(4-methylphenyl)-1-propanol
  参考文献：
  名称：

  Experimental transition state for the B-chlorodiisopinocampheylborane (DIP-Cl) reduction

  摘要：

  Asymmetric reductions of prochiral ketones are important transformations in the syntheses of natural products, pharmaceuticals, and fine chemicals. B-Chlorodiisopinocampheylborane (DIP-Cl), a stoichiometric reagent that is capable of reducing prochiral aralkyl ketones with high selectivity. Here, we utilize a recently developed C-13 kinetic isotope effect (KIE) methodology to probe the symmetry breaking process inherent to this asymmetric reduction. Experimental KIEs and computed transition structures indicate significant roles for non-bonding interaction, specific directed orbital interactions, and hydrogen tunneling in this reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.216

文献信息

• Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand
  作者：Fei Ling、Jiachen Chen、Sanfei Nian、Huacui Hou、Xiao Yi、Feifei Wu、Min Xu、Weihui Zhong

  DOI：10.1055/s-0039-1690783

  日期：2020.2

  A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable ‘side arm’ groups have been established, enabling the inexpensive base-promoted asymmetric hydrogenation of simple ketones with outstanding activities (up to 8200 TON) and good enantioselectivities (up to 88.5% ee). This protocol features wide substrate scope and functional group tolerance, thereby

  已经建立了一系列含有咪唑基手性 PNN 三齿配体和可控“侧臂”基团的 Mn(I) 催化剂，使具有出色活性（高达 8200 TON）和良好对映选择性的简单酮的廉价碱促进不对称氢化成为可能（高达 88.5% ee）。该协议具有广泛的底物范围和官能团耐受性，从而可以轻松获得克唑替尼的关键中间体。
• Highly Enantioselective Addition of Dialkylzincs to Aromatic Aldehydes Using 1-Phenyl-2-(1-pyrrolidinyl)-1-propanol as a Chiral Catalyst
  作者：Kenso Soai、Takashi Konishi、Takanori Shibata

  DOI：10.3987/com-99-8532

  日期：——

  (1S,2R)- and (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol catalyzes the enantioselective addition of dialkylzincs to aromatic aldehydes to afford enantiomerically enriched aromatic sec-alcohols with up to 92% enantiomeric excess.

  (1S,2R)-和(1R,2S)-1-苯基-2-(1-吡咯烷基)-1-丙醇能够催化二烷基锌与芳香醛之间的对映选择性加成反应，生成具有高达92%对映体过量的芳族仲醇。
• Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes
  作者：Itaru Sato、Takanori Shibata、Koji Ohtake、Ryo Kodaka、Yutaka Hirokawa、Nobuaki Shirai、Kenso Soai

  DOI：10.1016/s0040-4039(00)00365-8

  日期：2000.4

  Chiral dendrimers with three or six β-amino alcohols on hyperbranched hydrocarbon chain-ends were synthesized. These macromolecules can act as chiral catalysts for the enantioselective addition of dialkylzincs to aldehydes. The corresponding secondary alcohols are obtained in high enantiomeric excess (up to 86% e.e.).

  合成了在超支链烃链末端具有三个或六个β-氨基醇的手性树状聚合物。这些大分子可以用作手性催化剂，用于将二烷基锌对映体选择性地加成成醛。以高对映异构体过量（至多86％ee）获得相应的仲醇。
• Facile synthesis of chiral isopropyl carbinols with high enantiomeric excess via catalytic enantioselective addition of diisopropylzinc to aldehydes
  作者：Weon Ki Yang、Byung Tae Cho

  DOI：10.1016/s0957-4166(00)00253-6

  日期：2000.7

  Highly effective syntheses of chiral alkyl and aryl isopropyl carbinols with high enantiomeric excess (94–98% ee) via catalytic enantioselective addition of diisopropylzinc to aldehydes have been developed.

  已开发出通过将二异丙基锌催化对映选择性加成到醛中的方法，以高对映体过量（94-98％ee）的方式合成手性烷基和芳基异丙基甲醇。
• Linear β-amino alcohol catalyst anchored on functionalized magnetite nanoparticles for enantioselective addition of dialkylzinc to aromatic aldehydes
  作者：Carla Sappino、Ludovica Primitivo、Martina De Angelis、Francesco Righi、Federica Di Pietro、Marika Iannoni、Luciano Pilloni、Stefano Vecchio Ciprioti、Lorenza Suber、Alessandra Ricelli、Giuliana Righi

  DOI：10.1039/d0ra04554c

  日期：——

  A linear β-amino alcohol ligand, previously found to be a very efficient catalyst for enantioselective addition of dialkylzinc to aromatic aldehydes, has been anchored on differently functionalized superparamagnetic core–shell magnetite–silica nanoparticles (1a and 1b). Its catalytic activity in the addition of dialkylzinc to aldehydes has been evaluated, leading to promising results, especially in

  一种线性 β-氨基醇配体，之前被发现是一种非常有效的催化剂，可以将二烷基锌对映选择性加成到芳香醛上，它已被锚定在不同功能化的超顺磁性核-壳磁铁矿-二氧化硅纳米粒子上（1a和1b）。已经评估了其将二烷基锌添加到醛中的催化活性，取得了可喜的结果，特别是在1b的情况下，通过简单的磁倾析和再利用成功地验证了其回收率。