(1R)-1-(4-异丙基苯基)乙醇 | 105364-42-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (1R)-1-(4-异丙基苯基)乙醇
• 中文别名: 甲基-6-脱氧-2,3-异亚丙基-4-亚甲基来苏-吡喃糖苷
• 英文名称: (R)-1-(4-isopropylphenyl)ethanol
• 英文别名: (1R)-1-(4-isopropylphenyl)ethanol；(1R)-1-(4-propan-2-ylphenyl)ethanol
• CAS: 105364-42-9
• 化学式: C₁₁H₁₆O
• mdl: MFCD09863760
• 分子量: 164.247
• InChiKey: LPWMXVJCBUKVQH-SECBINFHSA-N

物化性质

• 沸点：
  231.2±8.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 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：

  1-(4-isopropylphenyl)ethanol 在 吡啶 、 BES buffer 、 Lipase from Burkholderia cepacia 、 calcium chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 (1R)-1-(4-异丙基苯基)乙醇
  参考文献：
  名称：

  How Substrate Solvation Contributes to the Enantioselectivity of Subtilisin toward Secondary Alcohols

  摘要：

  The current rule to predict the enantiopreference of subtilisin toward secondary alcohols is based on the size of the substituents at the stereocenter and implies that the active site contains two differently sized pockets for these substituents. Several experiments are inconsistent with the current rule. First, the X-ray structures of subtilisin show there is only one pocket (the S1' pocket) approximately the size of a phenyl group to bind secondary alcohols. Second, the rule often predicts the incorrect enantiomer for reactions in water. To resolve these contradictions, we refine the current rule to show that subtilisin binds only one substituent of a secondary alcohol and leaves the other in solvent. To test this refined empirical rule, we show that the enantioselectivity of a series of secondary alcohols in water varied linearly with the difference in hydrophobicity (log P/P0) of the substituents. This hydrophobicity difference accounts for the solvation of one substituent in water.

  DOI：

  10.1021/ja0528937

文献信息

• Iron-catalyzed asymmetric hydrosilylation of ketones
  作者：Ziqing Zuo、Lei Zhang、Xuebing Leng、Zheng Huang

  DOI：10.1039/c5cc00612k

  日期：——

  iminopyridine-oxazoline (IPO) ligands have been synthesized. The most sterically hindered iron catalyst exhibits excellent activity (up to 99% yield) and high enantioselectivity (up to 93% ee) in asymmetric hydrosilylation of aryl ketones.

  已经合成了一系列手性亚氨基吡啶-恶唑啉（IPO）配体的铁配合物。受空间最大阻碍的铁催化剂在芳基酮的不对称氢化硅烷化中表现出出色的活性（高达99％的收率）和高的对映选择性（高达93％ee）。
• Highly Enantioselective Addition of Me₂Zn to Aldehydes Catalyzed by ClCr(Salen)
  作者：Pier Giorgio Cozzi、Peter Kotrusz

  DOI：10.1021/ja057969d

  日期：2006.4.1

  enantiomeric excesses are obtained in the addition of Me2Zn catalyzed by commercially available ClCr(Salen). Broad scope, simple procedure, room temperature, low catalyst loading are the characteristics of this new enantioselective process, which uses the rather unreactive Me2Zn. Enantiomeric excesses in the range of 71-99% are obtained with all the aldehydes tested.

  在由市售的 ClCr(Salen) 催化的 Me2Zn 的添加中获得高对映体过量。范围广、程序简单、室温、催化剂负载量低是这种新的对映选择性工艺的特点，它使用相当不活泼的 Me2Zn。所有测试的醛都获得了 71-99% 范围内的对映体过量。
• Studies on Rhizopus arrhizus mediated enantioselective reduction of arylalkanones
  作者：Neeta A Salvi、Subrata Chattopadhyay

  DOI：10.1016/s0040-4020(01)00134-x

  日期：2001.4

  The effect of substitution on the biotransformation of various arylalkanones using Rhizopus arrhizus was investigated. The organism was found to be promising for the reduction of phenylalkanones and arylethanones with good to excellent enantioselectivity. The reduction followed Prelog's rule giving the (S)-carbinols in all the cases. The enantioselectivity of the reaction improved with increasing size

  研究了使用根霉根对取代对各种芳基链烷酮生物转化的影响。发现该生物有望以良好至优异的对映选择性还原苯基链烷酮和芳酮。在所有情况下，还原均遵循Prelog规则，给出（S）碳氢化合物。反应的对映选择性随羰基官能团侧基的尺寸增加和芳环中取代基的吸电子能力而提高。但是，底物疏水性的提高极大地影响了产率。
• Enantioselective addition of methyl group to aldehydes catalyzed by titanium complex of fluorous ligand
  作者：Masaaki Omote、Naoya Tanaka、Atsushi Tarui、Kazuyuki Sato、Itsumaro Kumadaki、Akira Ando

  DOI：10.1016/j.tetlet.2007.02.130

  日期：2007.4

  Titanium complex of fluorous axially dissymmetric ligand ((Ra∗)-2,2′-bis[(R∗)-perfluoro-1H-1-hydroxyoctyl]biphenyl, ((Ra∗)-(R∗)2-1)) having perfluoroheptyl carbinol moieties catalyzed enantioselective addition of a methyl group to aldehydes. Dimethylzinc prepared in situ by mixing ZnCl2 and methyl magnesium bromide without removal of magnesium salt was more reactive for addition of methyl group than

  钛络合物氟轴向不对称配体（（的ř一个* ）-2,2'-二[（[R * ） -全氟-1- ħ -1-羟]联苯，（（ř一个* ） - （- [R *）2 - 1））具有全氟庚基甲醇部分催化的甲基对醛的对映选择性加成。在不除去镁盐的情况下通过将ZnCl 2和甲基溴化镁混合原位制备的二甲基锌与不具有镁盐的二甲基锌相比，对添加甲基的反应性更高，并给出了99％ee的产物。高氟含量1 使其可以通过全氟己烷的选择性萃取来回收。
• Activity and specificity studies of the new thermostable esterase EstDZ2
  作者：Kamela Myrtollari、Nikolaos Katsoulakis、Dimitra Zarafeta、Ioannis V. Pavlidis、Georgios Skretas、Ioulia Smonou

  DOI：10.1016/j.bioorg.2020.104214

  日期：2020.11

  In this paper, we study the activity and specificity of EstDZ2, a new thermostable carboxyl esterase of unknown function, which was isolated from a metagenome library from a Russian hot spring. The biocatalytic reaction employing EstDZ2 proved to be an efficient method for the hydrolysis of aryl p-, o- or m-substituted esters of butyric acid and esters of secondary alcohols. Docking studies revealed

  在本文中，我们研究了功能未知的新型热稳定羧基酯酶EstDZ2的活性和特异性，该酶是从俄罗斯温泉的一个基因组库中分离出来的。采用EstDZ2生物催化反应被证明是芳基的水解的有效方法p - ，Ö -或米取代丁酸的酯和仲醇的酯。对接研究揭示了导致不同底物活性差异的酶的结构特征。