(4-isopropylphenyl)(phenyl)methanol | 1013121-18-0

• 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: (4-isopropylphenyl)(phenyl)methanol
• 英文别名: (S)-phenyl-(4-propan-2-ylphenyl)methanol
• CAS: 1013121-18-0
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: CTWXUEKUQXNHKY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-异丙基苯甲醛 、 苯硼酸 在 diethylzinc 、 N,N'-trimethylenedi<(S)-diphenyl(pyrrolidin-2-yl)methanol> 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 甲苯 、 苯 为溶剂， 反应 36.0h， 以60%的产率得到(4-isopropylphenyl)(phenyl)methanol
  参考文献：
  名称：

  等规设计的手性催化剂：原理，优化及其在醛的对映选择性亲核加成中的应用

  摘要：

  基于脯氨酸的方法设计了基于脯氨酸的N，N'-二氧化物配体，并将其成功应用于醛的对映选择性亲核加成反应。在10mol％的手性配体1b的存在下，将二乙基锌对映选择性地添加到醛中，以高达90％的分离产率和高达99％的ee提供了相应的仲醇。类似地，使用3e作为手性配体，醛的对映选择性芳基化和炔基化也很容易进行，从而得到所需的手性醇，分别以99％ee和80％分离产率以及84％ee分离率高达92％。当前的工作将有助于扩大手性配体和手性催化剂设计中的结构多样性。

  DOI：

  10.1016/j.tet.2020.131648

文献信息

• Enantioselective Synthesis of Bicyclopentane-Containing Alcohols via Asymmetric Transfer Hydrogenation
  作者：Vijyesh K. Vyas、Guy J. Clarkson、Martin Wills

  DOI：10.1021/acs.orglett.1c00889

  日期：2021.4.16

  1.1]pentane (BCP) adjacent to a chiral center can be prepared with high enantiomeric excess through asymmetric transfer hydrogenation (ATH) of adjacent ketones. In the reduction step, the BCP occupies the position distant from the η6-arene of the catalyst. The reduction was applied to the synthesis of a BCP analogue of the antihistamine drug neobenodine.

  可以通过相邻酮的不对称转移氢化（ATH），以高对映体过量的方式制备与手性中心相邻的含有双环[1.1.1]戊烷（BCP）的化合物。在还原步骤中，将BCP占据远离η位置6的催化剂的-arene。该还原反应用于合成抗组胺药新贝诺定的BCP类似物。
• Bio-inspired asymmetric aldehyde arylations catalyzed by rhodium-cyclodextrin self-inclusion complexes
  作者：Susumu Tsuda、Kaoru Asahi、Ryota Takahashi、Hiroki Yamauchi、Ryoji Ueda、Takanori Iwasaki、Shin-ichi Fujiwara、Nobuaki Kambe

  DOI：10.1039/d1ob02014e

  日期：——

  conditions, with enantiomeric excesses of up to 96% observed. Kinetic and competition experiments revealed that self-inclusion of the Rh complex contributes to the high enantioselectivity and reactivity achieved by this catalytic system. Thus, this bio-inspired self-inclusion strategy is promising for the development of highly enantioselective and reactive transition-metal catalysts for asymmetric carbon–carbon

  过渡金属催化剂是碳-碳键形成反应的有力工具，使用天然酶难以实现。通过主客体相互作用表现出固有选择性和反应性的酶激发了人们对将酶促行为纳入高效生产对映体纯化合物的过渡金属催化系统的广泛兴趣。然而，很少报道具有高度对映选择性和反应性的仿生过渡金属催化剂。在这项研究中，我们将 γ-环糊精-咪唑鎓盐应用于铑催化的醛的不对称芳基化。该方法表现出广泛的底物范围，并且在优化的条件下以优异的产率获得了相应的芳基甲醇，观察到对映体过量高达 96%。动力学和竞争实验表明，Rh 复合物的自包含有助于该催化系统实现的高对映选择性和反应性。因此，这种受生物启发的自包含策略有望用于开发用于不对称碳-碳键形成的高对映选择性和反应性过渡金属催化剂。
• Ag-Catalyzed Stereoselective Cyclohexadienyl Transfer:  A Novel Entry into Arylphenylmethanols
  作者：Rui Umeda、Armido Studer

  DOI：10.1021/ol703080a

  日期：2008.3.1

  The letter describes a novel concept for the synthesis of biologically important arylphenylmethanols. Stereoselective cyclohexadienyl transfer from 1,4-cyclohexadienyltributyltin to various aromatic aldehydes using AgOTf/BINAP as a catalyst precursor provides 1,4-cyclohexadienylphenylmethanols that are readily oxidized to the corresponding arylphenylmethanols. Fifteen examples are presented.
• Chelating alkoxy NHC–Rh(I) complexes and their applications in the arylation of aldehydes
  作者：Serpil Denizaltı、Hayati Türkmen、Bekir Çetinkaya

  DOI：10.1016/j.tetlet.2014.05.125

  日期：2014.7

  In this study, new rhodium(I) complexes (5 and 6) have been prepared by the reaction of [RhCI(COD)](2) with a series of imidazolium salts (3 and 4), which were obtained from a chiral amino alcohol. The catalytic activities of these complexes were tested in the arylation of aldehydes. It was found that the synthesized rhodium complexes were highly effective catalysts for the arylation of aldehydes in short reaction times (5 mm, TOF = 1193 h(-1)). However, the obtained ee values (up to 32% ee) remained low. We have proposed a mechanism for the arylation reaction of aldehydes, which is confirmed via F-19 NMR spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.
• Novel Axially Chiral Phosphine Ligand with a Fluoro Alcohol Moiety for Rh-Catalyzed Asymmetric Arylation of Aromatic Aldehydes
  作者：Satoshi Morikawa、Kyosuke Michigami、Hideki Amii

  DOI：10.1021/ol100697a

  日期：2010.6.4

  A new chiral phosphine ligand (R)-1 possessing a fluoroalcohol moiety was prepared. The (R)-1-coordinated Rh(I) complex showed an excellent catalytic activity for asymmetric 1,2-addition of arylboronic acids to aldehydes to afford highly enantioenriched diarylmethanols. The fluoroalcohol moiety in ligand (R)-1 plays a pivotal role for the high enantioselectivity of the present Rh(I)-catalyzed transformation.