(S)-1-(3,5-bis(trifluoromethyl)phenyl)propan-1-ol

• 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: (S)-1-(3,5-bis(trifluoromethyl)phenyl)propan-1-ol
• 英文别名: 1-(3,5-bis(trifluoromethyl)phenyl)propan-1-ol；(1S)-1-[3,5-bis(trifluoromethyl)phenyl]propan-1-ol
• 化学式: C₁₁H₁₀F₆O
• 分子量: 272.19
• InChiKey: MBQJJEHEDHLDBO-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 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：
  7

反应信息

• 作为产物：
  描述：

  3,5-双三氟甲基苯甲醛 、 diethylzinc 在 (R,R)-bis[2-(1-pyrrolidin-1-yl-ethyl)phenyl] diselenide 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以90%的产率得到(S)-1-(3,5-bis(trifluoromethyl)phenyl)propan-1-ol
  参考文献：
  名称：

  苄胺的手性二硒化物：乙醛中二乙基锌的催化剂

  摘要：

  通过短的合成序列（方案1）制备了一系列在侧链中具有N原子的新的手性二硒化物。这些二硒化物中只有1 mol％非常有效地催化了二乙基锌与各种芳香族和α，β-不饱和醛的加成反应，从而产生了高达98％ee的仲醇（流程2和表1和表2）。用这些催化剂观察到不对称扩增。进行了详细的NMR研究以表征催化活性物质。

  DOI：

  10.1002/hlca.19960790718

文献信息

• Vasicine as tridentate ligand for enantioselective addition of diethylzinc to aldehydes
  作者：Mushtaq A. Aga、Brijesh Kumar、Abdul Rouf、Bhahwal A. Shah、Subhash C. Taneja

  DOI：10.1016/j.tetlet.2014.03.002

  日期：2014.4

  report of natural l-vasicine as tridentate chiral ligand for the enantioselective addition of diethylzinc to a variety of aliphatic and aromatic aldehydes is described. The ligand generates R-isomer of the secondary alcohols upto 98% ee. The quinazoline structure possibly imparts rigidity to the ligand and hence, consistently high enantioselectivity. The importance of the quinazoline ring was also supported

  描述了天然1- vasicine作为三齿手性配体用于将二乙基锌对映选择地添加到各种脂族和芳族醛中的第一个报道。所述配体产生仲醇的R-异构体，其高达98％ee。喹唑啉结构可能赋予配体刚性，因此，始终如一的高对映选择性。与其他相关配体的反应（部分缺乏结构特征）也支持了喹唑啉环的重要性，从而导致较差的对映选择性。
• 2,2′-Bipyridine-α,α′-trifluoromethyl-diol ligand: synthesis and application in the asymmetric Et₂Zn alkylation of aldehydes
  作者：Samuel Lauzon、Thierry Ollevier

  DOI：10.1039/d1cc04556c

  日期：——

  A chiral 2,2′-bipyridine ligand (1) bearing α,α′-trifluoromethyl-alcohols at 6,6′-positions was designed in five steps affording either the R,R or S,S enantiomer with excellent stereoselectivities, i.e. 97% de, >99% ee and >99.5% de, >99.5% ee, respectively. The key step for reaching high levels of stereoselectivity was demonstrated to be the resolution of the α-CF3-alcohol using (S)-ibuprofen as the

  手性 2,2'-联吡啶配体 ( 1 ) 在 6,6'-位带有 α,α'-三氟甲基-醇，分五步设计，得到具有优异立体选择性的R , R或S , S对映异构体，即97 % de, >99% ee 和 >99.5% de, >99.5% ee。已证明达到高立体选择性的关键步骤是使用 ( S )-布洛芬作为拆分剂拆分α-CF 3 -醇。2,2'-联吡啶-α,α'-CF 3 -二醇配体的初步应用在 Zn II 中得到了强调-催化芳香、杂芳香和脂肪醛的不对称乙基化反应。新开发的配体的协同电子缺陷和空间位阻特性使相应的醇具有良好的收率（高达 99%）和对映选择性（高达 95% ee）。从单晶衍射分析中观察到，2,2'-联吡啶-α,α'-CF 3 -二醇配体的络合产生了不寻常的六配位Zn II。
• (S)-(-)- and (R)-(+)-4-Methyl-2-hydroxymethyl[2]paracyclo-[2](5,8)quinolinophane: Novel N,O-Planar Chiral Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Renzo Ruzziconi、Oriana Piermatti、Giacomo Ricci、Daniele Vinci

  DOI：10.1055/s-2002-25350

  日期：——

  Novel planar chiral N,O-ligands derived from (R)-(+)-and (S)-(-)-2,4-dimethyl[2]paracyclo[2](5,8)quinolinophane were synthesized and employed as catalyst in the enantioselective addition of diethylzinc to aromatic aldehydes. On the basis of the ee values, ranging from 30% to 75%, and the configuration of the obtained 1-phenyl-1-propanols a plausible structure of the transition state for the alkylation

  合成了衍生自 (R)-(+)- 和 (S)-(-)-2,4-二甲基[2] 对环 [2](5,8) 喹啉烷的新型平面手性 N,O-配体并将其用作二乙基锌与芳香醛的对映选择性加成反应的催化剂。根据 ee 值（范围为 30% 至 75%）和所得 1-苯基-1-丙醇的构型，讨论了醛类烷基化过程的过渡态的合理结构。
• Cycloheptyl-fused-PNN-manganese catalyzed asymmetric transfer hydrogenation of ketones
  作者：Zechen Wang、Shuo Zhang、Zhifeng Ma、Libin Li、Xiuli Yan、Qianrong Cao、Yi Su、Ning Ma、Zheng Wang

  DOI：10.1016/j.mcat.2024.114274

  日期：2024.7

  of Mn(I) catalysts containing ferrocene-based chiral PNN tridentate ligands with “aliphatic cyclic” groups is described and tested in the asymmetric transfer hydrogenations of ketones. Various ketones (52 examples), including phenylacetones, phenylpropanones, and heterocyclic substrates could be enantioselectively hydrogenated to the corresponding chiral alcohols with conversions up to 99 % and ee values

  描述了一系列含有二茂铁基手性 PNN 三齿配体和“脂肪族环”基团的 Mn(I) 催化剂，并在酮的不对称转移氢化中进行了测试。各种酮（52 个例子），包括苯丙酮、苯丙酮和杂环底物，可以在温和条件下对映选择性氢化成相应的手性醇，转化率高达 99%，ee 值高达 98%。通过低催化剂负载量 (S/C = 2000) 实现了 860 的高周转数。 DFT 计算和控制实验强调了催化剂中远程极性基团 (C = O) 和环庚基的重要性，导致活性增强和对映体过量（高达 98 % ee），并揭示了在有吸引力的芳香族化合物的帮助下的立体控制催化过程中苯基和配体吡啶环之间的π-π堆积相互作用。分析了催化循环中涉及的潜在锰中间体。值得注意的是，该催化方案在温和条件下运行，采用低催化剂负载，并显示出在手性醇药效团的有效合成中的潜在应用。
• ([2]Paracyclo[2](5,8)quinolinophan-2-yl)carbinols as catalysts for diethylzinc addition to aldehydes: cooperative effects of planar and central chirality on the asymmetric induction
  作者：Giacomo Ricci、Renzo Ruzziconi

  DOI：10.1016/j.tetasy.2005.04.003

  日期：2005.5

  A systematic study to assess the contribution of planar and central chirality to the asymmetric induction in the diethylzinc addition to aromatic and aliphatic aldehydes has been carried out using planar chiral quinolinophanylcarbinols (R-p)-1 and (R-p)-11 and diastereomeric quinolinophanylcarbinols (R-p,R)- and (R-p,S)-5-8, exhibiting both planar and central chirality Lis catalysts. The stereochemistry of the addition process leading to aryl- or 1-alkylpropanols seems to be mostly controlled by the central chirality. Nevertheless, the planar chirality shows a remarkable cooperative effect oil the degree of asymmetric induction, which turns Out to be positive or negative depending oil the configuration of the stereogenic carbon of the catalyst. (C) 2005 Elsevier Ltd. All rights reserved.