(S)-1-(4-isopropylphenyl)-1-propanol

• 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
• 英文名称: (S)-1-(4-isopropylphenyl)-1-propanol
• 英文别名: (1S)-1-(4-propan-2-ylphenyl)propan-1-ol
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: NUNYALSGVAYXDW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 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

• 作为产物：
  描述：

  diethylzinc 、 4-异丙基苯甲醛 在 [S-(2exo,3exo)]-1,7,7-trimethyl-3-[methyl[(pyridin-3-yl)methyl]amino]bicyclo[2.2.1]heptan-2-ol 、 盐酸 作用下， 以 甲苯 、 水 为溶剂， 以91%的产率得到(S)-1-(4-isopropylphenyl)-1-propanol
  参考文献：
  名称：

  Design, synthesis, and application of novel chiral ONN ligands for asymmetric alkylation

  摘要：

  Starting from easily available chiral pool amino alcohols, a set of novel chiral ONN ligands was synthesized and their catalytic potential was examined in asymmetric alkylation. Ligands with a secondary central NH group and N-methylated ONN ligands were successfully applied as catalysts in the addition of diethyl zinc to various aromatic aldehydes, yielding secondary alcohols in excellent yields of up to 99 % ee.

  DOI：

  10.1007/s00706-012-0900-8

文献信息

• Enantioselective Alkylation of Aldehydes with Diethylzinc Catalyzed by C₂-Symmetric Ligands
  作者：David Williams、Mark Fromhold

  DOI：10.1055/s-1997-6125

  日期：1997.6

  The C2-symmetric pyridine 1, incorporating two units of (-)-ephedrine, is an effective catalyst for the enantioselective reactions of diethylzinc with a series of aromatic aldehydes. The propanol products possess the S-configuration. This result is a significant reversal of stereochemistry based upon literature precendents and our direct comparisons with reactions catalyzed by the corresponding C2-symmetric xylene 2.

  C2对称的吡啶1，包含两个(-)-麻黄碱单元，是二乙基锌与一系列芳香醛的手性选择性反应中有效的催化剂。所得到的丙醇产品具有S配置。这个结果与文献中的前例以及我们与相应的C2对称二甲苯2催化的反应进行直接比较后，展现出了显著的立体化学逆转。
• Enantioselective diethylzinc addition to aldehydes catalyzed by Ti(IV) complex of unsymmetrical chiral bis(sulfonamide) ligands of trans-cyclohexane 1,2-diamine
  作者：Alakesh Bisai、Pradeep K. Singh、Vinod K. Singh

  DOI：10.1016/j.tet.2006.11.022

  日期：2007.1

  Titanium(IV) complexes of bidentate trans-cyclohexane 1,2-diamine-based unsymmetrical chiral bis(sulfonamide) ligands were evaluated as catalysts for the asymmetric addition of diethylzinc to aldehydes. The reaction provided secondary alcohols in quantitative yields and very good enantioselectivity (up to 96% ee).

  评价了基于二齿反式环-环己烷1,2-二胺的不对称手性双（磺酰胺）配体的钛（IV）配合物作为将二乙基锌不对称加成到醛中的催化剂。该反应以定量收率和非常好的对映选择性（高达96％ee）提供了仲醇。
• Synthesis of a Schiff’s base chiral ligand with a trifluoromethyl carbinol moiety
  作者：Yasser Samir Sokeirik、Masaaki Omote、Kazuyuki Sato、Itsumaro Kumadaki、Akira Ando

  DOI：10.1016/j.tetasy.2006.08.023

  日期：2006.10

  A Schiff's base ligand with a trifluoromethyl carbinol moiety was synthesized, and a structure of the active complex for asymmetric induction on the reaction of diethylzinc with aldehydes is proposed. (c) 2006 Published by Elsevier Ltd.
• Design, synthesis, and application of novel chiral ONN ligands for asymmetric alkylation
  作者：Katharina Bica、Sonja Leder、Kurt Mereiter、Peter Gaertner

  DOI：10.1007/s00706-012-0900-8

  日期：2013.4

  Starting from easily available chiral pool amino alcohols, a set of novel chiral ONN ligands was synthesized and their catalytic potential was examined in asymmetric alkylation. Ligands with a secondary central NH group and N-methylated ONN ligands were successfully applied as catalysts in the addition of diethyl zinc to various aromatic aldehydes, yielding secondary alcohols in excellent yields of up to 99 % ee.