(R)-3-phenyl-1-(p-tolyl)propan-1-ol | 1570511-20-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-3-phenyl-1-(p-tolyl)propan-1-ol
• 英文别名: (1R)-1-(4-methylphenyl)-3-phenylpropan-1-ol
• CAS: 1570511-20-4
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: SJRXWCIQLKCVBX-MRXNPFEDSA-N

物化性质

• 沸点：
  363.1±11.0 °C(predicted)
• 密度：
  1.057±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (R)-4,4,5,5-tetramethyl-2-(3-phenyl-1-(p-tolyl)propyl)-1,3,2-dioxaborolane 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-3-phenyl-1-(p-tolyl)propan-1-ol
  参考文献：
  名称：

  A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates

  摘要：

  Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral B-10-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of configuration at carbon.

  DOI：

  10.1021/ja500029w

文献信息

• Room‐Temperature Guerbet Reaction with Unprecedented Catalytic Efficiency and Enantioselectivity
  作者：Teng Wei Ng、Gang Liao、Kai Kiat Lau、Hui‐Jie Pan、Yu Zhao

  DOI：10.1002/anie.202004758

  日期：2020.7.6

  herein an unprecedented highly efficient Guerbet‐type reaction at room temperature (catalytic TON up to >6000). This β‐alkylation of secondary methyl carbinols with primary alcohols has significant advantage of delivering higher‐order secondary alcohols in an economical, redox‐neutral fashion. In addition, the first enantioselective Guerbet reaction has also been achieved using a commercially available

  我们在此报告了室温下前所未有的高效Guerbet型反应（催化TON高达> 6000）。仲甲基甲醇与伯醇的这种β-烷基化具有显着的优势，即可以经济，氧化还原中性的方式提供高阶仲醇。此外，还使用市售的手性钌配合物实现了第一个对映选择性Guerbet反应，以中等收率和高达92％ee的速率输送仲醇。在两个反应中，使用无痕酮助催化剂均被证明对催化效率有利。
• Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands
  作者：Rui Miao、Yanping Xia、Yifei Wei、Lu Ouyang、Renshi Luo

  DOI：10.3390/molecules27123898

  日期：——

  situ was found to promote an enantioselective addition of aliphatic aldehydes with arylboronic acids, delivering the chiral alcohols in excellent yields and enantioselectivities and exhibiting a broad scope of aliphatic aldehydes and arylboronic acids. The enantioselectivities are highly dependent on the monophosphorous ligands. The utility of this asymmetric synthetic method was showcased by a large-scale

  手性醇在精细化学品、医药和农用化学品中应用最为广泛。在此，发现原位形成的钌-单膦催化剂可促进脂肪醛与芳基硼酸的对映选择性加成，以优异的产率和对映选择性提供手性醇，并表现出广泛的脂肪醛和芳基硼酸范围。对映选择性高度依赖于单磷配体。通过大规模改造展示了这种不对称合成方法的实用性。
• Water-mediated one-pot multi-step synthesis of chiral 1,3-diarylpropan-1-ols by the asymmetric hydrofunctionalisation of simple alkynes
  作者：Pinke Yu、Qixing Liu、Linhong Zuo、Xumu Zhang、Congcong Yin、Haifeng Zhou

  DOI：10.1039/d3gc04945k

  日期：——

  A water-mediated and Rh-catalysed one-pot multi-step synthesis of chiral 1,3-diarylpropan-1-ols is presented. This protocol utilizes readily available terminal alkynes and aldehydes as reaction partners, and features mild conditions, easy operation and water as the sole solvent, thus serving as an ideal means for the efficient synthesis of chiral 1,3-diarylpropan-1-ols. Control experiments suggested

  提出了一种水介导和 Rh 催化的一锅多步合成手性 1,3-二芳基丙-1-醇的方法。该方案利用现成的末端炔烃和醛作为反应伙伴，条件温和，操作简便，以水为唯一溶剂，是高效合成手性1,3-二芳基丙-1-醇的理想手段。对照实验表明，查尔酮中间体的形成以及随后的双还原过程对于反应的成功至关重要。这种催化方法可以很容易地扩大规模，用于高达 10 000 S/C 的克级合成，所得产品可用于轻松衍生各种生物活性分子。
• <i>p</i>-Quinone Methide-Mediated Nonenzymatic Formation of Chalcane-Containing Dimers in Dragon’s Blood
  作者：Ge Liao、Chengneng Mi、Li Yang、Haili Zhang、Xupo Ding、Mingwei Cai、Hao Wang、Wenli Mei、Haofu Dai、Xiaoyu Tang

  DOI：10.1021/acs.orglett.2c03850

  日期：2022.12.23
• A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
  作者：Chunrui Sun、Bowman Potter、James P. Morken

  DOI：10.1021/ja500029w

  日期：2014.5.7

  Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral B-10-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of configuration at carbon.