(-)-1-[4-(2,2-dimethylethyl)phenyl]propan-1-ol | 883751-30-2

• 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: (-)-1-[4-(2,2-dimethylethyl)phenyl]propan-1-ol
• 英文别名: (1S)-1-(4-tert-butylphenyl)propan-1-ol
• CAS: 883751-30-2
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: WDEYOAWQRAMQJS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-1-[4-(2,2-dimethylethyl)phenyl]propan-1-ol 在 selenium 、 正丁基锂 、 四甲基乙二胺 、 溴 作用下， 以 正己烷 、 正戊烷 为溶剂， 反应 19.33h， 生成 Trifluoro-methanesulfonate5-tert-butyl-2-((S)-1-hydroxy-propyl)-phenyl-selenonium;
  参考文献：
  名称：

  Asymmetric Addition Reactions with Optimized Selenium Electrophiles

  摘要：

  AbstractThe synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.

  DOI：

  10.1002/chem.19970031123
• 作为产物：
  描述：

  对叔丁基苯甲醛 、 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67%的产率得到(-)-1-[4-(2,2-dimethylethyl)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

• Observation of hyperpositive non‐linear effect in catalytic asymmetric organozinc additions to aldehydes
  作者：Yannick Geiger、Thierry Achard、Aline Maisse‐François、Stéphane Bellemin‐Laponnaz

  DOI：10.1002/chir.23271

  日期：2020.10

  an understanding of how chiral amplification is possible, in particular based on non‐linear effects. Interestingly, it has been proposed a quarter century ago that chiral catalysts, when not enantiopure might even be more enantioselective than their enantiopure counterparts. We show here that such hyperpositive non‐linear effect in asymmetric catalysis is indeed possible. An in‐depth study into the underlying

  不对称扩增是一种现象，据信在生活中出现手性方面起着关键作用。在不对称催化中，已经研究了理论和实验模型，以了解如何进行手性扩增，尤其是基于非线性效应。有趣的是，四分之一世纪前有人提出，手性催化剂在不对映纯的情况下甚至可能比对映纯对映体具有更高的对映选择性。我们在这里表明，这种在非对称催化中的超正非线性效应确实是可能的。进行了对潜在机制的深入研究，我们得出的方案与先前提出的模型不同。
• Functionalized Major-Groove and Minor-Groove Chiral Polybinaphthyls:  Application in the Asymmetric Reaction of Aldehydes with Diethylzinc
  作者：Qiao-Sheng Hu、Wei-Sheng Huang、Dilrukshi Vitharana、Xiao-Fan Zheng、Lin Pu

  DOI：10.1021/ja972623r

  日期：1997.12.1

  have been synthesized by using the Suzuki coupling reaction and have been spectroscopically characterized. The application of these chiral polymers in the asymmetric addition of diethylzinc to aldehydes has been studied. A minor-groove polybinaphthyl is found to be an excellent catalyst for the asymmetric reaction of diethylzinc with a number of aldehydes. The molecular weight and the molecular weight

  通过使用 Suzuki 偶联反应合成了一系列功能化和光学活性的大沟聚联萘和小沟聚联萘，并进行了光谱表征。已经研究了这些手性聚合物在二乙基锌与醛的不对称加成中的应用。发现小槽聚联萘是二乙基锌与许多醛的不对称反应的极好催化剂。聚合物的分子量和分子量分布对催化过程的影响很小。手性聚合物可以很容易地回收和再利用，而不会损失催化活性和对映选择性。这些刚性和空间规则的手性聚联萘代表了新一代的对映选择性聚合催化​​剂。
• Asymmetric Addition Reactions with Optimized Selenium Electrophiles
  作者：Thomas Wirth、Gianfranco Fragale

  DOI：10.1002/chem.19970031123

  日期：1997.11

  AbstractThe synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.
• Chiral Diselenides from Benzylamines: Catalysts in the Diethylzinc Addition to Aldehydes
  作者：Thomas Wirth、Klaus J. Kulicke、Gianfranco Fragale

  DOI：10.1002/hlca.19960790718

  日期：1996.10.30

  synthetic sequence (Scheme 1). Only 1 mol-% of these diselenides catalyzed very effectively the diethylzinc addition to various aromatic and α,β-unsaturated aldehydes yielding the secondary alcohols in up to 98% ee (Scheme 2 and Tables 1 and 2). An asymmetric amplification was observed with these catalysts. Detailed NMR studies were performed to characterize the catalytically active species.

  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。