(R)-(-)-[4-(methoxycarbonyl)phenyl]phenylmethanol

• 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: (R)-(-)-[4-(methoxycarbonyl)phenyl]phenylmethanol
• 英文别名: methyl 4-[(R)-hydroxy(phenyl)methyl]benzoate
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: ZNBIZPXNJOMSFQ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-碘苯甲酸甲酯 、 苯甲醛 在 diethylzinc 、 乙酰基丙酮锂 、 (S)-2-((R)-2-isopropylaziridin-1-yl)-1-phenylethanol 作用下， 以 N-甲基吡咯烷酮 、 四氢呋喃 为溶剂， 反应 13.0h， 以94%的产率得到(R)-(-)-[4-(methoxycarbonyl)phenyl]phenylmethanol
  参考文献：
  名称：

  Highly enantioselective addition of arylzinc reagents to aldehydes promoted by chiral aziridine alcohols

  摘要：

  Enantiomerically pure, chiral secondary and tertiary aziridine alcohols have proven to be highly efficient catalysts for enantioselective asymmetric additions of arylzinc species to aldehydes leading to products in high chemical yields (up to 90%) and with ee's up to 90%. The influence of the stereogenic centers located at the aziridine subunit on the stereochemical course of the reaction is discussed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.10.005

文献信息

• CAMPHOR-DERIVED COMPOUNDS, METHOD FOR MANUFACTURING THE SAME, AND APPLICATION THEREOF
  申请人：UANG Biing-Jiun

  公开号：US20120077976A1

  公开（公告）日：2012-03-29

  Camphor-derived compounds are disclosed, which are represented as the following formula (I): wherein R 1 , R 2 , R 3 , and R 4 each are defined as described in the specification. In addition, a method for manufacturing the camphor-derived compounds and application thereof are disclosed.

  揿脑素衍生化合物的结构如下式（I）所示： 其中R1、R2、R3和R4分别如规范中所述定义。此外，还公开了一种制造揿脑素衍生化合物和应用它们的方法。
• Cobalt-Catalyzed Addition Reaction of Organoboronic Acids with Aldehydes: Highly Enantioselective Synthesis of Diarylmethanols
  作者：Jaganathan Karthikeyan、Masilamani Jeganmohan、Chien-Hong Cheng

  DOI：10.1002/chem.201001160

  日期：——

  Predicted outcomes: The addition reaction of organoboronic acids with aldehydes in the presence of K2CO3 catalyzed by CoI2/(R,R)‐BDPP gives chiral secondary alcohols in excellent yields with 90–99 % enantiomeric excess (see scheme; (R,R)‐BDPP=(2R,4R)‐(+)‐2,4‐bis(diphenylphosphino)pentane). This method provides an alternative to prepare an R and S enantiomeric pair by using the same chiral ligand and

  预期的结果：在CoI 2 /（R，R）-BDPP催化下，在存在K 2 CO 3的情况下，有机硼酸与醛的加成反应可得到出色的手性仲醇，对映体过量90-99％（参见方案；（R，R）-BDPP =（2 R，4 R）-（+）-2,4-双（二苯基膦基）戊烷）。该方法提供了另一种通过使用相同的手性配体制备R和S对映体对的方法，并且可以预测反应的立体化学结果。
• Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand
  作者：Hsyueh-Liang Wu、Ping-Yu Wu、Ying-Ni Cheng、Biing-Jiun Uang

  DOI：10.1016/j.tet.2015.07.038

  日期：2016.5

  synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding

  在本文中，描述了手性樟脑衍生的γ-氨基硫醇配体17的设计和合成，以及通过向羰基化合物中添加有机锌试剂在催化对映选择性碳-碳形成反应中的应用。配体17的催化活性和对映选择性通过将各种有机锌试剂对映选择性加成到醛和酮酯中得到证明，从而以高收率和对映选择性提供相应的醇。还讨论了巯基在有机锌与醛的高度对映选择性1,2加成反应中的作用。
• Synthesis of Planar Chiral [2.2]Paracyclophanyl Imidazo[1,5-<i>a</i>]pyridinium Salts for the Rhodium-Catalyzed Asymmetric Arylation
  作者：Dengxia Wang、Yudao Ma、Fuyan He、Wenzeng Duan、Lei Zhao、Chun Song

  DOI：10.1080/00397911.2011.610548

  日期：2013.2.1

  Abstract Several novel flexibility-restricted imidazo[1,5-a]pyridinium triflates (abbreviated as imidazolium salts) were synthesized from (4S p,13R p)-(−)-4-amino-13-bromo[2.2]paracyclophane and pyridylaldehyde. These imidazolium salts can be used as nitrogen-containing heterocyclic carbene precursors in asymmetric catalysis and here they are applied in the Rh-catalyzed asymmetric 1,2-addition of arylboronic

  摘要 以(4S p,13R p)-(-)-4-氨基-13-溴[2.2]对环芳烷和吡啶醛为原料合成了几种新型柔性受限的咪唑并[1,5-a]吡啶鎓三氟甲磺酸盐（简称咪唑鎓盐）。 . 这些咪唑鎓盐可用作不对称催化中的含氮杂环卡宾前体，在此它们用于 Rh 催化的芳基硼酸与醛的不对称 1,2-加成反应。在优化催化条件和测试一系列底物后，获得了适中的对映选择性和良好的产率。图形概要
• Synthesis of novel planar chiral Ag and Rh N-heterocyclic carbene complexes derived from [2.2]paracyclophane and their application in ultrasound assisted asymmetric addition reactions of organoboronic acids to aldehydes
  作者：Wenzeng Duan、Yudao Ma、Fuyan He、Lei Zhao、Jianqiang Chen、Chun Song

  DOI：10.1016/j.tetasy.2013.01.017

  日期：2013.3

  planar chiral N-heterocyclic carbene silver and rhodium complexes based on [2.2]paracyclophane have been prepared. These could be used as catalysts/precatalysts for the asymmetric 1,2-addition of organoboronic acids to aldehydes. We optimized the reaction conditions and have applied ultrasonic irradiation in the asymmetric arylation for the first time. Under ultrasound irradiation, the combination

  制备了基于[2.2]对环环烷的三种新型平面手性N-杂环卡宾银和铑配合物。这些可以用作有机硼酸向醛的不对称1,2-加成的催化剂/预催化剂。我们优化了反应条件，并首次将超声波辐射应用于不对称芳基化反应中。在超声辐射下，平面手性NHC-Ag配合物5和RhCl 3的组合可以在有机硼酸不对称加成醛中实现更高的催化活性。