(R,R)-α,α'-dimethyl-4,4'-biphenylenedimethanol | 15480-49-6

• 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,R)-α,α'-dimethyl-4,4'-biphenylenedimethanol
• 英文别名: 1,1'−([1,1'−biphenyl]−4,4'−diyl)diethanol；(R,R)-1,1'-(biphenyl-4,4'-diyl)diethanol；(1R,1'R)-1,1'-(biphenyl-4,4'-diyl)diethanol；(1R)-1-[4-[4-[(1R)-1-hydroxyethyl]phenyl]phenyl]ethanol
• CAS: 15480-49-6；143329-90-2；143394-13-2；147977-14-8；143329-91-3
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: RANXIKJMWBYSGV-VXGBXAGGSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  412.6±40.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4'-二乙酰联苯 在 (+)-β-chlorodiisopinocampheylborane 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以94%的产率得到(R,R)-α,α'-dimethyl-4,4'-biphenylenedimethanol
  参考文献：
  名称：

  光学纯的有效制备Ç 2通过与不对称还原diacylaromatic化合物-对称芳族二醇乙-chlorodiisopinocampheylborane

  摘要：

  用B-氯二异opinocampheylborane不对称还原二酰基芳烃化合物可提供具有出色的非对映异构和对映异构纯度的产物二醇。

  DOI：

  10.1016/0040-4039(96)00708-3

文献信息

• Asymmetric Synthesis of Biaryl Diols via Dynamic Kinetic Resolution
  作者：Jeonghun Cho、Kyungwoo Kim、Jaiwook Park、Mahn‐Joo Kim

  DOI：10.1002/bkcs.12337

  日期：2021.7

  We have developed a protocol incuding dynamic kinetic resolution as the key step for the asymmetric synthesis of biaryl diol stereoisomers. The two aryl alkanols as the starting materials were cross-coupled by palladium catalysis to give dl- and meso-diol, which were then subject to chemoenzymatic dynamic kinetic resolution (DKR) for the transformation into single stereoisomeric diol diester. Diol

  我们开发了一个协议，包括动态动力学分辨率作为联芳二醇立体异构体不对称合成的关键步骤。两个芳基链烷醇作为起始材料是交叉耦合的由钯催化，得到DL -和内消旋-二醇，然后将其经受化学酶促动态动力学拆分（ DKR）用于转化成单立体异构体的二醇二酯。二醇二酯最终脱酰化得到相应的联芳二醇立体异构体。化学酶促 DKR 使用基于钌的外消旋化催化剂和 ( R ) 选择性脂蛋白脂肪酶进行。总共 17 ( R , R )-二醇，包括 7 C 2合成了具有优异对映纯度 (>99% ee ) 的 -对称二醇。
• Facile assembly of bifunctional, magnetically retrievable mesoporous silica for enantioselective cascade reactions
  作者：Zhongrui Zhao、Fengwei Chang、Tao Wang、Lijian Wang、Lingbo Zhao、Cheng Peng、Guohua Liu

  DOI：10.1039/c9cc07123g

  日期：——

  integrated immobilization to encapsulate the Pd/C-coated magnetic nanoparticles within the chiral Ru/diamine-functionalized silica shell for the construction of a bifunctional magnetic catalyst is developed. This catalyst realizes a synergistic Suzuki cross-coupling/asymmetric transfer hydrogenation and a successive reduction/asymmetric transfer hydrogenation for the preparation of chiral aromatic alcohols

  开发了用于将Pd / C涂覆的磁性纳米颗粒封装在手性Ru /二胺官能化的二氧化硅壳内以用于构建双功能磁性催化剂的集成固定化。该催化剂实现了铃木的交叉偶联/不对称转移加氢的协同作用和连续的还原/不对称转移加氢的制备手性芳族醇。
• An efficient preparation of optically pure C2-symmetric aromatic diols by the asymmetric reduction of diacylaromatic compounds with B-chlorodiisopinocampheylborane
  作者：P.Veeraraghavan Ramachandran、Guang-Ming Chen、Zhi-Hui Lu、Herbert C. Brown

  DOI：10.1016/0040-4039(96)00708-3

  日期：1996.5

  Asymmetric reduction of diacylaromatic compounds with B-chlorodiisopinocampheylborane provides the product diols in excellent diastereomeric and enantiomeric purity.

  用B-氯二异opinocampheylborane不对称还原二酰基芳烃化合物可提供具有出色的非对映异构和对映异构纯度的产物二醇。
• Separation of remote diol and triol stereoisomers by enzyme-catalyzed esterification in organic media or hydrolysis in aqueous media
  作者：J. Shield Wallace、Bruce W. Baldwin、Cary Morrow

  DOI：10.1021/jo00045a042

  日期：1992.9

  The separation of symmetric, remote, secondary diol stereoisomers by steroselective enzyme-catalyzed acetylation with acetic anhydride in anhydrous, low polarity organic solvents or by stereoselective enzyme-catalyzed hydrolysis of the corresponding peracetate in aqueous media is described. Whether or not an alcohol is acetylated or an acetate is hydrolyzed is determined solely by its own stereochemical arrangement and not by the stereochemistry at any other stereogenic center. Since the enzyme used, Amano P lipoprotein lipase from Pseudomonas species, acetylates secondary alcohol stereogenic centers of the (R)-configuration, an (R,R)-diol is converted to its diacetate, a meso-diol is converted to the monoacetate at its (R)-stereogenic center, and an (S,S)-diol is left unchanged. Similarly, when hydrolysis is used, (R)-stereogenic centers are hydrolyzed so that the (R,R)-stereoisomer is converted to the corresponding diol while the (S,S)-stereoisomer remains a diacetate. The resulting mixture is separated, and the remaining acetates are removed by hydrolysis to give diols and triols of high stereochemical purity. Diols successively separated by esterification include alpha,alpha-dimethyl-1,4-benzenedimethanol, 1, alpha,alpha'-dimethyl-1,3-benzenedimethanol, 4, alpha,alpha'-dimethyl-2,6-pyridinedimethanol, 5, and alpha,alpha-dimethyl-4,4-biphenylenedimethanol, 6. For two cases, alpha,alpha'-dimethyl-2,6-pyridinedimethanol, 5, and alpha,alpha',alpha''-trimethyl-1,3,5-benzenetrimethanol, 7, the separation was achieved using the hydrolysis procedure. The stereochemical purity of each of the separated diol stereoisomers was determined by evaluating the NMR spectrum of its bis-MTPA ester. In most cases, it was possible to establish both the stereochemical purity of the fraction and the amount of each contaminating stereoisomer that was present. The diol products are expected to be of value for preparing optically active polymers and optically active crown ethers.
• Varying the ratio of formic acid to triethylamine impacts on asymmetric transfer hydrogenation of ketones
  作者：Xiaowei Zhou、Xiaofeng Wu、Bolun Yang、Jianliang Xiao

  DOI：10.1016/j.molcata.2012.02.002

  日期：2012.5

  Asymmetric transfer hydrogenation (ATH) is frequently carried out in the azeotropic mixture of formic acid (F) and triethylamine (T), where the FIT molar ratio is 2.5. This study shows that the F/T ratio affects both the reduction rate and enantioselectivity, with the optimum ratio being 0.2 ill the ATH of ketones with the Ru-TsDPEN catalyst. Under such conditions, a range of substrates have been reduced, affording high yields and good to excellent enantioselectivities. In comparison with the common azeotropic F-T system, the reduction is faster. This protocol improves both the classic azeotropic and the aqueous-formate system when using water-insoluble ketones. (C) 2012 Elsevier B.V. All rights reserved.