meso-α,α'-dihydroxy-1,3-diethylbenzene | 143394-11-0

• 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: meso-α,α'-dihydroxy-1,3-diethylbenzene
• 英文别名: (1R)-1-[3-[(1S)-1-hydroxyethyl]phenyl]ethanol
• CAS: 143394-11-0
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: JXGTYKDVCCARGA-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1,1'-(1,3-phenylene)diethanol 在 sodium acetate 作用下， 以 水 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  间隔式纳米反应器，用于一锅氧化还原驱动的转化

  摘要：

  该贡献引入了基于聚（2-恶唑啉）的壳交联胶束（SCM）作为纳米反应器，以实现在水性介质中对一元醇进行一锅氧化还原驱动的脱硝。TEMPO和Rh-TsDPEN部分分别在空间上位于亲水性电晕和疏水性胶束芯中。TEMPO催化外消旋仲醇氧化成酮，而Rh-TsDPEN催化这些酮的不对称转移氢化（ATH），提供对映体富集的仲醇。Rh-TsDPEN络合物和TEMPO这两种催化剂彼此不相容，并且SCM旨在提供必不可少的催化剂位点隔离。动力学研究表明，SCM可提高固定化催化剂的反应活性，与在相同反应条件下不受支持的类似物相比。我们的纳米反应器可以在多种仲醇底物上进行脱硝反应，并且可以连续的方式重复使用，同时保持较高的活性。

  DOI：

  10.1021/acscatal.8b04667

文献信息

• Dynamic Kinetic Resolution of Secondary Diols via Coupled Ruthenium and Enzyme Catalysis
  作者：B. Anders Persson、Fernando F. Huerta、Jan-E. Bäckvall

  DOI：10.1021/jo990447u

  日期：1999.7.1

  Enzymatic acylation of secondary symmetrical diols (as meso/dl mixtures) in combination with ruthenium-catalyzed isomerization of the diol led to efficient dynamic kinetic resolution. In this way, a meso/dl mixture of the diol was transformed to enantiomerically pure (R,R)-diacetate, making efficient use of all the diol material. For some of the flexible substrates, substantial amounts of meso-diacetates

  二级对称二醇的酶促酰化（作为 meso/dl 混合物）与钌催化的二醇异构化相结合，导致有效的动态动力学拆分。通过这种方式，二醇的内消旋/dl 混合物转化为对映异构纯的 (R,R)-二乙酸酯，从而有效利用所有二醇材料。对于一些柔性基材，大量的内消旋二乙酸盐作为副产物形成。结果表明，内消旋产物的主要部分是通过分子内酰基转移途径形成的。
• Synthesis of chiral phosphine ligands with aromatic backbones and their applications in asymmetric catalysis
  作者：James M. Longmire、Xumu Zhang

  DOI：10.1016/s0040-4039(97)00181-0

  日期：1997.3

  the synthesis of new chiral phosphine ligands has been discovered. A common feature of these ligands is that they contain rigid aromatic backbones which can be used to restrict conformational flexibility. The bite angle of P-M-P can be changed systematically depending on the aromatic backbone. Many asymmetric reactions can potentially be catalyzed by transition metal complexes of these ligands. Moderate

  已经发现了合成新的手性膦配体的一般策略。这些配体的共同特征是它们含有可用于限制构象柔韧性的刚性芳族主链。PMP的咬合角可以根据芳香族骨架进行系统地改变。这些配体的过渡金属络合物可以潜在地催化许多不对称反应。使用这些配体的钯配合物，在1，3-二苯基-2-丙烯基乙酸乙酸酯和丙二酸二甲酯之间的反应中实现了适度的选择性。
• 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.
• US5166062A
  申请人：——

  公开号：US5166062A

  公开（公告）日：1992-11-24