(S,S,S)-α,α',α''-trimethyl-1,3,5-benzenetrimethanol

• 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: (S,S,S)-α,α',α''-trimethyl-1,3,5-benzenetrimethanol
• 英文别名: (1S,1'S,1''S)-1,1',1''-(benzene-1,3,5-triyl)triethanol；(S,S,S)-1,3,5-tris(1-hydroxyethyl)benzene；(1S)-1-[3,5-bis[(1S)-1-hydroxyethyl]phenyl]ethanol
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: UAHZWJCHJDIXSX-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三乙酰基苯 在 C₃₀H₃₂ClN₂O₂RuS 、 氢气 、 potassium hydroxide 作用下， 以 2,2,2-三氟乙醇 为溶剂， 40.0 ℃ 、4.05 MPa 条件下， 反应 24.0h， 以91%的产率得到(S,S,S)-α,α',α''-trimethyl-1,3,5-benzenetrimethanol
  参考文献：
  名称：

  TfOH催化水合和Ru催化串联不对称加氢将炔烃转化为手性醇

  摘要：

  开发了一种在简单条件下通过TfOH催化水合再加上Ru催化串联T对称不对称氢化将炔烃转化为手性醇的新型全原子经济方法。获得了具有广泛的官能团耐受性，良好的产率和优异的立体选择性的一系列手性醇。

  DOI：

  10.1021/acs.orglett.8b00034

文献信息

• 一种多取代手性(1-羟乙基)苯及其不对称合 成方法
  申请人：三峡大学

  公开号：CN108046995B

  公开（公告）日：2021-06-29

  本发明涉及一种多取代手性(1‑羟乙基)苯，具体结构如II所示，同时本发明公开了该化合物一种“两步一锅法”的合成方法。该方法以廉价易得的多乙炔基取代的苯(I)为原料，经过步骤1)：以含氟的醇和水为溶剂，在三氟甲烷磺酸催化下发生水合反应生成中间体酮；步骤2)：直接在反应体系中加入单磺酰手性二胺与金属钌或铑或铱的配合物为催化剂，并加入碱，充入氢气，不对称氢化反应得到产物II，或者直接在反应体系中加入单磺酰手性二胺与金属钌或铑或铱的配合物为催化剂，甲酸钠或甲酸与三乙胺的混合物为氢源，经不对称转移氢化反应得到产物II。该方法操作简便，原料易得、对映选择性和非对映选择性都很高。
• 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.
• Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation
  作者：Sensheng Liu、Huan Liu、Haifeng Zhou、Qixing Liu、Jinliang Lv

  DOI：10.1021/acs.orglett.8b00034

  日期：2018.2.16

  A novel full atom-economic process for the transformation of alkynes into chiral alcohols by TfOH-catalyzed hydration coupled with Ru-catalyzed tandem asymmetric hydrogenation in TFE under simple conditions has been developed. A range of chiral alcohols was obtained with broad functional group tolerance, good yields, and excellent stereoselectivities.

  开发了一种在简单条件下通过TfOH催化水合再加上Ru催化串联T对称不对称氢化将炔烃转化为手性醇的新型全原子经济方法。获得了具有广泛的官能团耐受性，良好的产率和优异的立体选择性的一系列手性醇。