2-tert-butylpropane-1,2,3-triol | 1133797-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-tert-butylpropane-1,2,3-triol
• 英文别名: Mono-t-butylglycerol
• CAS: 1133797-41-7
• 化学式: C₇H₁₆O₃
• 分子量: 148.202
• InChiKey: PGQYJNWAXBIJAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-tert-butylpropane-1,2,3-triol 、 叔丁基二甲基氯硅烷 在 HOVEYDA-SNAPPER去对称化反应催化剂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到(R)-2-((tert-butyldimethylsilyloxy)methyl)-3,3-dimethylbutane-1,2-diol
  参考文献：
  名称：

  无环和环状三醇的催化对映选择性硅烷化：在 Cleroindicins D、F 和 C 全合成中的应用

  摘要：

  从三个中选择一个：无环和环状 1,2,3-三醇被小分子催化剂以优异的位点和对映选择性甲硅烷基化，得到具有相邻二醇部分的甲硅烷基醚。新工艺应用于三种 cleroindicins 的对映选择性全合成，这是一种从中国用于对抗疟疾和风湿病的植物中分离出来的天然产物。

  DOI：

  10.1002/anie.200805338

文献信息

• Enantioselective silyl protection of alcohols promoted by a combination of chiral and achiral Lewis basic catalysts
  作者：Nathan Manville、Hekla Alite、Fredrik Haeffner、Amir H. Hoveyda、Marc L. Snapper

  DOI：10.1038/nchem.1708

  日期：2013.9

  Catalytic enantioselective monosilylations of diols and polyols furnish valuable alcohol-containing molecules in high enantiomeric purity. These transformations, however, require high catalyst loadings (20–30 mol%) and long reaction times (2–5 days). Here, we report that a counterintuitive strategy involving the use of an achiral co-catalyst structurally similar to the chiral catalyst provides an effective solution to this problem. A combination of seemingly competitive Lewis basic molecules can function in concert such that one serves as an achiral nucleophilic promoter and the other performs as a chiral Brønsted base. On the addition of 7.5–20 mol% of a commercially available N-heterocycle (5-ethylthiotetrazole), reactions typically proceed within one hour, and deliver the desired products in high yields and enantiomeric ratios. In some instances, there is no reaction in the absence of the achiral base, yet the presence of the achiral co-catalyst gives rise to facile formation of products in high enantiomeric purity. A counter-intuitive strategy that combines a chiral Lewis base catalyst with an achiral Lewis base co-catalyst results in an exceptionally large increase in the facility of catalytic enantioselective silylation of polyols. The catalytic ensemble drives such reactions to completion within a few hours, rather than the usual two–five days, without loss of enantioselectivity.

  二元醇和多元醇的催化对映体选择性单硅烷化反应可以提供高对映体纯度的有价值含醇分子。然而，这些转化需要较高的催化剂负载量（20-30 摩尔%）和较长的反应时间（2-5 天）。在此，我们报告了一种反直觉策略，即使用结构上与手性催化剂相似的非手性辅助催化剂，从而有效地解决了这一问题。看似相互竞争的路易斯碱分子组合可以协同发挥作用，其中一个作为非手性亲核促进剂，另一个作为手性布氏碱。加入7.5â20Â mol%的市售N-杂环（5-乙基噻四唑）后，反应通常会在一小时内进行，并以较高的产率和对映体比率得到所需的产物。在某些情况下，如果没有非手性碱，则不会发生反应，但如果有非手性辅助催化剂存在，则很容易形成对映体纯度很高的产物。将手性路易斯碱催化剂与非手性路易斯碱助催化剂结合在一起的反直觉策略可显著提高多元醇的对映选择性硅烷化催化效率。这种催化组合可在几小时内完成此类反应，而不是通常的两天到五天，而且不会丧失对映选择性。
• PROCESSES AND SYSTEMS FOR GENERATING GLYCEROL ETHERS THROUGH TRANSETHERIFICATION
  申请人：Saudi Basic Industries Corporation

  公开号：EP3119740A1

  公开（公告）日：2017-01-25
• METHODS FOR PREPARING GLYCEROL TERT-BUTYL ETHERS
  申请人：SABIC Global Technologies B.V.

  公开号：EP3250541A1

  公开（公告）日：2017-12-06
• [EN] PROCESSES AND SYSTEMS FOR GENERATING GLYCEROL ETHERS THROUGH TRANSETHERIFICATION<br/>[FR] PROCÉDÉS ET SYSTÈMES DE PRODUCTION D'ÉTHERS DE GLYCÉROL PAR TRANSÉTHÉRIFICATION
  申请人：SAUDI BASIC IND CORP

  公开号：WO2015140714A1

  公开（公告）日：2015-09-24

  A process of generating a glycerol ether is provided. The process includes reacting isobutylene with an alcohol to obtain a tertiary alkyl ether through an etherification reaction and generating a glycerol ether from the tertiary alkyl ether and glycerol through a transetherification reaction, A system for generating a glycerol ether is also provided.
• [EN] PROCESSES AND SYSTEMS FOR PREPARING GLYCEROL TERT-BUTYL ETHERS FROM GLYCEROL AND ISOBUTYLENE<br/>[FR] PROCÉDÉS ET SYSTÈMES DE PRÉPARATION D'ÉTHERS TERT-BUTYLIQUES DE GLYCÉROL À PARTIR DE GLYCÉROL ET D'ISOBUTYLÈNE
  申请人：SABIC GLOBAL TECHNOLOGIES BV

  公开号：WO2015198268A1

  公开（公告）日：2015-12-30

  A process for generating a glycerol tert-butyl ether is provided. The process includes feeding glycerol and isobutylene into a reactor and reacting glycerol with isobutylene to obtain a glycerol tert-butyl ether through an etherification reaction. The reactor includes an acid catalyst, and the reactor is configured at a temperature and a pressure at which isobutylene is in a gaseous phase and glycerol is in a liquid phase. Additional processes and systems for generating glycerol tert-butyl ethers are also provided.