meso-1,2,5,6-tetrahydroxyhexane | 20221-50-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: meso-1,2,5,6-tetrahydroxyhexane
• 英文别名: 3,4-dideoxy-D-threo-hexitol；trans-hexane-1,2,5,6-tetrol；meso-Hexantetraol-(1,2,5,6)；meso-hexane-1,2,5,6-tetraol；(2R,5S)-hexane-1,2,5,6-tetrol
• CAS: 20221-50-5
• 化学式: C₆H₁₄O₄
• 分子量: 150.175
• InChiKey: AMXRXGOSEWMPEF-OLQVQODUSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  400.8±40.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  meso-1,2,5,6-tetrahydroxyhexane 、 硫酸 生成 2,5-双[羟甲基]四氢呋喃
  参考文献：
  名称：

  URBAS, BRANKO

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-dideoxy-D-threo-hex-E-3-enitol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以35%的产率得到meso-1,2,5,6-tetrahydroxyhexane
  参考文献：
  名称：

  Synthesis of 1,2:5,6-dianhydro-3,4-dideoxy-erythro- and D-threo-hexitol and their E-3-ENE derivatives

  摘要：

  DOI：

  10.1016/s0008-6215(00)85364-1

文献信息

• Double Asymmetric Dihydroxylation of 1,5-Hexadiene
  作者：Martin E. Maier、Sebastian Reuter

  DOI：10.1002/jlac.199719971006

  日期：1997.10

  Double asymmetric dihydroxylation of 1,5-hexadiene gave in one step a mixture of the d,l/meso tetrols 6 in a ratio of 3.4:1. From this ratio a facial selectivity of 6.65:1 for each double bond can be calculated. As a consequence of the double reaction the d/l ratio can be estimated to be 44:1. Compound 6 served then as starting material for the preparation of the bis-epoxide 12 and the 2,5-dihydroxyhexane

  1，5-己二烯的双不对称二羟基化一步得到d，l /内消旋四元醇6的比例为3.4：1的混合物。根据该比率，可以计算出每个双键的面部选择性为6.65：1。由于双重反应的结果，d / l比可以估计为44：1。然后将化合物6用作制备双环氧化物12和2,5-二羟基己烷（13）的原料。尽管到目前为止还不可能分离非对映异构体，但是这种制备6、12和13的途径 可能仍然有用，因为它很短，并且衍生自它们的产品可能会导致关键分离。
• Aliphatic hydroxy-acids. Part III. Syntheses with alkyl 2-acetoxy-3-carboxypropionates
  作者：R. Brettle、D. W. Latham

  DOI：10.1039/j39680000906

  日期：——

  Methyl (±)-2-acetoxy-3-carboxypropionate has been prepared from (±)-malic acid and used in crossed Kolbe electrolyses to prepare dimethyl (±)-2-acetoxydodecane-1,12-dioate and three methyl 2-acetoxyalkanoates. Dimethyl and diethyl meso-2,5-diacetoxyadipates have been isolated from the Kolbe electrolyses of methyl and ethyl (±)-2-acetoxy-3-carboxypropionates respectively, and the presence of the corresponding

  由（±）-苹果酸制得（±）-2-乙酰氧基-3-羧基丙酸甲酯，并用于交叉Kolbe电解中以制备（±）-2-乙酰氧基十二烷-1,12-二酸二甲酯和3种2-乙酰氧基链烷酸甲酯。 。分别从甲基和（±）-2-乙酰氧基-3-羧基丙酸乙酯的Kolbe电解质中分离了内消旋-2,5-二乙酰氧基己二酸二甲酯和二乙基，相应的（±）-2,5-二乙酰氧基己二酸酯的存在已建立。氢化锂铝将二乙基内消旋-2,5-二乙酰氧基己二酸酯还原得到内消旋-己烷-1,2,5,6-四醇。
• Catalytic production of hexane-1,2,5,6-tetrol from bio-renewable levoglucosanol in water: effect of metal and acid sites on (stereo)-selectivity
  作者：Siddarth H. Krishna、Mario De bruyn、Zachary R. Schmidt、Bert M. Weckhuysen、James A. Dumesic、George W. Huber

  DOI：10.1039/c8gc02455c

  日期：——

  We report on a new route to produce hexane-1,2,5,6-tetrol from cellulose-derived levoglucosanol using metal and acid catalysts.

  我们报道了一种新的方法，使用金属和酸催化剂从纤维素衍生的木糖醇中制备己烷-1,2,5,6-四醇。
• Catalytic production of 1,2,5,6-hexanetetrol from levoglucosenone
  申请人：Wisconsin Alumni Research Foundation

  公开号：US11247956B2

  公开（公告）日：2022-02-15

  A method of making of 1,2,5,6-hexanetetrol (“tetrol”). The method includes the steps of contacting a reaction solution containing water as well as levoglucosenone, dihydrolevoglucosenone, and/or levoglucosanol, with a catalyst containing metal and acid functionalities, at temperature of from about 100° C. to about 175° C., and a hydrogen partial pressure of from about 1 bar to about 50 bar (about 0.1 MPa to about 5 MPa), and for a time wherein at least a portion of the reactant is converted into 1,2,5,6-hexanetetrol.

  一种制造 1,2,5,6-己烷四醇（"四醇"）的方法。该方法包括以下步骤：将含有水以及左旋葡糖酮、二氢左旋葡糖酮和/或左旋葡糖醇的反应溶液与含有金属和酸官能团的催化剂接触，温度约为 100 摄氏度至约 175 摄氏度，氢分压约为 1 巴至约 50 巴（约 0.1 兆帕至约 5 兆帕），反应时间为一段时间，其中至少有一部分反应物转化为 1,2,5,6-己烷四醇。
• NON-IONIC AMPHIPHILES AND METHODS OF MAKING THE SAME
  申请人：Archer Daniels Midland Company

  公开号：US20170233337A1

  公开（公告）日：2017-08-17

  Sugar-derived tetrol, non-ionic amphiphilic amine-esters are prepared facilely and efficaciously in a few steps. The process is initiated by the esterification of a sugar-derived tetrol with a fatty acid chloride, then, undergoing triflate esterification followed by nucleophilic displacement of the aforementioned hydrophilic amine. Each synthetic pathway is efficient and affords modest to high yields of target amphiphiles, which are valorized as practicable surfactant surrogates to petroleum incumbents.