己烷-2,3-二醇 | 617-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 己烷-2,3-二醇
• 英文名称: 2,3-hexanediol
• 英文别名: hexane-2,3-diol
• CAS: 617-30-1
• 化学式: C₆H₁₄O₂
• 分子量: 118.176
• InChiKey: QCIYAEYRVFUFAP-UHFFFAOYSA-N

物化性质

• 熔点：
  60°C
• 沸点：
  221.7°C (rough estimate)
• 密度：
  0.9900
• 保留指数：
  906

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  己烷-2,3-二醇 在 N-heterocyclic carbene-iridium(III) complex 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 24.0h， 以70%的产率得到2.5-二甲基四氢呋喃
  参考文献：
  名称：

  双功能铱配合物催化二醇环脱水的非经典机理。

  摘要：

  1,4-和1,5-二醇在用阳离子N-杂环卡宾(NHC)-Ir III络合物处理后发生环化脱水，分别生成四氢呋喃和四氢吡喃。研究了该机制，并提出了一种适用于所有底物的金属氢化物驱动途径，除了电子非常丰富的底物。这与涉及亲核取代的成熟经典途径形成对比。

  DOI：

  10.1002/chem.201805460
• 作为产物：
  描述：

  反-2-已烯 在 1,2-dimethyl-1,2-dihydroxiciclohexene-osmium trioxide 、 silica gel 水 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 48.0h， 生成 己烷-2,3-二醇
  参考文献：
  名称：

  A Heterogeneous cis-Dihydroxylation Catalyst with Stable, Site-Isolated Osmium-Diolate Reaction Centers

  摘要：

  Involatile OsO4 ! A tetrasubstituted olefin is immobilized on SiO2 and reacts with OsO4 to form a stable osmate(IV) ester, which is a leak-proof heterogeneous catalyst for the cis-dihydroxylation of olefins.

  DOI：

  10.1002/1521-3773(20010202)40:3<586::aid-anie586>3.0.co;2-l

文献信息

• Chromium-Catalyzed Production of Diols From Olefins
  申请人：Chevron Phillips Chemical Company LP

  公开号：US20210078926A1

  公开（公告）日：2021-03-18

  Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

  将烯烃反应物转化为二醇化合物的过程被披露，这些过程包括以下步骤：接触烯烃反应物和含有六价铬氧化态铬的支持铬催化剂，以还原至少部分支持的铬催化剂以形成还原铬催化剂，并水解还原铬催化剂以形成包含二醇化合物的反应产物。在接触时，烯烃反应物和支持的铬催化剂可以被紫外可见光谱范围内的波长的光束照射。可选地，这些过程还可以包括对至少部分还原铬催化剂进行焙烧的步骤，以再生支持的铬催化剂。
• [EN] SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES BICYCLIQUES SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE PRMT5
  申请人：LUPIN LTD

  公开号：WO2019116302A1

  公开（公告）日：2019-06-20

  The invention relates to substituted bicyclic heterocyclic compounds of formula (I), pharmaceutically acceptable salts thereof and pharmaceutical compositions for treating diseases, disorders or conditions associated with the overexpression of PRMT5 5 enzyme. The invention also relates to methods of treating diseases, disorders or conditions associated with the overexpression of PRMT5 enzyme.

  这项发明涉及公式（I）的取代双环杂环化合物，其药学上可接受的盐以及用于治疗与PRMT5 5酶过度表达相关的疾病、紊乱或状况的药物组合物。该发明还涉及治疗与PRMT5酶过度表达相关的疾病、紊乱或状况的方法。
• Synthesis of aggregation pheromone components of cerambycid species through α-hydroxylation of alkylketones
  作者：Viviana Heguaburu、Hugo do Carmo、Florencia Parpal、María Eugenia Amorós、Andrés González

  DOI：10.1016/j.tetlet.2017.03.053

  日期：2017.5

  The synthesis of 3-hydroxy-2-hexanone and 2,3-hexanediol, two components of the aggregation pheromone of several cerambycid species, is disclosed in here. Starting from 2-hexanone, through an α-hydroxylation using (diacetoxyiodo)benzene, 3-hydroxy-2-hexanone is obtained in good yield. Further reduction of this compound, gives 2,3-hexanediol in excellent yield. A study of the α-hydroxylation reaction

  在此公开了几种羟百菌灵的聚集信息素的两个组分3-羟基-2-己酮和2，3-己二醇的合成。从2-己酮开始，通过使用（二乙酰氧基碘）苯的α-羟基化，以良好的产率获得了3-羟基-2-己酮。进一步还原该化合物，以优异的产率得到2，3-己二醇。本文还公开了使用高价碘试剂对几种烷基酮的α-羟基化反应的研究。光学活性化合物（R）-和（S）-3-羟基-2-己酮的合成是从2-己酮分别与亚硝基苯和1-和d-脯氨酸在几种反应介质中开始进行的。
• Heteroaroyl-Substituted Serine Amides
  申请人：Witschel Matthias

  公开号：US20100099568A1

  公开（公告）日：2010-04-22

  The present invention relates to heteroaroyl-substituted serinamides of the formula (I) in which the variables A and R 1 to R 6 are as defined in the description, and to their agriculturally useful salts, to processes and intermediates for their preparation, and to the use of these compounds or of the compositions comprising these compounds for controlling unwanted plants.

  本发明涉及异芳酰基取代的丝氨酰胺的化学式(I)，其中变量A和R1至R6如描述中所定义，并涉及它们在农业上有用的盐，用于它们的制备过程和中间体，以及利用这些化合物或包含这些化合物的组合物来控制不受欢迎的植物。
• Highly efficient and stereoselective biosynthesis of (2S,5S)-hexanediol with a dehydrogenase from Saccharomyces cerevisiae
  作者：Marion Müller、Michael Katzberg、Martin Bertau、Werner Hummel

  DOI：10.1039/b920869k

  日期：——

  The enantiopure (2S,5S)-hexanediol serves as a versatile building block for the production of various fine chemicals and pharmaceuticals. For industrial and commercial scale, the diol is currently obtained through bakers’ yeast-mediated reduction of 2,5-hexanedione. However, this process suffers from its insufficient space-time yield of about 4 g L−1 d−1 (2S,5S)-hexanediol. Thus, a new synthesis route is required that allows for higher volumetric productivity. For this reason, the enzyme which is responsible for 2,5-hexanedione reduction in bakers’ yeast was identified after purification to homogeneity and subsequent MALDI-TOF mass spectroscopy analysis. As a result, the dehydrogenase Gre2p was shown to be responsible for the majority of the diketone reduction, by comparison to a Gre2p deletion strain lacking activity towards 2,5-hexanedione. Bioreduction using the recombinant enzyme afforded the (2S,5S)-hexanediol with >99% conversion yield and in >99.9% de and ee. Moreover, the diol was obtained with an unsurpassed high volumetric productivity of 70 g L−1 d−1 (2S,5S)-hexanediol. Michaelis–Menten kinetic studies have shown that Gre2p is capable of catalysing both the reduction of 2,5-hexanedione as well as the oxidation of (2S,5S)-hexanediol, but the catalytic efficiency of the reduction is three times higher. Furthermore, the enzyme's ability to reduce other keto-compounds, including further diketones, was studied, revealing that the application can be extended to α-diketones and aldehydes.

  高光学纯度(2S,5S)-己二醇作为一种多用途的构建单元，可用于生产各种精细化学品和药物。在工业和商业规模上，目前通过面包酵母介导的2,5-己二酮还原反应制备该二醇。然而，这一过程存在空间时间产率不足的问题，约为每天每升4克(2S,5S)-己二醇。因此，需要开发一种新的合成路线，以实现更高的体积生产率。为此，通过纯化至均一性并随后进行MALDI-TOF质谱分析，鉴定了面包酵母中负责2,5-己二酮还原的酶。结果显示，与缺乏对2,5-己二酮活性的Gre2p缺失株相比，脱氢酶Gre2p主要负责该二酮的还原。利用重组酶进行生物还原，可获得转化率>99%且对映体过量>99.9%的(2S,5S)-己二醇。此外，该二醇的体积生产率达到了前所未有的70 g L−1 d−1 (2S,5S)-己二醇。米氏动力学研究表明，Gre2p能够催化2,5-己二酮的还原和(2S,5S)-己二醇的氧化，但还原的催化效率高出三倍。此外，研究了该酶对其他酮类化合物（包括更多的二酮）的还原能力，发现其应用可扩展到α-二酮和醛。