十二烷-6,7-二醇 | 91635-53-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 十二烷-6,7-二醇
• 英文名称: dodecane-6,7-diol
• 英文别名: 6,7-Dodecanediol；meso-Dodecan-6,7-diol；rac.-Dodecan-6,7-diol
• CAS: 91635-53-9
• 化学式: C₁₂H₂₆O₂
• 分子量: 202.337
• InChiKey: RTJLDNBCNXKTTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  9
• 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：

  十二烷-6,7-二醇 在 4-hydroxy-TEMPO benzoate 、 sodium bromide 作用下， 以 二氯甲烷 、 水 为溶剂， 以85%的产率得到十二烷-6,7-二酮
  参考文献：
  名称：

  Indirect electrooxidation of alcohols by a double mediatory system with two redox couples of [R2N+:O]/R2NO.cntdot. and [Br.cntdot. or Br+]/Br- in an organic-aqueous two-phase solution

  摘要：

  An indirect electrooxidation method for alcohol to aldehyde or ketone conversion has been developed. This method, applicable to chemoselective oxidation, employs two redox couples, consisting of 2,2,6,6-tetramethyl-piperidine-1-oxyl derivatives 6 and active bromine species. The former is required for the chemical process and recycled, whereas the latter is to be involved in the electrochemical process. Three chemical events play an important role in this system: (1) the formation of [Br or Br+] from bromide ion by discharge on the anode in an aqueous solution, (2) the reaction of N-oxyl compounds 6 with active bromine species to generate N-oxoammonium ion 7, and (3) the oxidation of alcohols with 7 in an organic phase. Optimum conditions were established as follows: an aqueous 25% NaBr solution buffered at pH 8.6 in a binary system, the use of 1-10 mol % of 4-(benzoyloxy)piperidine derivatives 6, and adjustment of an electric current at 10-100 mA/cm2. The successful applications of the present method to the oxidation of a variety of primary and secondary alcohols including 1,n-diols, giving the corresponding carbonyl compounds, have delineated its synthetic utility. The chemoselective oxidation of a primary hydroxy group in the presence of secondary one has been achieved with a high selectivity by the present procedure.

  DOI：

  10.1021/jo00007a031
• 作为产物：
  描述：

  正己醇 在 sodium hypochlorite 、 3',3',4',4',5',5',6',6',7',7',8',8',8'-tridecafluorooctanoic acid (1-hydroxyl-2,2,6,6-tetramethylpiperidin-4-yl)-(3",3",4",4",5",5",6",6",7",7",8",8",8"-tridecafluorooctyl)-amide 、 碳酸氢钠 、 potassium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以91%的产率得到十二烷-6,7-二醇
  参考文献：
  名称：

  Light-fluorous TEMPO: reagent, spin trap and stable free radical

  摘要：

  The synthesis of two light-fluorous TEMPO derivatives is reported, along with their fluorous-organic solvent partition coefficients and their ESR spectra. Applications of the fluorous-TEMPO reagents in oxidation reactions and as radical traps are discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.078

文献信息

• Oxidation of alcohols with nitroxyl radical under polymer-supported two-phase conditions
  作者：Yoshitomo Kashiwagi、Shinya Chiba、Jun-ichi Anzai

  DOI：10.1039/b307190c

  日期：——

  The oxidation of alcohols to carbonyl compounds was studied using potassium hexacyanoferrate(III) mediated by nitroxyl radical as the catalyst under polymer-supported organic–aqueous two-phase conditions. Primary alcohols are readily oxidized to the corresponding aldehydes in excellent yield with no over-oxidation to carboxylic acids. Secondary alcohols are converted to the corresponding ketones with

  这 氧化作用 的 酒类 到 羰基化合物 被研究使用 六氰合铁酸钾（III） 由...介导 亚硝酰 激进的 催化剂 在下面 聚合物支持的有机-水两相条件。 伯醇 容易被氧化成相应的 醛类 产量极高，不会过度氧化作用 到 羧酸。 仲醇 转换为相应的 酮类效率要低得多。的氧化反应伯醇 在......的存在下 仲醇受到强烈青睐。小学-中学二醇类 被选择性地转化为羟基醛与少量 酮醛，剩余的异构酮醇的量少于1％。
• Organocerium reagents from iodine activated cerium metal and organic iodides: Their reactions with carbonyl compounds
  作者：Shin-Ichi Fukuzawa、Tatsuo Fujinami、Shizuyoshi Sakai

  DOI：10.1016/0022-328x(86)82013-7

  日期：1986.1

  Cerium metal activated by a trace of iodine reacted smoothly with alkyl, allyl, and aryl iodides to give the corresponding organocerium reagents. The reaction of the organocerium reagents thus prepared in situ with carbonyl compounds gave not only Grignard-type adducts but also reduction and reductive coupling products.

  微量碘活化的铈金属与烷基，烯丙基和芳基碘能顺利反应，生成相应的有机铈试剂。由此原位制备的有机铈试剂与羰基化合物的反应不仅得到格利雅（Grignard）型加合物，而且还得到还原和还原偶联产物。
• Diastereoselective synthesis of trans-3,5-disubstituted dihydrofuran-2(3H)-ones via SmI2-mediated reductive coupling of 2-alkylacrylates of N,N-diisopropyl-2-hydroxybenzamide with aldehydes
  作者：Yecai Lai、Lijie Sun、Man Ki Sit、Yan Wang、Wei-Min Dai

  DOI：10.1016/j.tet.2015.12.009

  日期：2016.2

  acrylates, in both achiral and chiral forms, for accessing substituted dihydrofuran-2(3H)-ones (γ-butyrolactones). Two major issues, concerning with self-dimerization of α-non-branched aliphatic aldehydes and low diastereoselectivity of the products, render limited application of the reductive coupling protocol in total synthesis of natural products. We report here on a novel type of substituted acrylates derived

  io（II）碘化物已被用于介导醛与各种非手性和手性形式的取代丙烯酸酯的还原偶联反应，以获取取代的二氢呋喃2（3 H）-一（γ-丁内酯）。与α-非支链脂族醛的自二聚和产物的低非对映选择性有关的两个主要问题使得还原偶联方案在天然产物的全合成中的应用受到限制。我们在这里报告了一种新型的衍生自2-氨基芳烃（HO-Ar am）的取代丙烯酸酯，例如N，N-二异丙基-2-羟基苯甲酰胺。HO-Ar am的丙烯酸酯使：（a）丙烯酸酯的优先共轭还原比脂族醛的羰基还原优先，从而导致醛的自二聚化减少；（b）在酰胺羰基氧原子和sa（III）之间形成八元环以形成7 / 8-双环过渡态，从而导致the（III）烯醇化物中间体的高度非对映选择性质子化。提供了由HO-Ar am的2-烷基丙烯酸酯和脂族醛合成反式-3,5-二取代的二氢呋喃-2（3 H）-one的实例。
• BIOFUEL PRODUCTION
  申请人：Yoshikuni Yasuo

  公开号：US20090139134A1

  公开（公告）日：2009-06-04

  Methods, enzymes, recombinant microorganism, and microbial systems are provided for converting polysaccharides, such as those derived from biomass, into suitable monosaccharides or oligosaccharides, as well as for converting suitable monosaccharides or oligosaccharides into commodity chemicals, such as biofuels. Commodity chemicals produced by the methods described herein are also provided. Commodity chemical enriched, refinery-produced petroleum products are also provided, as well as methods for producing the same.

  提供了用于将多糖转化为适当的单糖或寡糖的方法、酶、重组微生物和微生物系统，例如从生物质中提取的多糖。同时提供了将适当的单糖或寡糖转化为商品化学品，如生物燃料的方法。本文描述的方法生产的商品化学品也提供了。此外，还提供了商品化学品富集的、精炼生产的石油产品，以及生产这些产品的方法。
• Novel methods of imaging and treatment with targeted compositions
  申请人：——

  公开号：US20030157025A1

  公开（公告）日：2003-08-21

  Novel ultrasound methods comprising administering to a patient a targeted vesicle composition which comprises vesicles comprising a lipid, protein or polymer, encapsulating a gas, in combination with a targeting ligand, and scanning the patient using ultrasound. The scanning may comprise exposing the patient to a first type of ultrasound energy and then interrogating the patient using a second type of ultrasound energy. The targeting ligand preferably targets tissues, cells or receptors, including myocardial cells, endothelial cells, epithelial cells, tumor cells and the glycoprotein GPIIbIIIa receptor. The methods may be used to detect a thrombus, enhancement of an old or echogenic thrombus, low concentrations of vesicles and vesicles targeted to tissues, cells or receptors.

  新型超声波方法包括向患者施加含有脂质、蛋白质或聚合物的气囊组成的有针对性的气囊组合物，该气囊包含一种气体，并与一个靶向配体结合，然后使用超声波扫描患者。扫描可能包括将患者暴露于第一种超声波能量，然后使用第二种超声波能量对患者进行询问。靶向配体首选靶向组织、细胞或受体，包括心肌细胞、内皮细胞、上皮细胞、肿瘤细胞和糖蛋白GPIIbIIIa受体。该方法可用于检测血栓、旧血栓或回声增强、低浓度气囊和靶向组织、细胞或受体的气囊。