2,6-dimethyl-2,3,8-octanetriol | 31558-25-5

• 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: 2,6-dimethyl-2,3,8-octanetriol
• 英文别名: 3,7-dimethyl-1,6,7-octanetriol；3,7-dimethyl-octane-1,6,7-triol；3,7-Dimethyl-octan-1,6,7-triol；Dioxycitronellol；'Dioxycitronellol'；3,7-dimethyloctane-1,6,7-triol
• CAS: 31558-25-5
• 化学式: C₁₀H₂₂O₃
• 分子量: 190.283
• InChiKey: HASQLKIWXSMUMF-UHFFFAOYSA-N

物化性质

• 沸点：
  145-150 °C(Press: 1 Torr)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  6
• 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：

  2,6-dimethyl-2,3,8-octanetriol 在 chromium(III) oxide 、 硫酸 作用下， 生成 (R)-(+)-3-甲基己二酸
  参考文献：
  名称：

  Koetz; Steche, Journal fur praktische Chemie (Leipzig 1954), 1924, vol. <2>107, p. 207

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(3,3-二甲基环氧乙烷基)-3-甲基-1-戊醇 在 水 作用下， 反应 1.0h， 以97%的产率得到2,6-dimethyl-2,3,8-octanetriol
  参考文献：
  名称：

  Hot Water-Promoted Ring-Opening of Epoxides and Aziridines by Water and Other Nucleopliles

  摘要：

  Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 degrees C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.

  DOI：

  10.1021/jo702401t

文献信息

• An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)₂, NMO, and Catalytic OsO₄
  作者：K. C. Nicolaou、Vikrant A. Adsool、Christopher R. H. Hale

  DOI：10.1021/ol100290a

  日期：2010.4.2

  PhI(OAc)2 in the presence of OsO4 (cat.) and 2,6-lutidine cleaves olefinic bonds to yield the corresponding carbonyl compounds, albeit, in some cases, with α-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO4 (cat.), 2,6-lutidine, and PhI(OAc)2.

  PhI(OAc) 2在OsO 4 (cat.)和2,6-二甲基吡啶的存在下裂解烯键以产生相应的羰基化合物，尽管在某些情况下，副产物为α-羟基酮。影响烯烃键氧化裂解的更实用和更干净的协议涉及 NMO、OsO 4 (cat.)、2,6-二甲基吡啶和 PhI(OAc) 2。
• Regioselective phosphoranylation and cyclodehydration of triols with diethoxytriphenylphosphorane
  作者：Jeffery W. Kelly、Slayton A. Evans

  DOI：10.1021/ja00284a036

  日期：1986.11

  The structures of the 2,2,2-triphenyl-1,3,2-dioxaphospholanes are readily assessed from /sup n/J/sub /sup 31/P-/sup 13/C/ (n = 2,3) coupling constants and /sup 31/P chemical shifts. Alkyl and aryl substituents attached to the dioxaphospholane ring also induce pronounced substituent shielding effects on the /sup 31/P resonance of the phospholanes. These effects are useful in corroborating the structural

  二乙氧基三苯基膦 (DTPP) 选择性地二膦酰化 1,2,4-三醇中的邻二醇官能团，提供热力学稳定的 2,2,2-三苯基-1,3,2-二氧杂膦。当经受热解条件时，这些二氧杂磷杂环戊烷分解形成瞬态甜菜碱，随后通过三苯基氧化膦的 3-exo-tet 挤出而坍塌成环氧化物。2,2,2-triphenyl-1,3,2-dioxaphospholanes 的结构很容易从 /sup n/J/sub /sup 31/P-/sup 13/C/ (n = 2,3) 耦合评估常数和 /sup 31/P 化学位移。连接到二氧杂磷杂环戊烷环上的烷基和芳基取代基也会对磷杂环戊烷的 /sup 31/P 共振产生显着的取代基屏蔽效应。这些效应有助于证实二氧正膦的结构归属。
• Acidic Three-Liquid-Phase Microemulsion Systems Based on Balanced Catalytic Surfactant for Epoxidation and Sulfide Oxidation under Mild Conditions
  作者：Marion Fressancourt-Collinet、Bing Hong、Loïc Leclercq、Paul. L. Alsters、Jean-Marie Aubry、Véronique Nardello-Rataj

  DOI：10.1002/adsc.201200514

  日期：2013.1.11

  tungstate has been designed as a balanced catalytic surfactant to form acidic three-liquid-phase microemulsion systems at room temperature in the presence of water, a non-chlorinated solvent and dimethyldioctylammonium salts (hydrogen sulfate and dihydrogen phosphate). The triphasic system is efficient for the oxidation of olefins, sulfides and thiophenes under mild conditions. Moreover, the recovery and

  十二烷基二甲基钨酸铵已被设计为一种平衡的催化表面活性剂，可在室温下在水，非氯化溶剂和二甲基二辛基铵盐（硫酸氢盐和磷酸二氢盐）存在下形成酸性三相液相微乳液体系。三相系统在温和条件下对于烯烃，硫化物和噻吩的氧化非常有效。此外，催化剂的回收和可再利用性，产物和催化剂在两个不同相中的直接分离以及可能使用的环境友好溶剂（例如乙酸叔丁酯）使该系统对于涉及过氧化氢的催化氧化反应特别有吸引力。在酸性或中性条件下作为主要氧化剂。
• Mild, effective and selective method for the silylation of alcohols using silazanes promoted by catalytic tetrabutylammonium fluoride
  作者：Yoo Tanabe、Masanari Murakami、Kazuto Kitaichi、Yoshihiro Yoshida

  DOI：10.1016/s0040-4039(00)74419-4

  日期：1994.11

  The presence of catalytic amounts (∼0.02 equiv.) of tetrabutylammonium fluoride (TBAF) significantly promoted the silylation of alcohols using a variety of available silazanes under mild conditions with high chemoselectivity, wherein the choice of silazanes allowed an alternative method for the powerful silylation of various kinds of alcohols or the highly regioselective silylation of primary alcohols

  催化量（〜0.02当量）的四丁基氟化铵（TBAF）在温和的条件下以高化学选择性显着促进了使用各种可用的硅氮烷的醇甲硅烷基化，其中选择硅氮烷可以实现强力甲硅烷基化的另一种方法各种醇或伯醇的高度区域选择性甲硅烷基化。
• Osmium tetraoxide catalyzed vicinal hydroxylation of higher olefins by using hexacyanoferrate(III) ion as a cooxidant
  作者：Makoto Minato、Keiji Yamamoto、Jiro Tsuji

  DOI：10.1021/jo00289a066

  日期：1990.1