1-甲氧基-1-己烯-6-醇 | 165064-79-9

• 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: 1-甲氧基-1-己烯-6-醇
• 英文名称: 1-methoxy-1-hexen-6-ol
• 英文别名: 6-methoxy-5-hexen-1-ol；6-methoxyhex-5-en-1-ol；6-Methoxyhex-5-en-1-ol
• CAS: 165064-79-9
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: OJJQEDRXCSRIGK-UHFFFAOYSA-N

物化性质

• 沸点：
  211.7±33.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲氧基-1-己烯-6-醇 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 5A molecular sieve 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 7,7-dimethyl-1-methoxy-(E,Z)-1-octen-6-ol
  参考文献：
  名称：

  基于反转烯醇醚和乙烯酮二硫缩醛极性的氧化环化。四氢呋喃环的构建及其在(+)-Nemorensic酸的合成中的应用

  摘要：

  已经研究了氧化环化反应用于构建四氢呋喃环的效用。在这些实验中，发现醇亲核试剂对于由烯醇醚和烯酮二硫缩醛基团生成的自由基阳离子中间体是有效的陷阱。醇捕获基团的反应性似乎介于烯醇醚和烯丙基硅烷捕获基团的反应性之间。发现源自烯醇醚氧化的环化反应的立体化学结果受立体电子因素控制。这些环化反应的效用通过合成芳樟醇氧化物和轮地辛的关键四氢呋喃结构单元来说明。由乙烯酮二硫缩醛氧化引发的环化反应导致更高水平的立体选择性。这些反应的立体化学结果表明是由涉及较大乙烯酮缩醛基团的空间因素引起的。通过完成 (+)-nemorensic 酸的不对称合成，证明了利用乙烯酮二硫缩醛衍生的自由基阳离子进行环化的合成效用。最后，这些反应被证明与酰胺亲核试剂的使用和内酯产物的直接形成相容。

  DOI：

  10.1021/ja026739l
• 作为产物：
  描述：

  delta-戊内酯 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 生成 1-甲氧基-1-己烯-6-醇
  参考文献：
  名称：

  Preparation of Oxepanes, Oxepenes, and Oxocanes by Iodoetherification using Bis(sym-collidine)iodine(I) Hexafluorophosphate as Electrophile

  摘要：

  Oxepanes have been obtained in good yields (40-95%) by iodoetherification of unsaturated alcohols using bis(sym-collidine)iodine(I) hexafluorophosphate (1) as electrophile, either by 7-exo-mode or 7-endo-mode cyclizations. 4-Oxepenes could also be formed from 4,6-heptadien-1-ols; the presence of a substituent on the carbon 6 appeared necessary, while for steric reasons the presence of a substituent on the carbon 7 was unfavorable. Oxocanes could be obtained in moderate yields (18-27%).

  DOI：

  10.1021/jo960506t

文献信息

• Palladium-Catalyzed Reactions of Enol Ethers: Access to Enals, Furans, and Dihydrofurans
  作者：Matthew G. Lauer、William H. Henderson、Amneh Awad、James P. Stambuli

  DOI：10.1021/ol3028994

  日期：2012.12.7

  The palladium-catalyzed oxidation of alkyl enol ethers to enals, which employs low loadings of a palladium catalyst, is described. The mild oxidation conditions tolerate a diverse array of functional groups, while allowing the formation of di-, tri-, and tetrasubtituted olefins. The application of this methodology to intramolecular reactions of alkyl enol ethers containing pendant alcohols provides

  描述了使用低负载量的钯催化剂的钯催化的烯醇醚氧化为烯醛。温和的氧化条件可耐受各种官能团，同时允许形成二，三和四取代的烯烃。该方法在含有侧链醇的烷基烯醇醚的分子内反应中的应用提供了呋喃和2，5-二氢呋喃产物。
• A new method for the preparation of the 6,6 and 6,7 ring systems of bicyclic ethers
  作者：Fabienne Simart、Yves Brunel、Sylvie Robin、Gérard Rousseau

  DOI：10.1016/s0040-4020(98)00833-3

  日期：1998.10

  Preparation of 2,7-dioxabicyclo[4.4.0]decane and 2,8-dioxabicyclo[5.4.0]undecane derivatives in five steps from dihydropyran are reported. Transformation of 3-bromo-2-allyloxepane into 2,7-dioxabicyclo-[5.4.0]-undecane is also described.

  据报道，由二氢吡喃分五步制备2，7-二氧杂双环[4.4.0]癸烷和2，8-二氧杂双环[5.4.0]十一烷衍生物。还描述了3-溴-2-烯丙基环庚烷向2，7-二氧杂双环-[5.4.0]-十一烷的转化。
• Intramolecular anodic olefin coupling reactions: the use of bis enol ether substrates
  作者：Kevin D. Moeller、Luzviminda V. Tinao

  DOI：10.1021/ja00029a036

  日期：1992.1

  In an effort to develop electrochemical methods for directly initiating oxidative cyclization reactions, the anodic oxidation of bis enol ether substrates has been examined. The reactions were found to lead to the formation of five-, six-, and seven-membered-ring 1,4-dicarbonyl equivalents. The reactions were not found to be useful for generating larger ring sizes. Both alkyl and silyl enol ether substrates were found to be compatible with the conditions required for carbon-carbon bond formation. Cyclic voltammetry studies indicated that the cyclizations were fast and that the reactions happened at or near the electrode surface. Finally, the cyclization reactions were shown to be compatible with the formation of quaternary carbons, even when carbon-carbon bond formation involved the generation of two vicinal quaternary carbons.
• Synthesis of Fluorogenic Polymers for Visualizing Cellular Internalization
  作者：Shane L. Mangold、Rachael T. Carpenter、Laura L. Kiessling

  DOI：10.1021/ol800932w

  日期：2008.7.17

  The binding of a polymeric ligand to a cell surface receptor can promote its internalization. Methods to track and visualize multivalent ligands within a cell can give rise to new therapeutic strategies and illuminate signaling processes. We have used the features of the ring-opening metathesis polymerization (ROMP) to develop a general strategy for synthesizing multivalent ligands equipped with a latent fluorophore. The utility of ligands of this type is highlighted by visualizing multivalent antigen internalization in live B cells.
• Reversing the Polarity of Enol Ethers:  An Anodic Route to Tetrahydrofuran and Tetrahydropyran Rings
  作者：Angela Sutterer、Kevin D. Moeller

  DOI：10.1021/ja001063k

  日期：2000.6.1