7-methoxy-hept-6-en-1-ol | 287171-71-5

• 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: 7-methoxy-hept-6-en-1-ol
• 英文别名: 7-methoxy-6-hepten-1-ol；7-Methoxyhept-6-en-1-ol；7-methoxyhept-6-en-1-ol
• CAS: 287171-71-5
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: FKMZWHALUTZBAD-UHFFFAOYSA-N

物化性质

• 沸点：
  221.2±23.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  7-methoxy-hept-6-en-1-ol 在 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 Angstroem MS 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 1-(trimethylsilyl)-1,8-dimethoxyocta-1,7-diene
  参考文献：
  名称：

  富电子烯烃的阳极氧化：基于自由基阳离子的桥联双环骨架合成方法

  摘要：

  已经研究了分子内阳极烯烃偶联反应在构建双环[3.2.1]辛烷环骨架中的应用。尽管使用双烯醇醚底物的简单模型系统容易导致双环产物的形成，但是由于在环化反应的末端和起始端均形成二甲氧基缩醛基团的反应阻碍了该反应在全合成工作中的应用。为了解决该问题，已经研究了基于乙烯酮缩醛的引发基团。烯酮二硫缩醛基的使用被证明对于该目的特别有用。

  DOI：

  10.1016/s0040-4020(01)00358-1
• 作为产物：
  描述：

  1-己醇,6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]- 在 四丁基氟化铵 、 苯基锂 作用下， 生成 7-methoxy-hept-6-en-1-ol
  参考文献：
  名称：

  Nagano; Tada; Isobe, Synlett, 2000, # 8, p. 1193 - 1195

  摘要：

  DOI：

文献信息

• Anodic cyclization reactions: probing the chemistry of N,O-ketene acetal derived radical cations
  作者：Yung-tzung Huang、Kevin D. Moeller

  DOI：10.1016/j.tet.2006.04.009

  日期：2006.7

  The chemical reactivity of radical cations derived from N,O-ketene acetals has been examined and compared with the reactivity of radical cations derived from both ketene dithioacetals and enol ethers. Synthetically, the N,O-ketene acetal radical cations lead to more efficient cyclization reactions than either the ketene dithioacetal or enol ether derived radical cations. Cyclic voltammetry experiments

  已经检查了衍生自N，O-酮烯缩醛的自由基阳离子的化学反应性，并将其与衍生自烯酮二硫缩醛和烯醇醚的自由基阳离子的反应性进行了比较。合成地，N，O-烯酮缩醛自由基阳离子比烯酮二硫缩醛或烯醇醚衍生的自由基阳离子导致更有效的环化反应。使用烯丙基硅烷捕获基团的循环伏安法实验表明，这些环化的效率并非归因于N，O-烯酮缩醛自由基阳离子更具反应性，但对分解更稳定。最后，研究了使用手性氧唑烷酮的环化反应。
• Preparation of Oxepanes, Oxepenes, and Oxocanes by Iodoetherification using Bis(<i>sym</i>-collidine)iodine(I) Hexafluorophosphate as Electrophile
  作者：Yves Brunel、Gérard Rousseau

  DOI：10.1021/jo960506t

  日期：1996.1.1

  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%).
• One-flask, regiospecific conversions of allylic alcohols into 2-carbon-extended, conjugated dienoate esters. Use of a new sulfinyl orthoester
  作者：Gary H. Posner、R. David Crouch、Chris M. Kinter、Jean Christophe Carry

  DOI：10.1021/jo00025a008

  日期：1991.12

  Sixteen differently substituted primary and secondary allylic alcohols are shown to react with sulfinyl orthoacetate 1 at 100-degrees-C sequentially via a [3,3] sigmatropic rearrangement and then a beta-elimination of benzenesulfenic acid to form conjugated dienoate esters 5-13 in 45-95% yields. This one-flask, intramolecular carbon-carbon bond-forming process represents a simple and convenient method for regiospecific gamma-attachment of a two-carbon (ethoxycarbonyl)methylene unit via the synthetic equivalent of an S(N)2' process. Two examples are given in which rationally designed dienoates 20 and 24, prepared via this one-flask process and carrying a pendant alkene unit, undergo intramolecular 2 + 4 cycloaddition producing bicyclic cyclohexenes 21 and 25.
• Construction of dihydropyran-bridged macrocycles by inverse-electron-demand Diels–Alder reaction
  作者：Xiaomei Dong、Qingxia Wang、Qian Zhang、Shuai Xu、Zhihong Wang

  DOI：10.1016/j.tet.2013.10.101

  日期：2013.12

  A variety of dihydropyran-bridged macrocyclic structures were constructed by the inverse-electron-demand Diels Alder reaction of 2-oxo-4-aryl-but-3-enoates. Controlling of the tether length and the position of the activating substituent in the substrates would guide the reaction to the formation of four different types of polycyclic frames, namely bicyclic [n.3.1], bicyclic [n.2.2], tricyclic [n.3.1.1], and tricyclic [n.2.2.2] macrocycles. The intermolecular/intramolecular selectivity of the Diels Alder reaction was virtually governed by the tether length. The reactions were carried out rapidly under mild conditions, and offered a practical method for creating bridged polycyclic structures with large rings from acyclic precursors. (C) 2013 Elsevier Ltd. All rights reserved.
• Intramolecular Anodic Olefin Coupling Reactions: A New Approach to the Synthesis of Angularly Fused, Tricyclic Enones
  作者：Luzviminda V. Tinao-Wooldridge、Kevin D. Moeller、Christine M. Hudson

  DOI：10.1021/jo00088a019

  日期：1994.5

  A number of intramolecular anodic olefin coupling reactions have been examined in order to determine the feasibility of using a sequential electrochemical oxidation-aldol condensation approach for constructing polycyclic enones. Initially, substrates comprised of an aldehyde enol ether tethered to a ketone enol ether were examined. In a model study, it was shown that such a substrate could lead to a successful electrochemical oxidation-aldol condensation sequence. However, the difficulties associated with both the synthesis and the poor stability of the ketone enol ethers greatly reduced the potential utility of this approach. This problem was circumvented by taking advantage of the compatibility of allylsilane groups with the electrolysis reaction. In these examples, ozonolysis of the electrochemical cyclization product afforded the 1,4-dicarbonyl substrate needed for the aldol condensation. The use of the less reactive allylsilane group in the electrochemical reaction still allowed for the construction of quaternary carbons. Finally a pair of angularly fused, tricyclic enones were synthesized. The regiochemistry of the enone in the product could be controlled by the proper choice of the substrate for the electrolysis and manipulation of the resulting cyclized product.