3-Methoxy-1-hexene | 108811-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methoxy-1-hexene
• 英文别名: 3-methoxyhexene-1；3-methoxyhex-1-ene
• CAS: 108811-41-2
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: SMUGKXLDEHHFJD-UHFFFAOYSA-N

物化性质

• 沸点：
  113.3±9.0 °C(Predicted)
• 密度：
  0.782±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-Methyloxy-5-hexen-1-ol mesylate 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 丙酮 、 苯 为溶剂， 反应 11.75h， 生成 3-Methoxy-1-hexene
  参考文献：
  名称：

  Cyclization of (4-Methoxy-5-hexenyl)lithium

  摘要：

  The cyclization of (4-methoxy-5-hexenyl)lithium (1), which was prepared by lithium-iodine exchange between 3-methoxy-6-iodo-1-hexene (2) and 1.75 molar equiv of t-BuLi in diethyl ether-n-pentane solution at -78 degrees C, has been investigated in a variety of solvent systems. The isomeric composition of the cis- and trans-1-methoxy-2-methylcyclopentane produced upon cyclization of 1 followed by quench with MeOH has been found to be dramatically dependent on the solvent system in which the isomerization is conducted.

  DOI：

  10.1021/jo00101a010

文献信息

• Stereochemistry of the cyclization of alkoxy-substituted 5-hexenyllithiums: effect of solvent and lithium iodide on diastereoselectivity
  作者：William F. Bailey、Xinglong Jiang

  DOI：10.1016/j.tet.2005.01.042

  日期：2005.3

  The stereochemistry of the cyclization of 4-methoxy-5-hexenyllithium, 4-(methoxymethoxy)-5-hexenyllithium, 4-tert-butoxy-5-hexenyllithium, and 3-methoxy-5-hexenyllithium, each of which was generated from the corresponding iodide by low-temperature lithium–iodine exchange, has been studied in a variety of solvent systems. The results of these studies demonstrate that the stereochemical outcome of the

  4-甲氧基-5-己烯基锂，4-（甲氧基甲氧基）-5-己烯基锂，4-叔丁氧基-5-己烯基锂和3-甲氧基-5-己烯基锂环化的立体化学通过低温锂-碘交换得到相应的碘化物，已在多种溶剂系统中进行了研究。这些研究的结果表明，烷氧基取代的5-己烯基锂环化的立体化学结果可能会受到进行闭环的介质的深刻影响。这些通常具有显着溶剂作用的病因归因于某些亲硫性配体竞争性络合碘化锂盐的能力，碘化锂盐是作为用于制备有机锂的交换反应的副产物而存在的。
• [DE] VERFAHREN ZUR KATALYTISCHEN ADDITION VON NUCLEOPHILEN AN ALKINE ODER ALLENE<br/>[EN] PROCESS FOR CATALYTIC ADDITION OF NUCLEOPHILES TO ALKINES OR ALLENES<br/>[FR] PROCEDE D'ADDITION CATALYTIQUE DE NUCLEOPHILES ET D'ALCYNES OU D'ALLENES
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：WO1997021648A1

  公开（公告）日：1997-06-19

  (DE) Verfahren zur katalytischen Addition von nucleophilen Agentien an Alkine oder Allene unter Bildung von durch das Nucleophil substituierten Alkenen, die gegebenenfalls mit dem Nucleophil weiterreagieren und/oder isomerisieren, wobei man als Katalysator zumindest teilweise in ionisierter Form vorliegende Komplexe des einwertigen Golds verwendet.(EN) A process is disclosed for the catalytic addition of nucleophilic agents to alkines or allenes to form alkenes that are substituted by the nucleophile and where required undergo further reaction and/or isomerisation with the nucleophile. The catalyst used is a monovalent gold complex which is present at least in part in ionised form.(FR) L'invention concerne un procédé d'addition catalytique d'agents nucléophiles et d'alcynes ou d'allènes avec formation d'alcènes substitués par le nucléophile. Les alcènes ainsi obtenus continuent éventuellement à réagir et à s'isomérer avec le nucléophile. On utilise comme catalyseur les complexes de l'or monovalent présents au moins en partie sous forme ionisée.

  一种催化的核ophilic加成到烯烃或 diyne，并形成带有核ophil取代的烯烃，随后可能与核ophil继续反应或进行异构化。所使用的催化物是单价金复合物，这些催化物至少以离解形式存在。
• Anion Structure Determination in the Gas Phase:  Chemical Reactivity as a Probe
  作者：Jeehiun K. Lee、Joseph J. Grabowski

  DOI：10.1021/jo961463j

  日期：1996.1.1

  In the gas phase, the discrimination between two isomeric anion structures is a challenge that requires different solutions for different applications. The anionic oxy-Cope rearrangement involves the rearrangement of an alkoxide to an isomeric enolate; the mechanistic study of such a process in the gas phase requires a simple and selective probe process. Using a flowing afterglow mass spectrometer, we have examined the utility and limitations of using chemical reactivity to discriminate between alkoxides and enolates in the gas phase. A series of alkoxides and enolates were allowed to react with three chemical probe reagents: methanol-O-d, methyl nitrite, and dimethyl disulfide. Quantitative and qualitative characterization of each probe reagent reveals the especially broad and flexible utility of dimethyl disulfide as a chemical probe. Dimethyl disulfide is a selective reagent with ambident behavior that reacts efficiently with all anions studied and fully capitalizes on the structure/reactivity differences between alkoxides and enolates. Alkoxides behave as classical ''hard bases'' when allowed to react with dimethyl disulfide, effecting elimination across the C-S bond, whereas enolates, ''soft bases'', attack at sulfur. Methyl nitrite is also a selective ambident probe reagent but, due to its particularly slow reaction with enolates, is useful only in conjunction with a more reliable probe such as dimethyl disulfide. Methanol-O-d, for a variety of reasons detailed in the paper, is unsuitable as a chemical probe reagent for the unequivocal discernment between alkoxides and enolates.
• Bailey William F., Jiang Xing-Long, J. Org. Chem, 59 (1994) N 22, S 6528-6533
  作者：Bailey William F., Jiang Xing-Long

  DOI：——

  日期：——
• VERFAHREN ZUR KATALYTISCHEN ADDITION VON NUCLEOPHILEN AN ALKINE ODER ALLENE
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0873289B1

  公开（公告）日：2000-05-03