3-(甲氧基甲氧基)己-1-烯 | 104620-58-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(甲氧基甲氧基)己-1-烯
• 英文名称: 3-(methoxymethoxy)-1-hexene
• 英文别名: 3-(Methoxymethoxy)hex-1-ene
• CAS: 104620-58-8
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: IQXDWNLDENVLFP-UHFFFAOYSA-N

物化性质

• 沸点：
  68-70 °C(Press: 50 Torr)
• 密度：
  0.854±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(甲氧基甲氧基)己-1-烯 在 三氯化硼 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 1.0h， 生成 1-<(1'-hexen-3'-yloxy)methyl>-2-<(hydroxyimino)methyl>-3-methylimidazolium chloride
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralykyloxy)methyl quaternarized 2-[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication

  摘要：

  A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methyli midazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissociation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.

  DOI：

  10.1021/jm00122a035
• 作为产物：
  描述：

  6-chloro-1-hexen-3-ol 在 叔丁基锂 、 phosphorus pentoxide 、 sodium iodide 作用下， 以 乙醚 、 氯仿 、 丙酮 、 正戊烷 为溶剂， 反应 3.0h， 生成 3-(甲氧基甲氧基)己-1-烯
  参考文献：
  名称：

  烷氧基取代的5-己烯基锂环化的立体化学：溶剂和碘化锂对非对映选择性的影响

  摘要：

  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。

  DOI：

  10.1016/j.tet.2005.01.042

文献信息

• ORGANOCATALYTIC PROCESS FOR ASYMMETRIC SYNTHESIS OF DECANOLIDES
  申请人：Council of Scientific and Industrial Research

  公开号：US20160272608A1

  公开（公告）日：2016-09-22

  The present invention discloses organocatalytic process for asymmetric synthesis of highly enantioselective decanolide compounds in high yield with >99% ee. Further, the present invention disclose cost effective, improved organocatalytic process for asymmetric synthesis of highly enantioselective decanolides compounds from non-chiral, cheap, easily available raw materials.

  本发明揭示了一种有机催化过程，用于高产率合成高对映选择性的十内酯化合物，其对映异构体纯度>99%。此外，本发明揭示了一种成本效益高、改进的有机催化过程，用于从非手性、廉价、易得原料中合成高对映选择性的十内酯化合物。
• Cleavage of methoxymethyl ethers with boron trichloride. A convenient, versatile preparation of chloromethyl ether derivatives
  作者：Dane A. Goff、Ralph N. Harris、Jeffrey C. Bottaro、Clifford D. Bedford

  DOI：10.1021/jo00374a040

  日期：1986.11
• GOFF D. A.; HARRIS R. N., III; BOTTARO J. C.; BEDFORD C. D., J. ORG. CHEM., 51,(1986) N 24, 4711-4714
  作者：GOFF D. A.、 HARRIS R. N., III、 BOTTARO J. C.、 BEDFORD C. D.

  DOI：——

  日期：——
• US9765048B2
  申请人：——

  公开号：US9765048B2

  公开（公告）日：2017-09-19
• Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralykyloxy)methyl quaternarized 2-[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication
  作者：Clifford D. Bedford、Ralph N. Harris、Robert A. Howd、Dane A. Goff、Gary A. Koolpe、M. Petesch、Irwin Koplovitz、Walter E. Sultan、H. A. Musallam

  DOI：10.1021/jm00122a035

  日期：1989.2

  A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methyli midazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissociation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.