3,7-Dimethyl-4-oxa-1,6-octadiene | 79705-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-Dimethyl-4-oxa-1,6-octadiene
• 英文别名: 3-[(3-Methylbut-2-en-1-yl)oxy]but-1-ene；1-but-3-en-2-yloxy-3-methylbut-2-ene
• CAS: 79705-00-3
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: YYOIINOBDYCMCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,7-Dimethyl-4-oxa-1,6-octadiene 在 calcium hypochlorite 作用下， 以 二氯甲烷 、 水 为溶剂， 以74%的产率得到3-Chloro-2-methyl-4-(1-methyl-allyloxy)-but-1-ene
  参考文献：
  名称：

  New diene formation by ene-type chlorination and palladium catalyzed dehydrochlorination: Synthesis of citral from diprenyl ether

  摘要：

  DOI：

  10.1016/s0040-4039(00)94188-1
• 作为产物：
  描述：

  3-丁烯-2-醇 、 1-溴-3-甲基-2-丁烯 在 sodium hydroxide 、 四丁基溴化铵 作用下， 反应 15.0h， 以73%的产率得到3,7-Dimethyl-4-oxa-1,6-octadiene
  参考文献：
  名称：

  1,2- and 1,5-stereocontrols in 5-hexenyl radical intramol cyclocondensations: cooperative or antagonist effect. Confrontation of experimental results with MM2 calculations of transition states

  摘要：

  The cyclofunctionalization of 1,6-dienes 1 and 2 via the addition of tosyl radical allows the analysis of the combined effects of 1,2- and 1,5-stereocontrols on the outcome of 5-hexenyl radical cyclizations. MM2 calculations of transition states agree quite well with the experimental selectivity, i.e., exclusive 1,2-trans control, and predominance of 1,5-cis over 1,5-trans relationship. The addition of TsBr to carbohydrate-derived epimeric dienes 3a and 3b shows that the stereochemistry of the newly formed C-C bond is controlled by the configuration of the C2 center of the radical. 1,5-trans or 1,5-cis selectivity can be achieved depending on the configuration of C2.

  DOI：

  10.1021/jo00124a012

文献信息

• [2,3]-Wittig rearrangement of unsymmetrical bis-allylic ethers. Facile method for regio- and stereoselective synthesis of 1,5-dien-3-ols
  作者：T. Nakai、K. Mikami、S. Taya、Y. Fujita

  DOI：10.1021/ja00411a038

  日期：1981.10
• NAKAI, T.;MIKAMI, K.;TAYA, S.;FUJITA, Y., J. AMER. CHEM. SOC., 1981, 103, N 21, 6492-6494
  作者：NAKAI, T.、MIKAMI, K.、TAYA, S.、FUJITA, Y.

  DOI：——

  日期：——
• SUZUKI, SHIGEAKI;KANEHIRA, KOICHI;FUJITA, YOSHIJI;OTERA, JUNZO, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM., 1985, N 3, 552-557
  作者：SUZUKI, SHIGEAKI、KANEHIRA, KOICHI、FUJITA, YOSHIJI、OTERA, JUNZO

  DOI：——

  日期：——
• New diene formation by ene-type chlorination and palladium catalyzed dehydrochlorination: Synthesis of citral from diprenyl ether
  作者：Shigeaki Suzuki、Yoshiji Fujita、Takashi Nishida

  DOI：10.1016/s0040-4039(00)94188-1

  日期：1983.1
• 1,2- and 1,5-stereocontrols in 5-hexenyl radical intramol cyclocondensations: cooperative or antagonist effect. Confrontation of experimental results with MM2 calculations of transition states
  作者：M. P. Bertrand、I. De Riggi、C. Lesueur、S. Gastaldi、R. Nouguier、C. Jaime、A. Virgili

  DOI：10.1021/jo00124a012

  日期：1995.9

  The cyclofunctionalization of 1,6-dienes 1 and 2 via the addition of tosyl radical allows the analysis of the combined effects of 1,2- and 1,5-stereocontrols on the outcome of 5-hexenyl radical cyclizations. MM2 calculations of transition states agree quite well with the experimental selectivity, i.e., exclusive 1,2-trans control, and predominance of 1,5-cis over 1,5-trans relationship. The addition of TsBr to carbohydrate-derived epimeric dienes 3a and 3b shows that the stereochemistry of the newly formed C-C bond is controlled by the configuration of the C2 center of the radical. 1,5-trans or 1,5-cis selectivity can be achieved depending on the configuration of C2.