methyl-(3-methyl-1-propyl-but-3-enyl)-ether | 68105-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-(3-methyl-1-propyl-but-3-enyl)-ether
• 英文别名: Methyl-(3-methyl-1-propyl-but-3-enyl)-aether；4-Methoxy-2-methyl-hept-1-en；4-methoxy-2-methylhept-1-ene
• CAS: 68105-13-5
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: HOUOEFUTWJDFRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  10.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  methyl-(3-methyl-1-propyl-but-3-enyl)-ether 、 乙腈 以31%的产率得到
  参考文献：
  名称：

  GEVORKYAN A. A.; TOKMADZHYAN G. G., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1978, 31, HO 7, 536-538

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Methoxy-6-phenylsulfanylmethyl-hept-6-en-2-ol 在 吡啶 、 偶氮二异丁腈 、 三苯基氢化锡 、 lithium bromide 作用下， 以 四氢呋喃 、 氘代苯 为溶剂， 反应 4.0h， 生成 methyl-(3-methyl-1-propyl-but-3-enyl)-ether
  参考文献：
  名称：

  [3 + 3] Annulation Based on 6-Endo-Trig Radical Cyclization: Regioselectivity and Diastereoselectivity

  摘要：

  The development of a [3 + 3] annulation strategy based on sequential ''two-electron'' and ''one-electron'' allylation of beta-substituted aldehydes and derivatives with the bifunctional isobutene conjunctive reagent 1 is described. The key step involves an unusual 6-endo-trig radical cyclization. Yields of 6-endo products are improved if the PhS group is oxidized to a PhSO(2) group prior to cyclization. The structural factors affecting the regioselectivity and stereoselectivity of the cyclization are examined. In general, the stereoselectivity of 6-endo-trig cyclization of 5-hexenyl radicals can be rationalized by conformational analysis of chairlike transition states and can be calculated effectively with an MM2 force field model, High 6-endo regioselectivity requires a strong driving force. Fragmentable allylic groups (R(3)Sn, PhSO(2), and to a lesser extent PhS) are shown to be sufficiently activating to achieve 6-endo regioselectivity.

  DOI：

  10.1021/jo00129a024

文献信息

• Paul; Tchelitcheff, Bulletin de la Societe Chimique de France, 1951, p. 125,127
  作者：Paul、Tchelitcheff

  DOI：——

  日期：——