2-Methoxy-4-(2-methoxypropan-2-yloxy)hexa-1,5-diene | 201019-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methoxy-4-(2-methoxypropan-2-yloxy)hexa-1,5-diene
• CAS: 201019-78-5
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: FDKFWAXYSHBUDD-UHFFFAOYSA-N

物化性质

• 沸点：
  216.9±40.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methoxy-4-(2-methoxypropan-2-yloxy)hexa-1,5-diene 在 四丙基高钌酸铵 N-溴代丁二酰亚胺(NBS) 、 N-甲基吲哚酮 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 potassium carbonate 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (1,2-dihydroxy-4,4-dimethoxy-cyclopentyl)-acetic acid tert-butyl ester
  参考文献：
  名称：

  A remarkable ene-like reaction: Development and synthetic applications

  摘要：

  A catalytic ene-like reaction of aldehydes with those vinyl ethers that display the oxygen functionality at the central carbon of an allylic system, e.g., 2-methoxypropene, is discussed in detail. The reaction is promoted by 0.05 eguiv. of the 1:1 complex of Yb(fod)(3) and acetic acid, and it is forms the centerpiece of our synthesis of chlorovulone II, mitomycinoids and phyllanthocin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01016-8
• 作为产物：
  描述：

  2-甲氧基丙烯 、 丙烯醛 在 tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium silica gel 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到2-Methoxy-4-(2-methoxypropan-2-yloxy)hexa-1,5-diene
  参考文献：
  名称：

  A remarkable ene-like reaction: Development and synthetic applications

  摘要：

  A catalytic ene-like reaction of aldehydes with those vinyl ethers that display the oxygen functionality at the central carbon of an allylic system, e.g., 2-methoxypropene, is discussed in detail. The reaction is promoted by 0.05 eguiv. of the 1:1 complex of Yb(fod)(3) and acetic acid, and it is forms the centerpiece of our synthesis of chlorovulone II, mitomycinoids and phyllanthocin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01016-8

文献信息

• Practical Synthesis of (±)-Chlorovulone II
  作者：Marco A. Ciufolini、Shuren Zhu

  DOI：10.1021/jo972073f

  日期：1998.3.1

  We describe a total synthesis of (+/-)-chlorovulone II that is 10 steps shorter than the best alternative currently available (nine vs 19 steps). The key event of the synthesis is an aldol addition of the enolate of ethyl acetate into 4-cyclopentene-1,3-dione, a substance that has received little attention as an educt for prostanoid synthesis and for which little is known about carbonyl 1,2-addition with enolates. In addition, we provide chemical and stereochemical details of a route to a key intermediate toward the title compound that involves a carbonyl-ene reaction and a radical addition to an aldehyde carbonyl.