2-Bromo-4-(methoxymethoxy)oct-1-ene | 165268-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Bromo-4-(methoxymethoxy)oct-1-ene
• CAS: 165268-65-5
• 化学式: C₁₀H₁₉BrO₂
• 分子量: 251.164
• InChiKey: LDKJKSYJUPRZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-Bromo-4-(methoxymethoxy)oct-1-ene 、 烯丙基溴化镁 在 重水 、 叔丁基锂 、 zinc dibromide 作用下， 生成 5,5-d2-7-(Methoxymethoxy)undec-1-ene
  参考文献：
  名称：

  Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics

  摘要：

  1,1- or n,n-Bismetallic reagents bearing a methoxymethyl ether in the gamma position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes, The nature of the substituents is crucial for this diastereoselection, a pi-chelation between one metal and a properly located unsaturation, as well as 1,2-strain, are proposed to explain the steric outcome of these reactions.

  DOI：

  10.1021/jo00113a032
• 作为产物：
  描述：

  二甲醇缩甲醛 、 2-Bromooct-1-en-4-ol 在 对甲苯磺酸 、 lithium bromide 作用下， 反应 12.0h， 以92%的产率得到2-Bromo-4-(methoxymethoxy)oct-1-ene
  参考文献：
  名称：

  Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics

  摘要：

  1,1- or n,n-Bismetallic reagents bearing a methoxymethyl ether in the gamma position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes, The nature of the substituents is crucial for this diastereoselection, a pi-chelation between one metal and a properly located unsaturation, as well as 1,2-strain, are proposed to explain the steric outcome of these reactions.

  DOI：

  10.1021/jo00113a032

文献信息

• Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics
  作者：Dov Beruben、Ilane Marek、Jean F. Normant、Nicole Platzer

  DOI：10.1021/jo00113a032

  日期：1995.4

  1,1- or n,n-Bismetallic reagents bearing a methoxymethyl ether in the gamma position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes, The nature of the substituents is crucial for this diastereoselection, a pi-chelation between one metal and a properly located unsaturation, as well as 1,2-strain, are proposed to explain the steric outcome of these reactions.