3-cyclopropylmethoxy-5-methyl-2,5-cyclohexadiene-1,1-dimethanol | 1194258-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cyclopropylmethoxy-5-methyl-2,5-cyclohexadiene-1,1-dimethanol
• 英文别名: MGD-5-48；[3-(Cyclopropylmethoxy)-1-(hydroxymethyl)-5-methylcyclohexa-2,5-dien-1-yl]methanol
• CAS: 1194258-05-3
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: LQJMIFIFZSUORT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯基氯化硒 、 3-cyclopropylmethoxy-5-methyl-2,5-cyclohexadiene-1,1-dimethanol 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 rac-(1R*,5S*,8S*)-5-cyclopropylmethoxy-3-methyl-8-phenylselenenyl-6-oxabicyclo-[3.2.1]oct-2-ene-1-methanol
  参考文献：
  名称：

  Two Approaches to Diverting the Course of a Free-Radical Cyclization: Application of Cyclopropylcarbinyl Radical Fragmentations and Allenes as Radical Acceptors

  摘要：

  Free radical cyclization of 4 and 7 gave the expected cyclization-reduction products (5 and 8) along with considerable amounts of products derived from a cyclization-atom transfer-secondary cyclization process (6 and 9). Two approaches to avoiding these unexpected products were explored. Use of a cyclopropylcarbinyl fragmentation avoided the secondary cyclization reaction (25 or 43 -> 26 or 44), whereas use of an allene as a radical acceptor avoided the atom-transfer reaction altogether (49 -> 52).

  DOI：

  10.1021/jo901834q
• 作为产物：
  描述：

  3-cyclopropylmethoxy-5-methyl-1-(pivaloyloxymethyl)cyclohexa-2,5-diene-1-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 17.0h， 以69%的产率得到3-cyclopropylmethoxy-5-methyl-2,5-cyclohexadiene-1,1-dimethanol
  参考文献：
  名称：

  Two Approaches to Diverting the Course of a Free-Radical Cyclization: Application of Cyclopropylcarbinyl Radical Fragmentations and Allenes as Radical Acceptors

  摘要：

  Free radical cyclization of 4 and 7 gave the expected cyclization-reduction products (5 and 8) along with considerable amounts of products derived from a cyclization-atom transfer-secondary cyclization process (6 and 9). Two approaches to avoiding these unexpected products were explored. Use of a cyclopropylcarbinyl fragmentation avoided the secondary cyclization reaction (25 or 43 -> 26 or 44), whereas use of an allene as a radical acceptor avoided the atom-transfer reaction altogether (49 -> 52).

  DOI：

  10.1021/jo901834q