ethyl 2-[1-(2,3-dimethoxy-5-methylphenyl)-5,5-dimethylcyclopent-2-enyl]acetate | 882512-65-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl 2-[1-(2,3-dimethoxy-5-methylphenyl)-5,5-dimethylcyclopent-2-enyl]acetate
• 英文别名: Ethyl 2-[1-(2,3-dimethoxy-5-methylphenyl)-5,5-dimethylcyclopent-2-en-1-yl]acetate
• CAS: 882512-65-4
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: ZYQABCYEQAUFGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-[1-(2,3-dimethoxy-5-methylphenyl)-5,5-dimethylcyclopent-2-enyl]acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 3.0h， 以99%的产率得到ethyl 2-[1-(2,3-dimethoxy-5-methylphenyl)-2,2-dimethylcyclopent-1-yl]acetate
  参考文献：
  名称：

  Total synthesis of (±)-herbertenediol

  摘要：

  A formal total synthesis of the sesquiterpene (+/-)-herbertenediol and its dimers mastigophorenes A-D has been accomplished, starting from vanillin via 2,3-dimethoxy-5-methylbenzaldehyde. A combination of Claisen rearrangement and ring-closing metathesis reactions were employed for the generation of the two vicinal quaternary carbons on a cyclopentane ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.021
• 作为产物：
  描述：

  3-溴-4,5-二甲氧基苯甲醛 在 Grubbs catalyst first generation 、 Lindlar's catalyst sodium tetrahydroborate 、 三氟化硼乙醚 、 氢气 、 silica gel 、 lithium 、 sodium cyanoborohydride 、 丙酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 125.5h， 生成 ethyl 2-[1-(2,3-dimethoxy-5-methylphenyl)-5,5-dimethylcyclopent-2-enyl]acetate
  参考文献：
  名称：

  Total synthesis of (±)-herbertenediol

  摘要：

  A formal total synthesis of the sesquiterpene (+/-)-herbertenediol and its dimers mastigophorenes A-D has been accomplished, starting from vanillin via 2,3-dimethoxy-5-methylbenzaldehyde. A combination of Claisen rearrangement and ring-closing metathesis reactions were employed for the generation of the two vicinal quaternary carbons on a cyclopentane ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.021

文献信息

• Total synthesis of (±)-herbertenediol
  作者：A. Srikrishna、G. Satyanarayana

  DOI：10.1016/j.tet.2006.01.021

  日期：2006.3

  A formal total synthesis of the sesquiterpene (+/-)-herbertenediol and its dimers mastigophorenes A-D has been accomplished, starting from vanillin via 2,3-dimethoxy-5-methylbenzaldehyde. A combination of Claisen rearrangement and ring-closing metathesis reactions were employed for the generation of the two vicinal quaternary carbons on a cyclopentane ring. (c) 2006 Elsevier Ltd. All rights reserved.