(E,5S)-5-hydroxy-3-methyl-5-[(1S,2R)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pent-2-enoic acid | 1416254-88-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (E,5S)-5-hydroxy-3-methyl-5-[(1S,2R)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pent-2-enoic acid
• CAS: 1416254-88-0
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: HVRTYKKUHDCNGO-XXKCFXCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,5S)-5-hydroxy-3-methyl-5-[(1S,2R)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pent-2-enoic acid 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以75%的产率得到(E)-3-methyl-4-[(7R)-1,1,6,7-tetramethyl-2,3,4,7,8,9-hexahydrobenzo[7]annulen-5-yl]but-2-enoic acid
  参考文献：
  名称：

  Scopariusins, A New Class of ent-Halimane Diterpenoids Isolated from Isodon scoparius, and Biomimetic Synthesis of Scopariusin A and Isoscoparin N

  摘要：

  Scopariusins A-C (1-3), three novel rearranged ent-halimanoids with a bicycle[5.4.0]undecane ring system, two new normal ent-halimanoids (4 and 5), and a new ent-clerodanoid (6) were isolated from Isodon scoparius. Moreover, a biomimetic transformation from the ent-clerodanoid to the normal and the rearranged ent-halimane diterpenoids was successfully accomplished, which not only validated the biogenetic hypothesis in this plant but also confirmed the absolute configurations of 1 and 5.

  DOI：

  10.1021/ol303226c
• 作为产物：
  描述：

  (E,5S)-5-acetyloxy-3-methyl-5-[(1S,2R)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pent-2-enoic acid 在 甲醇 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 以95%的产率得到(E,5S)-5-hydroxy-3-methyl-5-[(1S,2R)-1,2,5,5-tetramethyl-2,3,4,6,7,8-hexahydronaphthalen-1-yl]pent-2-enoic acid
  参考文献：
  名称：

  Scopariusins, A New Class of ent-Halimane Diterpenoids Isolated from Isodon scoparius, and Biomimetic Synthesis of Scopariusin A and Isoscoparin N

  摘要：

  Scopariusins A-C (1-3), three novel rearranged ent-halimanoids with a bicycle[5.4.0]undecane ring system, two new normal ent-halimanoids (4 and 5), and a new ent-clerodanoid (6) were isolated from Isodon scoparius. Moreover, a biomimetic transformation from the ent-clerodanoid to the normal and the rearranged ent-halimane diterpenoids was successfully accomplished, which not only validated the biogenetic hypothesis in this plant but also confirmed the absolute configurations of 1 and 5.

  DOI：

  10.1021/ol303226c