O-[(S)-furan-3-yl-[(1S,4S,7R,8R,9S,13R)-8-methyl-5,14-dioxo-6,15-dioxatetracyclo[7.7.0.01,13.04,8]hexadec-11-en-7-yl]methyl] imidazole-1-carbothioate | 1079220-30-6

• 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: O-[(S)-furan-3-yl-[(1S,4S,7R,8R,9S,13R)-8-methyl-5,14-dioxo-6,15-dioxatetracyclo[7.7.0.01,13.04,8]hexadec-11-en-7-yl]methyl] imidazole-1-carbothioate
• CAS: 1079220-30-6
• 化学式: C₂₄H₂₄N₂O₆S
• 分子量: 468.53
• InChiKey: DVUGPQSYBKMFPW-GFBOEHLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O-[(S)-furan-3-yl-[(1S,4S,7R,8R,9S,13R)-8-methyl-5,14-dioxo-6,15-dioxatetracyclo[7.7.0.01,13.04,8]hexadec-11-en-7-yl]methyl] imidazole-1-carbothioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以45%的产率得到(1S,4S,7S,8R,9S,13R)-7-(furan-3-ylmethyl)-8-methyl-6,15-dioxatetracyclo[7.7.0.01,13.04,8]hexadec-11-ene-5,14-dione
  参考文献：
  名称：

  Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity

  摘要：

  Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific x-opioid agonist. Several structural congeners of 1 isolated from Salvia splendens (2-8) together with a series of semisynthetic derivatives (9-24), some of which possess a pyrazoline structural moiety (9, 19-22), have been tested for affinity at human mu, delta, and kappa opioid receptors. None of these compounds showed high affinity binding to these receptors. However, 10 showed modest affinity for kappa receptors suggesting that other natural neoclerodanes from different Salvia species may possess opioid affinity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.043
• 作为产物：
  描述：

  (1S,4S,7R,8R,9S,13R)-7-[(S)-furan-3-yl(hydroxy)methyl]-8-methyl-6,15-dioxatetracyclo[7.7.0.01,13.04,8]hexadec-11-ene-5,14-dione 、 N,N'-硫羰基二咪唑 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到O-[(S)-furan-3-yl-[(1S,4S,7R,8R,9S,13R)-8-methyl-5,14-dioxo-6,15-dioxatetracyclo[7.7.0.01,13.04,8]hexadec-11-en-7-yl]methyl] imidazole-1-carbothioate
  参考文献：
  名称：

  Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity

  摘要：

  Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific x-opioid agonist. Several structural congeners of 1 isolated from Salvia splendens (2-8) together with a series of semisynthetic derivatives (9-24), some of which possess a pyrazoline structural moiety (9, 19-22), have been tested for affinity at human mu, delta, and kappa opioid receptors. None of these compounds showed high affinity binding to these receptors. However, 10 showed modest affinity for kappa receptors suggesting that other natural neoclerodanes from different Salvia species may possess opioid affinity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.043