methyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.0^1,10.0^4,9]heptadecane-5-carboxylate | 30217-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: methyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.0^1,10.0^4,9]heptadecane-5-carboxylate
• 英文别名: (3S,6aR,8aS,9R,12aS,12bR)-methyl 3,9,12a-trimethyl-5-oxotetradecahydro-3,6a-methanonaphtho[2,1-d]oxocine-9-carboxylate；ent-8α-Carboxymethyl-13α-hydroxy-13β-methylpodocarpan-19-saeuremethylesterlacton；methyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylate
• CAS: 30217-48-2
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: PQJXALXGEQRZHX-XNRDYXSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.0^1,10.0^4,9]heptadecane-5-carboxylate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 61.0h， 以72%的产率得到methyl (5β,8α,9β,10α,13α)-13-hydroxy-8-(2-hydroxyethyl)-13-methylpodocarpan-15-oate
  参考文献：
  名称：

  Synthesis and pharmacological profile of serofendic acids A and B

  摘要：

  We present efficient syntheses of serofendic acids A and B (SA-A and SA-B), novel neuroprotective substances isolated from fetal calf serum. Biological and pharmacological evaluation showed that SA-A and SA-B have potent protective action aaainst glutarnate-induced neurotoxicity, but do not interact directly with glutamate receptors. A pharmacokinetic study showed that they have good oral bioavailability in rats. The results indicate that SA-A and SA-B are potential lead compounds for candidate drugs to treat various neuroloaical disorders. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.037
• 作为产物：
  描述：

  异甜菊醇 在 氯化亚砜 、 lithium hydroxide monohydrate 、 盐酸羟胺 、 potassium acetate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 54.0h， 生成 methyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.0^1,10.0^4,9]heptadecane-5-carboxylate 、 (3S,4aS,4bS,8R,8aS,10aS)-methyl 2,4b,8-trimethyl-12-oxo-4,4a,4b,5,6,7,8,8a,9,10-decahydro-3H-3,10a-ethanophenanthrene-8-carboxylate
  参考文献：
  名称：

  从异甜菊醇和甜菊醇衍生的骨架多样化和立体化学复杂的文库模板的合成

  摘要：

  我们应用了一种面向多样性的方法，通过对甜菊醇和异甜菊醇的双环 [3.2.1] 辛烷环进行贝克曼重排和贝克曼断裂反应，合成了用于小分子文库生产的骨架多样化和立体化学复杂的模板，糖苷配基来源于二萜天然产物甜菊糖苷。随着光-贝克曼重排的成功应用，介绍了这两种反应途径的优化。这项工作还导致发现了氰基-普林斯型和索普-齐格勒型环化反应。

  DOI：

  10.1021/ol400385w

文献信息

• Synthesis and pharmacological profile of serofendic acids A and B
  作者：Taro Terauchi、Naoki Asai、Takashi Doko、Ryota Taguchi、Osamu Takenaka、Hideki Sakurai、Masahiro Yonaga、Teiji Kimura、Akiharu Kajiwara、Tetsuhiro Niidome、Toshiaki Kume、Akinori Akaike、Hachiro Sugimoto

  DOI：10.1016/j.bmc.2007.07.037

  日期：2007.11

  We present efficient syntheses of serofendic acids A and B (SA-A and SA-B), novel neuroprotective substances isolated from fetal calf serum. Biological and pharmacological evaluation showed that SA-A and SA-B have potent protective action aaainst glutarnate-induced neurotoxicity, but do not interact directly with glutamate receptors. A pharmacokinetic study showed that they have good oral bioavailability in rats. The results indicate that SA-A and SA-B are potential lead compounds for candidate drugs to treat various neuroloaical disorders. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Skeletally Diverse and Stereochemically Complex Library Templates Derived from Isosteviol and Steviol
  作者：Oliver E. Hutt、Trinh L. Doan、Gunda I. Georg

  DOI：10.1021/ol400385w

  日期：2013.4.5

  diverse and stereochemically complex templates for small-molecule library production by performing Beckmann rearrangement and Beckmann fragmentation reactions on the bicyclo[3.2.1]octane rings of steviol and isosteviol, aglycones derived from the diterpene natural product stevioside. The optimization of these two reaction pathways is presented along with the successful application of a photo-Beckmann rearrangement

  我们应用了一种面向多样性的方法，通过对甜菊醇和异甜菊醇的双环 [3.2.1] 辛烷环进行贝克曼重排和贝克曼断裂反应，合成了用于小分子文库生产的骨架多样化和立体化学复杂的模板，糖苷配基来源于二萜天然产物甜菊糖苷。随着光-贝克曼重排的成功应用，介绍了这两种反应途径的优化。这项工作还导致发现了氰基-普林斯型和索普-齐格勒型环化反应。