methyl (1aS,3aS,7aR,7bR)-octahydro-1a,6,6-trimethyl-7b-(2-oxoethyl)naphtho[1,2-b]oxirene-3a(1aH)-carboxylate | 611234-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: methyl (1aS,3aS,7aR,7bR)-octahydro-1a,6,6-trimethyl-7b-(2-oxoethyl)naphtho[1,2-b]oxirene-3a(1aH)-carboxylate
• 英文别名: methyl (1aS,3aS,7aR,7bR)-1a,6,6-trimethyl-7b-(2-oxoethyl)-2,3,4,5,7,7a-hexahydronaphtho[1,2-b]oxirene-3a-carboxylate
• CAS: 611234-01-6
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: XNHXQXSZFSFHGI-ISWURRPUSA-N

物化性质

• 沸点：
  363.5±17.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1aS,3aS,7aR,7bR)-octahydro-1a,6,6-trimethyl-7b-(2-oxoethyl)naphtho[1,2-b]oxirene-3a(1aH)-carboxylate 反应 168000.0h， 以45%的产率得到(2S,4aS,8aS)-2-Hydroxy-2,7,7-trimethyl-1-[2-oxo-eth-(E)-ylidene]-octahydro-naphthalene-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  Reactivity of Chiral Sesquiterpene Synthons Obtained by the Degradation of Maslinic Acid from Olive‐Pressing Residues

  摘要：

  Maslinic acid, a naturally occurring compound isolated from the solid wastes of olive-oil pressing, was fragmented through the C-ring via oxidative procedures to obtain two structural fragments. The chemical behaviors of cis-decalin, from the D and E rings, and of trans-decalin fragments, from the A and B rings, were investigated in depth using several chemical and enzymatic reactions. These decalin chiral synthons are interesting intermediates to semisynthesize phenanthrene- and drimane-type compounds and natural tricyclic triterpenes.

  DOI：

  10.1080/00397910600773858
• 作为产物：
  描述：

  山楂酸 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 臭氧 、 间氯过氧苯甲酸 作用下， 以 吡啶 、 四氯化碳 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.58h， 生成 methyl (1aS,3aS,7aR,7bR)-octahydro-1a,6,6-trimethyl-7b-(2-oxoethyl)naphtho[1,2-b]oxirene-3a(1aH)-carboxylate
  参考文献：
  名称：

  Degradation of triterpenic compounds from olive-pressing residues. Synthesis of trans-decalin type chiral synthons

  摘要：

  Three seco-Gring triterpenic compounds were obtained from oleanolic or maslinic acids from olive-mill solid wastes by photochemical and chemical reactions. From these oleantriene compounds, different remarkable sesquiterpene and nor-sesquiterpene fragments such as 3beta-hydroxydrimenol (13) and epoxydecalone (16) were achieved through oxidative cleavages of the double bonds in the opened Gring. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01634-4

文献信息

• Bioactive Compounds with Added Value Prepared from Terpenes Contained in Solid Wastes from the Olive Oil Industry
  作者：Andres Parra、Pilar E. Lopez、Andres Garcia-Granados

  DOI：10.1002/cbdv.200900023

  日期：2010.2

  pentacyclic triterpenes oleanolic acid and maslinic acid were isolated. These natural compounds were transformed into methyl olean‐12‐en‐28‐oate (5), which then was transformed into several seco‐C‐ring triterpene compounds by chemical and photolytic modifications. The triene seco‐products were fragmented through several oxidative procedures to produce, simultaneously, cis‐ and trans‐decalin derivatives, both

  从两相橄榄油提取的固体废物中分离出五环三萜齐墩果酸和山楂酸。这些天然化合物被转化为 olean-12-en-28-oate (5)，然后通过化学和光解修饰转化为几种 seco-C 环三萜化合物。三烯 seco 产物通过几种氧化程序被裂解，同时产生顺式和反式十氢化萘衍生物，这两种都是生物活性化合物的潜在合成子。研究了分离片段的化学行为，并对几种低分子量萜烯进行了合适的分析。这些是为橄榄油行业的固体废物增值的有趣过程。
• Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis
  作者：Andrés Garcı́a-Granados、Pilar E López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1016/j.tet.2004.03.008

  日期：2004.4

  An exhaustive oxidation study has been made with ozone, MCPBA and/or NaIO4/RuCl3 of several triterpenic diene and triene compounds from oleanolic and maslinic acids obtained from olive-oil pressing. Through several oxidative cleavages of the opened C-ring of these oleantrienes, different significant decalin-type chiral synthons were achieved. These sesquiterpene and nor-sesquiterpene products are of great interest because by means of several simple reactions they could lead to drimane, phenanthrene and tricyclic triterpene compounds. (C) 2004 Elsevier Ltd. All rights reserved.
• Degradation of triterpenic compounds from olive-pressing residues. Synthesis of trans-decalin type chiral synthons
  作者：Andrés Garcı́a-Granados、Pilar E López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1016/s0040-4039(03)01634-4

  日期：2003.8

  Three seco-Gring triterpenic compounds were obtained from oleanolic or maslinic acids from olive-mill solid wastes by photochemical and chemical reactions. From these oleantriene compounds, different remarkable sesquiterpene and nor-sesquiterpene fragments such as 3beta-hydroxydrimenol (13) and epoxydecalone (16) were achieved through oxidative cleavages of the double bonds in the opened Gring. (C) 2003 Published by Elsevier Ltd.
• Reactivity of Chiral Sesquiterpene Synthons Obtained by the Degradation of Maslinic Acid from Olive‐Pressing Residues
  作者：Andrés Garcia‐Granados、Pilar E. López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1080/00397910600773858

  日期：2006.10

  Maslinic acid, a naturally occurring compound isolated from the solid wastes of olive-oil pressing, was fragmented through the C-ring via oxidative procedures to obtain two structural fragments. The chemical behaviors of cis-decalin, from the D and E rings, and of trans-decalin fragments, from the A and B rings, were investigated in depth using several chemical and enzymatic reactions. These decalin chiral synthons are interesting intermediates to semisynthesize phenanthrene- and drimane-type compounds and natural tricyclic triterpenes.