(1R,2R,4aR,7R,8aR)-1,4a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl methanesulfonate | 198994-38-6

• 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: (1R,2R,4aR,7R,8aR)-1,4a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl methanesulfonate
• 英文别名: [(1R,2R,4aR,7R,8aR)-1,4a-dimethyl-7-prop-1-en-2-yl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl] methanesulfonate
• CAS: 198994-38-6
• 化学式: C₁₆H₂₈O₃S
• 分子量: 300.463
• InChiKey: VXCVKVCEGYBUHJ-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R,4aR,7R,8aR)-1,4a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl methanesulfonate 在 Pd/SrCO₃ 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 bis(acetylacetonate)oxovanadium 、 氢气 、 aluminum isopropoxide 、 lithium carbonate 、 间氯过氧苯甲酸 、 lithium bromide 作用下， 以 吡啶 、 乙醚 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 反应 37.5h， 生成 臭灵丹二醇
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-7βH-Eudesmane-4α,11-diol and (+)-ent-7βH-Eudesmane-4α,11-diol

  摘要：

  The syntheses of (-)-7 beta H-eudesmane-4 alpha,11-diol (2) and (+)-ent-7 beta H-eudesmane-4 alpha,11-diol (ent-2) were carried out starting from (-)- and (+)-dihydrocarvones. As a result, the structure, including absolute configuration, of the naturally occurring eudesmane-4,11-diol isolated from Pluchea arguta was determined to be (+)-ent-7 beta H-eudesmane-4 alpha,11-diol (ent-2).

  DOI：

  10.1021/np9702906
• 作为产物：
  描述：

  (1R,4aR,7R,8aR)-8a-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-octahydronaphthalen-2(1H)-one 在 盐酸 、 sodium tetrahydroborate 、 乙醇 、 氨 、 lithium 作用下， 以 吡啶 、 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 12.83h， 生成 (1R,2R,4aR,7R,8aR)-1,4a-dimethyl-7-(prop-1-en-2-yl)-decahydronaphthalen-2-yl methanesulfonate
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-7βH-Eudesmane-4α,11-diol and (+)-ent-7βH-Eudesmane-4α,11-diol

  摘要：

  The syntheses of (-)-7 beta H-eudesmane-4 alpha,11-diol (2) and (+)-ent-7 beta H-eudesmane-4 alpha,11-diol (ent-2) were carried out starting from (-)- and (+)-dihydrocarvones. As a result, the structure, including absolute configuration, of the naturally occurring eudesmane-4,11-diol isolated from Pluchea arguta was determined to be (+)-ent-7 beta H-eudesmane-4 alpha,11-diol (ent-2).

  DOI：

  10.1021/np9702906

文献信息

• Stereoselective synthesis of (–)-4-epiaxinyssamine
  作者：Leonardo Castellanos、Carmenza Duque、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1016/j.tet.2006.12.019

  日期：2007.2

  The synthetic studies towards axinyssamine, a cytotoxic and coral-lethal compound isolated from the Caribbean sponge Axinyssa ambrosia were performed. The Ritter reaction on the key intermediate with chloroacetonitrile, resulted in the introduction of the amino group at C-4 generating the configuration of this stereocentre opposite to that of the natural product. As a result, the first total synthesis of the unnatural (-)-4-epiaxinyssamine was achieved. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantioselective Total Syntheses of (−)-7β<i>H</i>-Eudesmane-4α,11-diol and (+)-<i>ent</i>-7β<i>H</i>-Eudesmane-4α,11-diol
  作者：Fumito Shimoma、Hisao Kondo、Saori Yuuya、Toshio Suzuki、Hisahiro Hagiwara、Masayoshi Ando

  DOI：10.1021/np9702906

  日期：1998.1.1

  The syntheses of (-)-7 beta H-eudesmane-4 alpha,11-diol (2) and (+)-ent-7 beta H-eudesmane-4 alpha,11-diol (ent-2) were carried out starting from (-)- and (+)-dihydrocarvones. As a result, the structure, including absolute configuration, of the naturally occurring eudesmane-4,11-diol isolated from Pluchea arguta was determined to be (+)-ent-7 beta H-eudesmane-4 alpha,11-diol (ent-2).