2-[(2R,4aS,8aR)-5,5,8a-trimethyl-3-oxo-2,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]acetic acid | 742068-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2R,4aS,8aR)-5,5,8a-trimethyl-3-oxo-2,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]acetic acid
• CAS: 742068-91-3
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: GRCWXZNYNSVKPB-ITDIGPHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-[(2R,4aS,8aR)-5,5,8a-trimethyl-3-oxo-2,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]acetic acid 在 sodium acetate 作用下， 以66%的产率得到(4aR,8aS,9aS)-4a,8,8-Trimethyl-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one
  参考文献：
  名称：

  The first synthesis and absolute configuration of glaucescenolide

  摘要：

  The first synthesis of glaucescenolide (1), a cytotoxic sesquiterpene isolated from the liverwort, Schistochila glaucescens, was achieved by starting from 2,2,6-trimethylcyclohexanone (2). The absolute configuration of the naturally occurring 1 was confirmed as 5S,7S,10R. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.148
• 作为产物：
  描述：

  [(2R,4aR)-4a,8,8-trimethyl-2,3,4,5,6,7-hexahydronaphthalen-2-yl] acetate 在 palladium on activated charcoal 六甲基磷酰三胺 、 manganese(IV) oxide 、 lithium hydroxide 、 氢气 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 为溶剂， 生成 2-[(2R,4aS,8aR)-5,5,8a-trimethyl-3-oxo-2,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl]acetic acid
  参考文献：
  名称：

  The first synthesis and absolute configuration of glaucescenolide

  摘要：

  The first synthesis of glaucescenolide (1), a cytotoxic sesquiterpene isolated from the liverwort, Schistochila glaucescens, was achieved by starting from 2,2,6-trimethylcyclohexanone (2). The absolute configuration of the naturally occurring 1 was confirmed as 5S,7S,10R. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.148

文献信息

• The first synthesis and absolute configuration of glaucescenolide
  作者：Hirosato Takikawa、Keiko Ueda、Mitsuru Sasaki

  DOI：10.1016/j.tetlet.2004.05.148

  日期：2004.7

  The first synthesis of glaucescenolide (1), a cytotoxic sesquiterpene isolated from the liverwort, Schistochila glaucescens, was achieved by starting from 2,2,6-trimethylcyclohexanone (2). The absolute configuration of the naturally occurring 1 was confirmed as 5S,7S,10R. (C) 2004 Elsevier Ltd. All rights reserved.