(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,8,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal | 10528-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,8,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal
• 英文别名: 2-Aethandiyldioxy-1r-hydroxymethyl-5,5,8ac-trimethyl-decalin；[(1'S,4'aS,8'aS)-5',5',8'a-trimethylspiro[1,3-dioxolane-2,2'-3,4,4a,6,7,8-hexahydro-1H-naphthalene]-1'-yl]methanol
• CAS: 10528-17-3
• 化学式: C₁₆H₂₈O₃
• 分子量: 268.397
• InChiKey: CMXYUYVLPBNZPX-GUTXKFCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,8,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal 在 溶剂黄146 作用下， 反应 1.0h， 生成 (-)-(1S,4aS,8aS)-1α,2,3,4,4aα,5,6,7,8,8aα-decahydro-1β-hydroxymethyl-5,5,8aβ-trimethyl-2-oxonaphthalene
  参考文献：
  名称：

  Taniguchi, Makoto; Adachi, Takeshi; Oi, Susumu, Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 73 - 78

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Aethandiyldioxy-5,5,8ac-trimethyl-decalin-1r-carbonsaeure-methylester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,8,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal
  参考文献：
  名称：

  Taniguchi, Makoto; Adachi, Takeshi; Oi, Susumu, Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 73 - 78

  摘要：

  DOI：

文献信息

• Chemoenzymatic synthesis of (+)-totarol, (+)-podototarin, (+)-sempervirol, and (+)-jolkinolides E and D
  作者：Takahiro Miyake、Hideo Kigoshi、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2007.11.024

  日期：2007.12

  The enzymatic resolution products [(1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-7 (98% ee) and acetate of (IS,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal} (8aS)-9 (>99% ee)] obtained by the lipase-catalyzed enantioselective acetylation of (+/-)-7 in the presence of vinyl acetate as an acyl donor were converted to the alpha,beta-unsaturated ketones (8aR)-6 and (8aS)-6, respectively. Concise syntheses of (+)-totarol 1, (+)-podototarin 2 and (+)-sempervirol 3 were achieved based on Michael reactions between (8aS)-6 and the appropriate P-keto ester followed by aldol condensation. The first chiral syntheses of (+)-jolkinolides E 4 and D 5 were achieved from (5R,10R,12R)-12-hydroxypodocarpa-8(14)-en-13-one 15 derived from (8aR)-6. (c) 2007 Elsevier Ltd. All rights reserved.
• Taniguchi, Makoto; Adachi, Takeshi; Oi, Susumu, Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 73 - 78
  作者：Taniguchi, Makoto、Adachi, Takeshi、Oi, Susumu、Kimura, Akihiko、Katsumura, Shigeo、et al.

  DOI：——

  日期：——