(1S,4aR,6S,8aS)-1,6-dimethyl-2-oxo-4a,5,6,7,8,8a-hexahydronaphthalene-1-carbaldehyde | 1239915-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,4aR,6S,8aS)-1,6-dimethyl-2-oxo-4a,5,6,7,8,8a-hexahydronaphthalene-1-carbaldehyde
• CAS: 1239915-89-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: OLFPDYQSMMFVHB-MRBYEJRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4aR,6S,8aS)-1,6-dimethyl-2-oxo-4a,5,6,7,8,8a-hexahydronaphthalene-1-carbaldehyde 在 tetra-n-propylammonium perruthenate. 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-[(1R,2R,4aR,6S,8aS)-2-hydroxy-1,2,6-trimethyl-4a,5,6,7,8,8a-hexahydronaphthalen-1-yl]ethanone
  参考文献：
  名称：

  An Efficient Access to Aspermytin A and Oblongolide C through an Intramolecular Nitrile Oxide–Alkene [3+2] Cycloaddition

  摘要：

  The second generation synthesis of (+)-aspermytin A and the first total synthesis of (-)-oblongolide C have been accomplished employing an intramolecular nitrile oxide-alkene [3+2] cycloaddition as the key step.

  DOI：

  10.1055/s-0032-1317693
• 作为产物：
  描述：

  [(1S,4aR,6S,8aS)-1,6-dimethyl-2-trimethylsilyloxy-4a,5,6,7,8,8a-hexahydro-4H-naphthalen-1-yl]methoxy-trimethylsilane 在 IBX*4-methoxypyridine-N-oxide complex 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 10.0h， 以58%的产率得到(1S,4aR,6S,8aS)-1,6-dimethyl-2-oxo-4a,5,6,7,8,8a-hexahydronaphthalene-1-carbaldehyde
  参考文献：
  名称：

  An Efficient Access to Aspermytin A and Oblongolide C through an Intramolecular Nitrile Oxide–Alkene [3+2] Cycloaddition

  摘要：

  The second generation synthesis of (+)-aspermytin A and the first total synthesis of (-)-oblongolide C have been accomplished employing an intramolecular nitrile oxide-alkene [3+2] cycloaddition as the key step.

  DOI：

  10.1055/s-0032-1317693

文献信息

• Total synthesis of (+)-aspermytin A
  作者：Atsushi Inoue、Makoto Kanematsu、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tetlet.2010.05.107

  日期：2010.7

  The first enantioselective total synthesis of aspermytin A, a new neurotrophic polyketide isolated from a cultured marine fungus of the genus Aspergillus sp., has been accomplished in 24 steps with an overall yield of 9.7% from S-(-)-citronellal. (C) 2010 Elsevier Ltd. All rights reserved.
• An Efficient Access to Aspermytin A and Oblongolide C through an Intramolecular Nitrile Oxide–Alkene [3+2] Cycloaddition
  作者：Kozo Shishido、Atsushi Inoue、Makoto Kanematsu、Seiji Mori、Masahiro Yoshida

  DOI：10.1055/s-0032-1317693

  日期：——

  The second generation synthesis of (+)-aspermytin A and the first total synthesis of (-)-oblongolide C have been accomplished employing an intramolecular nitrile oxide-alkene [3+2] cycloaddition as the key step.