(2S,3S,3aR,5aS,9aS,9bR)-3-((S)-2-Furan-3-yl-2-hydroxy-ethyl)-2,3a,6,6,9a-pentamethyl-dodecahydro-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester | 138355-09-6

• 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: (2S,3S,3aR,5aS,9aS,9bR)-3-((S)-2-Furan-3-yl-2-hydroxy-ethyl)-2,3a,6,6,9a-pentamethyl-dodecahydro-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S,3aR,5aS,9aS,9bR)-3-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-3,4,5,5a,7,8,9,9b-octahydro-1H-cyclopenta[a]naphthalene-2-carboxylate
• CAS: 138355-09-6
• 化学式: C₂₆H₄₀O₄
• 分子量: 416.601
• InChiKey: OTCLYBHZKVFHNN-KOJABWAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,3aR,5aS,9aS,9bR)-3-((S)-2-Furan-3-yl-2-hydroxy-ethyl)-2,3a,6,6,9a-pentamethyl-dodecahydro-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以0.5 mg的产率得到(2S,3S,3aR,5aS,9aS,9bR)-3-(2-Furan-3-yl-2-oxo-ethyl)-2,3a,6,6,9a-pentamethyl-dodecahydro-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Hyrtiosal, a new sesterterpenoid with a novel carbon skeleton from the Okinawan marine sponge Hyrtios erectus

  摘要：

  Hyrtiosal, a new sesterterpenoid possessing a novel rearranged tricarbocyclic skeleton, was isolated from the Okinawan marine sponge, Hyrtios erectus (Keller, 1891). This compound was shown to inhibit the proliferation of KB cells in vitro, and its structure was determined by chemical and spectral methods including two-dimensional C-13-H-1 long-range correlations. The relative stereochemistry was determined based on two-dimensional NOE correlations. A possible biosynthesis of hyrtiosal is briefly discussed.

  DOI：

  10.1021/jo00028a023
• 作为产物：
  描述：

  hyrtiosal 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 乙醚 、 叔丁醇 为溶剂， 反应 1.5h， 生成 (2S,3S,3aR,5aS,9aS,9bR)-3-((S)-2-Furan-3-yl-2-hydroxy-ethyl)-2,3a,6,6,9a-pentamethyl-dodecahydro-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Hyrtiosal, a new sesterterpenoid with a novel carbon skeleton from the Okinawan marine sponge Hyrtios erectus

  摘要：

  Hyrtiosal, a new sesterterpenoid possessing a novel rearranged tricarbocyclic skeleton, was isolated from the Okinawan marine sponge, Hyrtios erectus (Keller, 1891). This compound was shown to inhibit the proliferation of KB cells in vitro, and its structure was determined by chemical and spectral methods including two-dimensional C-13-H-1 long-range correlations. The relative stereochemistry was determined based on two-dimensional NOE correlations. A possible biosynthesis of hyrtiosal is briefly discussed.

  DOI：

  10.1021/jo00028a023