3-epi-characiol | 1160699-98-8

• 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: 3-epi-characiol
• 英文别名: (1R,2S,3aR,5E,12E,13aS)-1,3a-dihydroxy-2,5,8,8,12-pentamethyl-2,3,7,10,11,13a-hexahydro-1H-cyclopenta[12]annulene-4,9-dione
• CAS: 1160699-98-8
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: LONPPGZUMORYRY-QTKCZRBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-epi-characiol 在 甲醇 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 characiol
  参考文献：
  名称：

  Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators

  摘要：

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

  DOI：

  10.1021/jo1019738
• 作为产物：
  描述：

  (1E)-1-[(1S,2R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-4-methyl-2-(2-methylprop-2-enoyl)cyclopentyl]-2,6,6-trimethylnona-1,8-dien-5-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 氟化氢吡啶 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 3.42h， 以44%的产率得到3-epi-characiol
  参考文献：
  名称：

  Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

  摘要：

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.

  DOI：

  10.1021/ol900819u