methyl (1R,4aR,5S,8aS)-5-ethynyl-5-hydroxy-1,4a-dimethyl-3,4,6,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate | 287401-10-9

• 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: methyl (1R,4aR,5S,8aS)-5-ethynyl-5-hydroxy-1,4a-dimethyl-3,4,6,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 287401-10-9
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: VXOPLXCSUKPZCT-DTZQCDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1R,4aR,5S,8aS)-5-ethynyl-5-hydroxy-1,4a-dimethyl-3,4,6,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate 在 Lindlar's catalyst sodium tetrahydroborate 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 苯 为溶剂， 反应 13.67h， 生成 methyl (1R,4aR,8S,8aR,10aS)-8-(hydroxymethyl)-1,4a,8-trimethyl-3,4,6,7,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of (−)-Acanthoic Acid

  摘要：

  GRAPHICSThe first stereoselective synthesis of (-)-acanthoic acid (1) has been designed and accomplished. Our synthetic plan departs from (-) Wieland-Miesher ketone (7) and calls upon a Diels-Alder cycloaddition reaction for the construction of the C ring of 1. The described synthesis confirms the proposed stereochemistry of 1 and represents an efficient entry into an unexplored class of biologically active diterpenes.

  DOI：

  10.1021/ol0060578
• 作为产物：
  描述：

  (4'aR,5'R,8'aR)-3',4',6',7',8',8'alpha-六氢-8'alpha-甲基-6'-氧代-螺[1,3-二氧戊环-2,1'(2'H)-萘]-5'-羧酸甲酯 在 盐酸 、 氨 、 lithium 、 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 为溶剂， 反应 7.58h， 生成 methyl (1R,4aR,5S,8aS)-5-ethynyl-5-hydroxy-1,4a-dimethyl-3,4,6,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of (−)-Acanthoic Acid

  摘要：

  GRAPHICSThe first stereoselective synthesis of (-)-acanthoic acid (1) has been designed and accomplished. Our synthetic plan departs from (-) Wieland-Miesher ketone (7) and calls upon a Diels-Alder cycloaddition reaction for the construction of the C ring of 1. The described synthesis confirms the proposed stereochemistry of 1 and represents an efficient entry into an unexplored class of biologically active diterpenes.

  DOI：

  10.1021/ol0060578