(1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-vinyl-decahydro-naphthalene-1-carboxylic acid methyl ester | 391277-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-vinyl-decahydro-naphthalene-1-carboxylic acid methyl ester
• CAS: 391277-72-8
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: CMCZIRCJZUHGNW-DTZQCDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-vinyl-decahydro-naphthalene-1-carboxylic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 15.5h， 生成 (1R,4aR,8S,8aR,10aS)-8-(4-Bromo-benzoyloxymethyl)-1,4a,8-trimethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester
  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：

  methyl (1R,4aR,8aS)-1,4a-dimethyl-5-oxo-3,4,6,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate 在 Lindlar's catalyst 氢气 作用下， 以 1,4-二氧六环 、 吡啶 、 乙醚 为溶剂， 反应 1.17h， 生成 (1R,4aR,5S,8aS)-5-Hydroxy-1,4a-dimethyl-5-vinyl-decahydro-naphthalene-1-carboxylic acid methyl ester
  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