[(1S,11R,12R)-8-(benzenesulfonyl)-13-oxatetracyclo[7.4.0.01,12.02,7]trideca-2,4,6,8-tetraen-11-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1173722-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: [(1S,11R,12R)-8-(benzenesulfonyl)-13-oxatetracyclo[7.4.0.01,12.02,7]trideca-2,4,6,8-tetraen-11-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1173722-70-7
• 化学式: C₂₈H₂₁F₃O₆S
• 分子量: 542.532
• InChiKey: HFTSYLFSXCRGDW-STAKNXPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2R,3R,3aS)-3,3a-epoxy-8-(phenylsulfonyl)-1,2,3,3a-tetrahydrocyclopent[a]inden-2-ol 、 甲氧基-三氟甲基苯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到[(1S,11R,12R)-8-(benzenesulfonyl)-13-oxatetracyclo[7.4.0.01,12.02,7]trideca-2,4,6,8-tetraen-11-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Synthesis of a Core Carbon Framework of Cyanosporasides A and B

  摘要：

  Treatment of 3-(2-ethynylphenyl)prop-2-ynyl benzenesulfinate with 2.5-mol % of [RhCl(CO)(2)](2) at 40 degrees C under an atmosphere of CO effected the successive 2,3-sigmatropic rearrangement and carbonylative [2 + 2 + 1] ring-closing reaction to afford the 8-(phenylsulfonyl)-1H-cyclopent[a]-inden-2-one in a high yield. Chemical modification of the ring-closed product via lipase-mediated optical resolution produced tile optically active 3-acetoxy-3a-cyclohexyloxy-3,3a-dihydrocyclopent[a]indene skeleton, the core carbon framework of cyanosporasides A and B.

  DOI：

  10.1021/jo901141t

文献信息

• Synthesis of a Core Carbon Framework of Cyanosporasides A and B
  作者：Daisuke Aburano、Fuyuhiko Inagaki、Shoichirou Tomonaga、Chisato Mukai

  DOI：10.1021/jo901141t

  日期：2009.8.7

  Treatment of 3-(2-ethynylphenyl)prop-2-ynyl benzenesulfinate with 2.5-mol % of [RhCl(CO)(2)](2) at 40 degrees C under an atmosphere of CO effected the successive 2,3-sigmatropic rearrangement and carbonylative [2 + 2 + 1] ring-closing reaction to afford the 8-(phenylsulfonyl)-1H-cyclopent[a]-inden-2-one in a high yield. Chemical modification of the ring-closed product via lipase-mediated optical resolution produced tile optically active 3-acetoxy-3a-cyclohexyloxy-3,3a-dihydrocyclopent[a]indene skeleton, the core carbon framework of cyanosporasides A and B.