8-(phenylsulfonyl)-1H-cyclopent[a]inden-2-one | 1173722-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 8-(phenylsulfonyl)-1H-cyclopent[a]inden-2-one
• 英文别名: 4-(benzenesulfonyl)-3H-cyclopenta[a]inden-2-one
• CAS: 1173722-49-0
• 化学式: C₁₈H₁₂O₃S
• 分子量: 308.357
• InChiKey: XAGUMNMNLJGJSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(phenylsulfonyl)-1H-cyclopent[a]inden-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以64%的产率得到8-(phenylsulfonyl)-1,2-dihydrocyclopent[a]inden-2-ol
  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
• 作为产物：
  描述：

  一氧化碳 、 3-(2-ethynylphenyl)prop-2-ynyl benzenesulfinate 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 甲苯 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 以81%的产率得到8-(phenylsulfonyl)-1H-cyclopent[a]inden-2-one
  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.