1H-cyclopenta[a]inden-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1H-cyclopenta[a]inden-2-one
• 英文别名: 1H-cyclopent[a]inden-2-one；Cyclopenta[a]inden-2-one；3H-cyclopenta[a]inden-2-one
• 化学式: C₁₂H₈O
• 分子量: 168.195
• InChiKey: BQWBQPUKFJHMAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1H-cyclopenta[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78%的产率得到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：

  1-乙炔基-2-丙二烯基苯 、 alkaline earth salt of/the/ methylsulfuric acid 以 二甲基亚砜 、 甲苯 为溶剂， 反应 8.0h， 以70%的产率得到1H-cyclopenta[a]inden-2-one
  参考文献：
  名称：

  Molybdenum-mediated cyclocarbonylation of 1-ethynyl-2-allenylbenzenes to 1H-cyclopenta[a]inden-2-ones

  摘要：

  Although 1-ethynyl-2-allenylbenzenes readily undergo Myers-Saito or Schmittel cyclization under mild conditions, cyclocarbonylation of these moieties to 1H-cyclopenta[a]inden-2-ones proceeds smoothly using suitable molybdenum carbonyl reagents, with Mo(CO)(3)(CH3CN)(3) being the most efficient. The yields of desired bicyclic ketones were up to 87-93%. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.068

文献信息

• Molybdenum-mediated cyclocarbonylation of 1-ethynyl-2-allenylbenzenes to 1H-cyclopenta[a]inden-2-ones
  作者：Swarup Datta、Rai-Shung Liu

  DOI：10.1016/j.tetlet.2005.09.068

  日期：2005.11

  Although 1-ethynyl-2-allenylbenzenes readily undergo Myers-Saito or Schmittel cyclization under mild conditions, cyclocarbonylation of these moieties to 1H-cyclopenta[a]inden-2-ones proceeds smoothly using suitable molybdenum carbonyl reagents, with Mo(CO)(3)(CH3CN)(3) being the most efficient. The yields of desired bicyclic ketones were up to 87-93%. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.