2-(5-hydroxypentyl)-3-methyl-2-cyclopenten-1-one | 1093945-44-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(5-hydroxypentyl)-3-methyl-2-cyclopenten-1-one
• 英文别名: 2-(5-Hydroxypentyl)-3-methylcyclopent-2-en-1-one；2-(5-hydroxypentyl)-3-methylcyclopent-2-en-1-one
• CAS: 1093945-44-8
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: SIJWYRFEBIXBIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-hydroxypentyl)-3-methyl-2-cyclopenten-1-one 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以100%的产率得到5-(2-methyl-5-oxo-1-cyclopenten-1-yl)pentanal
  参考文献：
  名称：

  Preparation of seven- and eight-membered rings by carbon–carbon bond formation induced by samarium diiodide: 7-endo- and 8-endo-trig type cyclization to bicyclo[5.3.0]decanolone, bicyclo[5.4.0]undecanolone, and bicyclo[6.4.0]dodecanolone

  摘要：

  Compounds with an enone-aldehyde/ketone were treated with Sml(2) to form the bicyclic ketols, bicyclo[5.3.0]decanolones, and bicyclo[5.4.0]undecanolones, in different ratios depending on the reaction conditions (with or without different amounts of additives, low temperature or rt). The tendency to form seven-membered rings was different from that of six-membered rings and the mechanisms for these reactions are proposed. Cyclization to an eight-membered ring was attempted realizing in the yield of 26%. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.073
• 作为产物：
  描述：

  3-methyl-2-(5-tert-butyldimethylsilyloxypentyl)-2-cyclopenten-1-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到2-(5-hydroxypentyl)-3-methyl-2-cyclopenten-1-one
  参考文献：
  名称：

  Preparation of seven- and eight-membered rings by carbon–carbon bond formation induced by samarium diiodide: 7-endo- and 8-endo-trig type cyclization to bicyclo[5.3.0]decanolone, bicyclo[5.4.0]undecanolone, and bicyclo[6.4.0]dodecanolone

  摘要：

  Compounds with an enone-aldehyde/ketone were treated with Sml(2) to form the bicyclic ketols, bicyclo[5.3.0]decanolones, and bicyclo[5.4.0]undecanolones, in different ratios depending on the reaction conditions (with or without different amounts of additives, low temperature or rt). The tendency to form seven-membered rings was different from that of six-membered rings and the mechanisms for these reactions are proposed. Cyclization to an eight-membered ring was attempted realizing in the yield of 26%. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.073

文献信息

• Preparation of seven- and eight-membered rings by carbon–carbon bond formation induced by samarium diiodide: 7-endo- and 8-endo-trig type cyclization to bicyclo[5.3.0]decanolone, bicyclo[5.4.0]undecanolone, and bicyclo[6.4.0]dodecanolone
  作者：Masakazu Sono、Yuri Sugimoto、Hiroyuki Tatara、Natsuko Ise、Shigeru Takaoka、Motoo Tori

  DOI：10.1016/j.tet.2008.09.073

  日期：2008.12

  Compounds with an enone-aldehyde/ketone were treated with Sml(2) to form the bicyclic ketols, bicyclo[5.3.0]decanolones, and bicyclo[5.4.0]undecanolones, in different ratios depending on the reaction conditions (with or without different amounts of additives, low temperature or rt). The tendency to form seven-membered rings was different from that of six-membered rings and the mechanisms for these reactions are proposed. Cyclization to an eight-membered ring was attempted realizing in the yield of 26%. (C) 2008 Elsevier Ltd. All rights reserved.