5-(2-methyl-5-oxo-1-cyclopenten-1-yl)pentanal | 1093945-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2-methyl-5-oxo-1-cyclopenten-1-yl)pentanal
• 英文别名: 5-(2-Methyl-5-oxocyclopenten-1-yl)pentanal；5-(2-methyl-5-oxocyclopenten-1-yl)pentanal
• CAS: 1093945-16-4
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: GUDBJFDDOAMODT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-methyl-5-oxo-1-cyclopenten-1-yl)pentanal 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到(8aS)-4-hydroxy-3a-methyl-2,3,4,5,6,7,8,8a-octahydroazulen-1-one
  参考文献：
  名称：

  Neodolastanes 的研究 — trichoaurantianolides 的三环核心的合成

  摘要：

  描述了对 trichoaurantianolide C (5) 合成的研究。(E)- 和 (Z)-β-甲锡烷基-α,β-不饱和酯与乙酸烯丙酯 32 的 Stille 交叉偶联反应提供了非共轭 2,5-二烯-1-醇的立体控制形成。利用对不对称 Sharpless 环氧化的研究来建立非对映选择性，以制备用于随后酯化和闭环复分解的关键 C2 叔烯丙醇。关键丁烯内酯前体 49 的 SmI2 还原环化导致天然产物三环核心的中心七元环的形成。

  DOI：

  10.1139/v2012-088
• 作为产物：
  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

文献信息

• Studies of neodolastanes — Synthesis of the tricyclic core of the trichoaurantianolides
  作者：David R. Williams、Joseph R. Pinchman

  DOI：10.1139/v2012-088

  日期：2013.1

  the synthesis of trichoaurantianolide C (5) are described. Stille cross-coupling reactions of (E)- and (Z)-β-stannyl-α,β-unsaturated esters with allylic acetate 32 provide for the stereocontrolled formation of nonconjugated 2,5-diene-1-ols. Studies of the asymmetric Sharpless epoxidation are utilized to establish diastereofacial selectivity for the preparation of a crucial C2 tertiary allylic alcohol

  描述了对 trichoaurantianolide C (5) 合成的研究。(E)- 和 (Z)-β-甲锡烷基-α,β-不饱和酯与乙酸烯丙酯 32 的 Stille 交叉偶联反应提供了非共轭 2,5-二烯-1-醇的立体控制形成。利用对不对称 Sharpless 环氧化的研究来建立非对映选择性，以制备用于随后酯化和闭环复分解的关键 C2 叔烯丙醇。关键丁烯内酯前体 49 的 SmI2 还原环化导致天然产物三环核心的中心七元环的形成。
• 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.