(1R,2S,7a'R)-(+)-1,7,7,7a'-tetramethyl-7',7a'-dihydro-1'H-spiro[bicyclo[2.2.1]heptane-2,3'-cyclopenta[c]pyran]-6'(4'H)-one | 1132772-02-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,7a'R)-(+)-1,7,7,7a'-tetramethyl-7',7a'-dihydro-1'H-spiro[bicyclo[2.2.1]heptane-2,3'-cyclopenta[c]pyran]-6'(4'H)-one
• 英文别名: (1'R,3S,4'R,7aR)-1',7',7',7a-tetramethylspiro[4,7-dihydro-1H-cyclopenta[c]pyran-3,2'-bicyclo[2.2.1]heptane]-6-one
• CAS: 1132772-02-1
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: PCTNKVKKBPLKSO-IUHNQTRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2S)-(-)-1,7,7-trimethyl-2-(2-methylallyl)-2-(prop-2-ynyloxy)bicyclo[2.2.1]heptane 在 dicobalt octacarbonyl 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以82%的产率得到(1R,2S,7a'R)-(+)-1,7,7,7a'-tetramethyl-7',7a'-dihydro-1'H-spiro[bicyclo[2.2.1]heptane-2,3'-cyclopenta[c]pyran]-6'(4'H)-one
  参考文献：
  名称：

  Stereoselective synthesis of spirocyclic cyclopentapyrans by the Pauson–Khand reaction on camphor tethered enynes

  摘要：

  An intramolecular Pauson-Khand reaction of camphor tethered enynes derived from homoallyl, homomethallyl and homopropargyl alcohols is described. Homoallyl, homomethallyl, and homopropargyl moieties are easily constructed on the camphor carbonyl group with excellent diastereoselectivity due to endo-face selectivity, and with known stereochemistry. Each enantiomerically pure enyne affords the conformationally most stable diastereomeric spirocyclic cyclopenta[c]pyran ring system. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.020

文献信息

• Stereoselective synthesis of spirocyclic cyclopentapyrans by the Pauson–Khand reaction on camphor tethered enynes
  作者：Serdar Sezer、Yasemin Gümrükçü、Ertan Şahin、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2008.11.020

  日期：2008.12

  An intramolecular Pauson-Khand reaction of camphor tethered enynes derived from homoallyl, homomethallyl and homopropargyl alcohols is described. Homoallyl, homomethallyl, and homopropargyl moieties are easily constructed on the camphor carbonyl group with excellent diastereoselectivity due to endo-face selectivity, and with known stereochemistry. Each enantiomerically pure enyne affords the conformationally most stable diastereomeric spirocyclic cyclopenta[c]pyran ring system. (C) 2008 Elsevier Ltd. All rights reserved.