(1S,3R,3aS,6aR)-1,3-Diphenethyl-1,3,3a,6a-tetrahydro-cyclopenta[c]furan-4-one | 868696-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,3R,3aS,6aR)-1,3-Diphenethyl-1,3,3a,6a-tetrahydro-cyclopenta[c]furan-4-one
• 英文别名: (1S,3R,3aS,6aR)-1,3-bis(2-phenylethyl)-1,3,3a,6a-tetrahydrocyclopenta[c]furan-4-one
• CAS: 868696-86-0
• 化学式: C₂₃H₂₄O₂
• 分子量: 332.442
• InChiKey: XELWHXVYPLUNRO-KZKAQZJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R,3aS,6aR)-1,3-Diphenethyl-1,3,3a,6a-tetrahydro-cyclopenta[c]furan-4-one 在 copper(l) iodide 、 1,4-环己二烯 、 diethylzinc 、 ferric nitrate 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (1S,3R,3aS,7R,7aR)-7-Isopropyl-1,3-diphenethyl-hexahydro-isobenzofuran-4-one
  参考文献：
  名称：

  Stereoselective synthesis of the octahydroisobenzofuran skeleton of the eunicellins

  摘要：

  A de novo asymmetric synthesis of the octahydroisobenzofuran skeleton contained within the eunicellin family of natural products has been completed. The key transformations involve the convergent assembly of a tetrasubstituted tetrahydrofuran by condensation of a functionalised allylsiloxane with an aldehyde; controlled epimerisation of a C4 aldehyde by intramolecular trapping; installation of the isopropyl substituent by stereoselective Michael addition to a 5,5-bicyclic enone; and ring expansion of the 5,5-system to the target structure by radical-mediated cyclopropane fragmentation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.046
• 作为产物：
  描述：

  (2S,3S,4R,5R)-4-Hydroxymethyl-2,5-diphenethyl-tetrahydro-furan-3-carbaldehyde 在 Grubbs catalyst first generation 、 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (1S,3R,3aS,6aR)-1,3-Diphenethyl-1,3,3a,6a-tetrahydro-cyclopenta[c]furan-4-one
  参考文献：
  名称：

  Stereoselective synthesis of the octahydroisobenzofuran skeleton of the eunicellins

  摘要：

  A de novo asymmetric synthesis of the octahydroisobenzofuran skeleton contained within the eunicellin family of natural products has been completed. The key transformations involve the convergent assembly of a tetrasubstituted tetrahydrofuran by condensation of a functionalised allylsiloxane with an aldehyde; controlled epimerisation of a C4 aldehyde by intramolecular trapping; installation of the isopropyl substituent by stereoselective Michael addition to a 5,5-bicyclic enone; and ring expansion of the 5,5-system to the target structure by radical-mediated cyclopropane fragmentation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.046

文献信息

• Stereoselective synthesis of the octahydroisobenzofuran skeleton of the eunicellins
  作者：Tito Akindele、Stephen P. Marsden、John G. Cumming

  DOI：10.1016/j.tetlet.2005.08.046

  日期：2005.10

  A de novo asymmetric synthesis of the octahydroisobenzofuran skeleton contained within the eunicellin family of natural products has been completed. The key transformations involve the convergent assembly of a tetrasubstituted tetrahydrofuran by condensation of a functionalised allylsiloxane with an aldehyde; controlled epimerisation of a C4 aldehyde by intramolecular trapping; installation of the isopropyl substituent by stereoselective Michael addition to a 5,5-bicyclic enone; and ring expansion of the 5,5-system to the target structure by radical-mediated cyclopropane fragmentation. (c) 2005 Elsevier Ltd. All rights reserved.