(-)-1,1-bis(phenylsulphonyl)-4-(1-ethoxy-methylethyl)-3-methylene-cyclopentane | 1133733-74-0

• 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: (-)-1,1-bis(phenylsulphonyl)-4-(1-ethoxy-methylethyl)-3-methylene-cyclopentane
• CAS: 1133733-74-0
• 化学式: C₂₃H₂₈O₅S₂
• 分子量: 448.604
• InChiKey: DULNJVLAQHBYDJ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  77.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  乙醇 、 4,4-bis(phenylsulfonyl)-7-methyl-6-octen-1-yne 在 gold(III) chloride 、 silver hexafluoroantimonate 、 (S)-DTBM-MeOBIPHEP 作用下， 反应 24.0h， 生成 (+)-1,1-bis(phenylsulphonyl)-4-(1-hydroxy-methylethyl)-3-methylene-cyclopentane 、 (-)-1,1-bis(phenylsulphonyl)-4-(1-ethoxy-methylethyl)-3-methylene-cyclopentane
  参考文献：
  名称：

  Towards asymmetric Au-catalyzed hydroxy- and alkoxycyclization of 1,6-enynes

  摘要：

  The efficiency of a Au(III)/chiral ligand system has been studied. The association of several chiral mono- and bidentate phosphanes with gold has been tested in the formal addition of an oxygen nucleophile to an alkene followed by a cyclization process, namely the hydroxycyclization reaction of 1,6-enynes. The use of ( R)-4-MeO-3,5-(t-Bu)(2)-MeOBIPHEP ligand led to clean cycloisomerizations and afforded the highest enantiomeric excesses. The enantiomeric excesses were highly dependant on the substrate/nucleophile combination. A P-31 NMR study of the catalytic species tends to prove that Au( III) catalyst may be reduced to Au( I) intermediate in the presence of phosphanes. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.08.008