(4R*,5R*)-3-(ethoxycarbonyl)-4-n-hexyl-2-phenyl-5-<(phenylsulfonyl)methyl>-4,5-dihydrofuran

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4R*,5R*)-3-(ethoxycarbonyl)-4-n-hexyl-2-phenyl-5-<(phenylsulfonyl)methyl>-4,5-dihydrofuran
• 英文别名: ethyl (2S,3S)-2-(benzenesulfonylmethyl)-3-hexyl-5-phenyl-2,3-dihydrofuran-4-carboxylate
• 化学式: C₂₆H₃₂O₅S
• 分子量: 456.603
• InChiKey: AZFRXLCYCNICHH-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-1-phenylsulfonyl-1-nonen-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (4R*,5R*)-3-(ethoxycarbonyl)-4-n-hexyl-2-phenyl-5-<(phenylsulfonyl)methyl>-4,5-dihydrofuran
  参考文献：
  名称：

  Palladium-Catalyzed Allylic Substitution in γ-Oxygenated Vinyl Sulfones:  One-Step Synthesis of Tetrasubstituted Dihydrofurans

  摘要：

  DOI：

  10.1021/jo970864b

文献信息

• Palladium-Catalyzed Allylic Substitution in γ-Oxygenated Vinyl Sulfones:  One-Step Synthesis of Tetrasubstituted Dihydrofurans
  作者：Inés Alonso、Juan C. Carretero、Jose L. Garrido、Virginia Magro、Concepción Pedregal

  DOI：10.1021/jo970864b

  日期：1997.8.1
• One-Step Palladium-Catalyzed Synthesis of Substituted Dihydrofurans from the Carbonate Derivatives of γ-Hydroxy-α,β-unsaturated Sulfones
  作者：José L. Garrido、Inés Alonso、Juan C. Carretero

  DOI：10.1021/jo981391r

  日期：1998.12.1

  The palladium-catalyzed nucleophilic allylic substitution of the carbonate derivatives of gamma-hydroxy-alpha,beta-unsaturated sulfones (2) with soft carbon nucleophiles such as malonates, beta-keto esters, 1,3-diketones, and alpha-sulfonyl ketones took place cleanly and with full regiocontrol (gamma-substitution). Typical optimized conditions are Pd-2(dba)(3) (5 mol %), dppe (20 mol %), molecular sieves, in toluene-THF at 100 degrees C. Unexpectedly, when beta-keto esters, 1,3-diketones, and alpha-sulfonyl ketones were used as nucleophiles a cascade process occurred, via initial gamma-regioselective allylic substitution and further intramolecular conjugate addition of the enol moiety to the alpha,beta-unsaturated sulfone, to give 2,3,4,5-tetrasubstituted dihydrofurans (13-25) in moderate to good yields. Moreover, the cyclization step is highly stereoselective giving predominantly or exclusively the 4,5-dihydrofuran of trans configuration. From readily available enantiopure (S)-2, this one-step procedure of synthesis of substituted dihydrofurans has been applied to the synthesis of enantiomerically pure tetrasubstituted tetrahydrofurans.