ethyl (E)-1-(phenylsulfonyl)-1-buten-3-yl carbonate | 194851-85-9

• 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: ethyl (E)-1-(phenylsulfonyl)-1-buten-3-yl carbonate
• 英文别名: [(E)-4-(benzenesulfonyl)but-3-en-2-yl] ethyl carbonate
• CAS: 194851-85-9
• 化学式: C₁₃H₁₆O₅S
• 分子量: 284.333
• InChiKey: XCKHIDROTMPAKI-MDZDMXLPSA-N

物化性质

• 沸点：
  431.5±45.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-1-(phenylsulfonyl)-1-buten-3-yl carbonate 在 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， 反应 28.0h， 生成 Ethyl 2-(benzenesulfonylmethyl)-3,5-dimethyl-2,3-dihydrofuran-4-carboxylate
  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
• 作为产物：
  描述：

  (E)-1-benzenesulfonyl-1-buten-3-ol 、 氯甲酸乙酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到ethyl (E)-1-(phenylsulfonyl)-1-buten-3-yl carbonate
  参考文献：
  名称：

  One-Step Palladium-Catalyzed Synthesis of Substituted Dihydrofurans from the Carbonate Derivatives of γ-Hydroxy-α,β-unsaturated Sulfones

  摘要：

  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.

  DOI：

  10.1021/jo981391r

文献信息

• 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.
• 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