2,5-dimethyl-3,4-bis(phosphino)thiophene | 596127-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,5-dimethyl-3,4-bis(phosphino)thiophene
• 英文别名: 2,5-dimethyl-3,4-bis(diphosphino)-thiophene；(2,5-Dimethyl-4-phosphanylthiophen-3-yl)phosphane
• CAS: 596127-56-9
• 化学式: C₆H₁₀P₂S
• 分子量: 176.159
• InChiKey: CUDJEVNEMDLFSB-UHFFFAOYSA-N

物化性质

• 沸点：
  309.6±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-3,4-bis(phosphino)thiophene 、 (4S,7S)-4,7-dimethyl-1,3,2-dioxathiepane 2,2-dioxide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 以70%的产率得到3,5-dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene
  参考文献：
  名称：

  2,5-Dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene:  First Member of the Hetero-DuPHOS Family

  摘要：

  The 2,5-dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholanolthiophene (UluPHOS), a new thiophene-based analogue of (RR)-1,2-bis(phospholano)benzene (Me-DuPHOS), was synthesized, geometrically and electronically characterized, and employed as ligand of Rh and Ru in some standard hydrogenation reactions of prostereogenic functionalized carbon-carbon and carbon-oxygen double bonds. The synthesis of UlluPHOS is much easier than that provided for Me-DuPHOS. UlluPHOS and Me-DuPHOS display very similar geometries, while the electronic availability of the former is higher than that exhibited by the latter. The Rh and Ru complexes of UIluPHOS produced excellent enantiomeric excesses (98.9-99.5%) in the hydrogenation of N-acetyl-alpha-enamino acids and reaction rates higher than those found when employing the analogous complexes of Me-DuPHOS.

  DOI：

  10.1021/jo050390d
• 作为产物：
  描述：

  2,5-dimethyl-3,4-diiodo-thiophene 在 palladium diacetate lithium aluminium tetrahydride 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2,5-dimethyl-3,4-bis(phosphino)thiophene
  参考文献：
  名称：

  2,5-Dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene:  First Member of the Hetero-DuPHOS Family

  摘要：

  The 2,5-dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholanolthiophene (UluPHOS), a new thiophene-based analogue of (RR)-1,2-bis(phospholano)benzene (Me-DuPHOS), was synthesized, geometrically and electronically characterized, and employed as ligand of Rh and Ru in some standard hydrogenation reactions of prostereogenic functionalized carbon-carbon and carbon-oxygen double bonds. The synthesis of UlluPHOS is much easier than that provided for Me-DuPHOS. UlluPHOS and Me-DuPHOS display very similar geometries, while the electronic availability of the former is higher than that exhibited by the latter. The Rh and Ru complexes of UIluPHOS produced excellent enantiomeric excesses (98.9-99.5%) in the hydrogenation of N-acetyl-alpha-enamino acids and reaction rates higher than those found when employing the analogous complexes of Me-DuPHOS.

  DOI：

  10.1021/jo050390d

文献信息

• 2,5-Dimethyl-3,4-bis[(2<i>R</i>,5<i>R</i>)-2,5-dimethylphospholano]thiophene:  First Member of the Hetero-DuPHOS Family
  作者：Tiziana Benincori、Tullio Pilati、Simona Rizzo、Franco Sannicolò、Mark J. Burk、Lorenzo de Ferra、Elio Ullucci、Oreste Piccolo

  DOI：10.1021/jo050390d

  日期：2005.7.1

  The 2,5-dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholanolthiophene (UluPHOS), a new thiophene-based analogue of (RR)-1,2-bis(phospholano)benzene (Me-DuPHOS), was synthesized, geometrically and electronically characterized, and employed as ligand of Rh and Ru in some standard hydrogenation reactions of prostereogenic functionalized carbon-carbon and carbon-oxygen double bonds. The synthesis of UlluPHOS is much easier than that provided for Me-DuPHOS. UlluPHOS and Me-DuPHOS display very similar geometries, while the electronic availability of the former is higher than that exhibited by the latter. The Rh and Ru complexes of UIluPHOS produced excellent enantiomeric excesses (98.9-99.5%) in the hydrogenation of N-acetyl-alpha-enamino acids and reaction rates higher than those found when employing the analogous complexes of Me-DuPHOS.