2,5-dimethyl-3,4-bis(ethoxyphosphoryl)thiophene | 860815-28-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2,5-dimethyl-3,4-bis(ethoxyphosphoryl)thiophene
• 英文别名: 2,5-dimethyl-3,4-bis(diethoxyphosphoryl)-thiophene；3,4-Bis(diethoxyphosphoryl)-2,5-dimethylthiophene
• CAS: 860815-28-7
• 化学式: C₁₄H₂₆O₆P₂S
• 分子量: 384.37
• InChiKey: JNJCSKJHFKEERS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  99.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-3,4-bis(ethoxyphosphoryl)thiophene 在 lithium aluminium tetrahydride 、 正丁基锂 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 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 、 亚磷酸三乙酯 在 palladium diacetate 作用下， 反应 3.0h， 以48%的产率得到2,5-dimethyl-3,4-bis(ethoxyphosphoryl)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

• Metallic catalysts for chemo-, regio-and stereoselective reactions, and corresponding precursors
  申请人：Sannicolo Francesco

  公开号：US20050107248A1

  公开（公告）日：2005-05-19

  Metallic catalysts of the general formula (I) and their precursors, suitable for chemo- regio- and stereoselective reactions, derived from ortho-bis-(1-phospholanyl)-heteroarenes. The new catalysts are characterized by the presence of two homomorphic phospholanic rings set in adjacent positions of an aromatic pentatomic heterocycle.

  具有一般公式(I)的金属催化剂及其前体，适用于化学-区域-和对映选择性反应，源自邻双(1-磷杂环戊烷基)-杂芳烃。这些新催化剂的特点是存在两个同态的磷杂环戊烷环，它们设置在芳香五原子杂环的相邻位置。
• Thiophene compound having phosphoric ester and process for producing the same
  申请人：Kakiuchi Nobuyuki

  公开号：US20100019229A1

  公开（公告）日：2010-01-28

  A thiophene compound having a phosphate group, for example, one represented by the formula [1]. The compound has high resistance to heat and oxidation and can be improved in solubility or dispersibility in various solvents. (In the formula, R 1 and R 2 each independently represents, e.g., hydrogen, halogeno, cyano, or phenyl optionally substituted by W; and R 3 to R 6 each independently represents —OR 7 , SR 8 , or —NR 9 2 , provided that R 7 to R 9 each independently represents hydrogen, C 1-10 alkyl, or phenyl optionally substituted by W and W represents halogeno, cyano, nitro, hydroxyl, mercapto, amino, formyl, carboxy, C 1-10 alkyl, etc.)

  一种含磷酸基的噻吩化合物，例如，由公式[1]表示的化合物。该化合物具有高耐热性和抗氧化性，并且可以在各种溶剂中改善溶解性或分散性。（在公式中，R1和R2各自独立地表示氢，卤素，氰基或苯基，可选择地被W取代；而R3到R6各自独立地表示-OR7，SR8或-NR92，前提是R7到R9各自独立地表示氢，C1-10烷基或可选择地被W取代的苯基，W表示卤素，氰基，硝基，羟基，巯基，氨基，甲酰基，羧基，C1-10烷基等。）
• METALORGANIC CATALYSTS FOR CHEMO-, REGIO- AND STEREOSELECTIVE REACTIONS, AND CORRESPONDING PRECURSORS
  申请人：CHEMI S.p.A.

  公开号：EP1490173A2

  公开（公告）日：2004-12-29
• US7307037B2
  申请人：——

  公开号：US7307037B2

  公开（公告）日：2007-12-11
• US8030438B2
  申请人：——

  公开号：US8030438B2

  公开（公告）日：2011-10-04