(3aR,4aR,7aR,7bR)-4-cyclohexylperhydrofuro[2',3':4,5]phospholo[3,2-b]furan-2,6-dione | 913549-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aR,4aR,7aR,7bR)-4-cyclohexylperhydrofuro[2',3':4,5]phospholo[3,2-b]furan-2,6-dione
• 英文别名: (1R,2R,6R,8R)-7-cyclohexyl-3,11-dioxa-7-phosphatricyclo[6.3.0.02,6]undecane-4,10-dione
• CAS: 913549-48-1
• 化学式: C₁₄H₁₉O₄P
• 分子量: 282.276
• InChiKey: QOCHOILTFYUEKP-JYILRKAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4aR,7aR,7bR)-4-cyclohexylperhydrofuro[2',3':4,5]phospholo[3,2-b]furan-2,6-dione 在 selenium 作用下， 以 氘代氯仿 为溶剂， 生成 (3aR,3bR,6aR,7aR)-7-Cyclohexyl-7-selenoxo-hexahydro-3,4-dioxa-7λ⁵-phospha-cyclopenta[a]pentalene-2,5-dione
  参考文献：
  名称：

  New chiral monodentate phospholane ligands by highly stereoselective hydrophosphination

  摘要：

  New chiral phospholanes 6 were prepared in both enantiomeric forms starting from L- and D-tartaric acid. The key step in the synthetic sequence is the double hydrophosphination of unsaturated chiral bis(lactone) 9 by NaPhPH(BH3). This method was used for the first time in the formation of chiral phospholanes. The structure of phospholane 6a was confirmed by X-ray crystallography. sigma-Donor properties of the phospholanes were estimated by measurement of (1)J((PSe)-P-31-Se-77) coupling constants in the corresponding phosphine selenides. The new phospholanes were tested as ligands in the Rh-catalyzed enantioselective hydrogenation of functionalized standard olefins (65-92% ee). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.047
• 作为产物：
  描述：

  (3aR,3bR,6aR,7aR)-7-Cyclohexyl-hexahydro-3,4-dioxa-7-phospha-cyclopenta[a]pentalene-2,5-dione; compound with borane 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到(3aR,4aR,7aR,7bR)-4-cyclohexylperhydrofuro[2',3':4,5]phospholo[3,2-b]furan-2,6-dione
  参考文献：
  名称：

  New chiral monodentate phospholane ligands by highly stereoselective hydrophosphination

  摘要：

  New chiral phospholanes 6 were prepared in both enantiomeric forms starting from L- and D-tartaric acid. The key step in the synthetic sequence is the double hydrophosphination of unsaturated chiral bis(lactone) 9 by NaPhPH(BH3). This method was used for the first time in the formation of chiral phospholanes. The structure of phospholane 6a was confirmed by X-ray crystallography. sigma-Donor properties of the phospholanes were estimated by measurement of (1)J((PSe)-P-31-Se-77) coupling constants in the corresponding phosphine selenides. The new phospholanes were tested as ligands in the Rh-catalyzed enantioselective hydrogenation of functionalized standard olefins (65-92% ee). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.047

文献信息

• New chiral monodentate phospholane ligands by highly stereoselective hydrophosphination
  作者：Vitaliy Bilenko、Anke Spannenberg、Wolfgang Baumann、Igor Komarov、Armin Börner

  DOI：10.1016/j.tetasy.2006.06.047

  日期：2006.8

  New chiral phospholanes 6 were prepared in both enantiomeric forms starting from L- and D-tartaric acid. The key step in the synthetic sequence is the double hydrophosphination of unsaturated chiral bis(lactone) 9 by NaPhPH(BH3). This method was used for the first time in the formation of chiral phospholanes. The structure of phospholane 6a was confirmed by X-ray crystallography. sigma-Donor properties of the phospholanes were estimated by measurement of (1)J((PSe)-P-31-Se-77) coupling constants in the corresponding phosphine selenides. The new phospholanes were tested as ligands in the Rh-catalyzed enantioselective hydrogenation of functionalized standard olefins (65-92% ee). (c) 2006 Elsevier Ltd. All rights reserved.