(R)-1-phenyl-2,5-pentanediol | 437606-64-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-1-phenyl-2,5-pentanediol
• 英文别名: (4R)-5-phenylpentane-1,4-diol
• CAS: 437606-64-9
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: SVZPBLXSRVVZCW-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-phenyl-2,5-pentanediol 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (1S,2S)-1-methyl-2-benzylphospholaneborane
  参考文献：
  名称：

  Synthesis of Both Enantiomers of a P-Chirogenic 1,2-Bisphospholanoethane Ligand via Convergent Routes and Application to Rhodium-Catalyzed Asymmetric Hydrogenation of CI-1008 (Pregabalin)

  摘要：

  Both enantiomers of a P-chirogenic 1,2-bisphospholanoethane ligand are synthesized via two convergent methods. The first method relies on the chiral alkylation of 1 -((-)-menthoxy)phospholaneborane using a s-BuLi/(-)-sparteine derived chiral base. Only one enantiomer of the catalyst could be synthesized via this method because only one antipode of sparteine is available in nature. The second route relies on the combination of methylphosphine borane and a chiral 1,4-diol. Either enantiomer of the ligand can be synthesized via the second route from the appropriate enantiomer of the 1,4-diol. Asymmetric hydrogenation using catalyst precursor 36 on acetamidoacrylic acid derivatives provided modest to good enantioselectivity (77-95% ee) under low H-2 pressure (30 psi). Asymmetric hydrogenation of Cl-1008 (pregabalin) precursors, 39 and 40, provided good enantioselectivities (92%) at high catalyst loading (1 mol %) and low pressure (30 psi). Enantiomeric excesses dropped sharply with catalyst loading at this pressure. Increasing the pressure of H-2 caused a significant increase in enantiomeric excess for low catalyst loading reactions. Several studies were undertaken to further investigate the enantioselectivity dependence on both pressure and catalyst loading.

  DOI：

  10.1021/ja034715o
• 作为产物：
  描述：

  (S)-(2,3-epoxypropyl)benzene 在 lithium aluminium tetrahydride 、 乙醇 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 16.08h， 生成 (R)-1-phenyl-2,5-pentanediol
  参考文献：
  名称：

  Synthesis of Both Enantiomers of a P-Chirogenic 1,2-Bisphospholanoethane Ligand via Convergent Routes and Application to Rhodium-Catalyzed Asymmetric Hydrogenation of CI-1008 (Pregabalin)

  摘要：

  Both enantiomers of a P-chirogenic 1,2-bisphospholanoethane ligand are synthesized via two convergent methods. The first method relies on the chiral alkylation of 1 -((-)-menthoxy)phospholaneborane using a s-BuLi/(-)-sparteine derived chiral base. Only one enantiomer of the catalyst could be synthesized via this method because only one antipode of sparteine is available in nature. The second route relies on the combination of methylphosphine borane and a chiral 1,4-diol. Either enantiomer of the ligand can be synthesized via the second route from the appropriate enantiomer of the 1,4-diol. Asymmetric hydrogenation using catalyst precursor 36 on acetamidoacrylic acid derivatives provided modest to good enantioselectivity (77-95% ee) under low H-2 pressure (30 psi). Asymmetric hydrogenation of Cl-1008 (pregabalin) precursors, 39 and 40, provided good enantioselectivities (92%) at high catalyst loading (1 mol %) and low pressure (30 psi). Enantiomeric excesses dropped sharply with catalyst loading at this pressure. Increasing the pressure of H-2 caused a significant increase in enantiomeric excess for low catalyst loading reactions. Several studies were undertaken to further investigate the enantioselectivity dependence on both pressure and catalyst loading.

  DOI：

  10.1021/ja034715o

文献信息

• PROCESS FOR PREPARING PAN-CDK INHIBITORS OF THE FORMULA (I), AND INTERMEDIATES IN THE PREPARATION
  申请人：Krüger Joachim

  公开号：US20130245261A1

  公开（公告）日：2013-09-19

  The invention relates to a novel process for the preparation of pan-CDK inhibitors of the formula (I), and intermediates of the preparation.

  这项发明涉及一种新型用于制备化合物(I)的泛CDK抑制剂的方法，以及制备过程中的中间体。
• Synthesis of P-chiral bisphospholane ligands and their transition metal complexes for use as asymmetric hydrogenation catalysts
  申请人：——

  公开号：US20020087017A1

  公开（公告）日：2002-07-04

  P-chiral bisphospholane ligands and methods for their preparation are described. Use of metal/P-chiral bisphospholane complexes to catalyze asymmetric transformation reactions to provide high enantiomeric excesses of formed compounds is also described.

  描述了P-手性双膦酸配体及其制备方法。还描述了利用金属/P-手性双膦酸配合物催化不对称转化反应，以提供形成化合物的高对映体选择性过量。
• [DE] VERFAHREN ZUR HERSTELLUNG VON PAN-CDK-INHIBITOREN DER FORMEL (I), SOWIE INTERMEDIATE DER HERSTELLUNG<br/>[EN] PROCESS FOR PREPARING PAN-CDK INHIBITORS OF THE FORMULA (I), AND INTERMEDIATES IN THE PREPARATION<br/>[FR] PROCÉDÉ DE PRODUCTION D'INHIBITEURS PAN-CDK DE LA FORMULE (I), ET INTERMÉDIAIRE DE LA PRODUCTION
  申请人：BAYER PHARMA AG

  公开号：WO2012038411A1

  公开（公告）日：2012-03-29

  Die Erfindung betrifft ein neues Verfahren zur Herstellung von pan-CDK-Inhibitoren der Formel (I), sowie Intermediate der Herstellung.

  这项发明涉及一种制备pan-CDK抑制剂的新方法，其化学式为(I)，以及其制备的中间体。
• P-CHIRALE BISPHOSPHOLANE LIGANDS, THEIR TRANSITION METAL COMPLEXES
  申请人：Warner-Lambert Company LLC

  公开号：EP1341799A1

  公开（公告）日：2003-09-10
• VERFAHREN ZUR HERSTELLUNG VON PAN-CDK-INHIBITOREN DER FORMEL (I), SOWIE INTERMEDIATE DER HERSTELLUNG
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP2619186A1

  公开（公告）日：2013-07-31