(S)-1-phenyl-2,5-pentanediol | 757954-64-6

• 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: (S)-1-phenyl-2,5-pentanediol
• 英文别名: (S)-5-phenyl-pentane-1,4-diol；(4S)-5-phenylpentane-1,4-diol
• CAS: 757954-64-6
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: SVZPBLXSRVVZCW-NSHDSACASA-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：

  (S)-1-phenyl-2,5-pentanediol 在 氯化亚砜 、 ruthenium trichloride 、 sodium periodate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 20.0h， 以67%的产率得到(4S)-4-benzyl-1,3,2-dioxathiepane-2,2-dioxide
  参考文献：
  名称：

  立体选择性环化和锥体反转策略的 P-Chirogenic Phospholane 合成

  摘要：

  报道了 P-chirogenic 单和双磷烷的制备。所证明的方法采用环状硫酸盐与初级膦在碱存在下的立体选择性环化，以生成“顺式”或“顺式/顺式”P-手性磷杂环戊烷，然后通过热诱导锥体反转提供“反式”或“反式/反式” “ P-chirogenic 磷烷。将一种“反式/反式”磷烷的铑络合物应用于底物前体对药物候选普瑞巴林的高度对映选择性不对称氢化。

  DOI：

  10.1021/ja048079l
• 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 (S)-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

• Preparation of P-chirogenic phospholanes and their use in asymmetric synthesis
  申请人：Hoge Stewart Garrett

  公开号：US20050222464A1

  公开（公告）日：2005-10-06

  Materials and methods for preparing P-chirogenic monophospholanes and bisphospholanes are disclosed. The methods employ stereoselective cyclization to generate the phospholane rings followed by pyramidal inversion to access a variety of P-chirogenic phospholanes. When bound to transition metals such as rhodium, the disclosed P-chirogenic phospholanes may be used as catalysts in asymmetric synthesis of valuable pharmaceutical chemical entities, including pregabalin.

  本文披露了制备P-手性单膦杂环和双膦杂环的材料和方法。该方法采用立体选择性环化来生成膦杂环，然后通过金字塔翻转来访问各种P-手性膦杂环。当与铑等过渡金属结合时，所披露的P-手性膦杂环可用作催化剂，在制备有价值的药物化学物质，包括pregabalin的不对称合成中使用。
• PREPARATION OF P-CHIROGENIC PHOSPHOLANES AND THEIR USE IN ASYMETRIC SYNTHESIS
  申请人：Warner-Lambert Company LLC

  公开号：EP1735324A1

  公开（公告）日：2006-12-27
• US7390931B2
  申请人：——

  公开号：US7390931B2

  公开（公告）日：2008-06-24
• [EN] PREPARATION OF P-CHIROGENIC PHOSPHOLANES AND THEIR USE IN ASYMETRIC SYNTHESIS<br/>[FR] PREPARATION DE PHOSPHOLANES P-CHIROGENES ET UTILISATION DE CEUX-CI DANS UNE SYNTHESE ASYMETRIQUE
  申请人：WARNER LAMBERT CO

  公开号：WO2005095424A1

  公开（公告）日：2005-10-13

  Materials and methods for preparing P-chirogenic monophospholanes and bisphospholanes are disclosed. The methods employ stereoselective cyclization to generate the phospholane rings followed by pyramidal inversion to access a variety of P-chirogenic phospholanes. When bound to transition metals such as rhodium, the disclosed P-chirogenic phospholanes may be used as catalysts in asymmetric synthesis of valuable pharmaceutical chemical entities, including pregabalin.
• 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)
  作者：Garrett Hoge

  DOI：10.1021/ja034715o

  日期：2003.8.1

  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.