pentane-2,4-diol | 72345-23-4

• 物质功能分类: 化学试剂 - 手性化学试剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pentane-2,4-diol
• 英文别名: (S,S)-(+)-2,4-pentanediol；2(S),4(S)-dihydroxypentane；2S,4S-2,4-Pentandiol；(4S)-pentane-2,4-diol
• CAS: 72345-23-4
• 化学式: C₅H₁₂O₂
• 分子量: 104.149
• InChiKey: GTCCGKPBSJZVRZ-ROLXFIACSA-N

物化性质

• 熔点：
  45-48 °C (lit.)
• 比旋光度：
  +41.2° (c 10, CHCl3)
• 沸点：
  111-113C
• 密度：
  0.9917 (rough estimate)
• 闪点：
  215 °F
• 溶解度：
  在EtOH中几乎透明

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29053990
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

用途：具有光学活性的试剂可用于制备强效钙拮抗剂NIP-101。

反应信息

• 作为反应物：
  描述：

  原异丁酸三甲酯 、 potassium tert-butylate 、 pentane-2,4-diol 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 生成 2-isopropyl-2-methoxy-4(R),6(R)-dimethyl-1,3-dioxane
  参考文献：
  名称：

  12-hetero substituted 6,11-ethano-6,11-dihydrobenzo (b) quinolizinium

  摘要：

  1-杂代替的6,11-乙烷-6,11-二氢苯并[b]喹啉盐，含有它们的药物组合物，以及利用它们治疗或预防神经退行性疾病或神经毒性损伤的方法。

  公开号：

  US05380729A1
• 作为产物：
  描述：

  乙酰丙酮 在 <(S)-2,2'-dimethyl-6,6'-bis(diphenylphosphino)biphenyl> 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、10.0 MPa 条件下， 反应 6.0h， 以12%的产率得到pentane-2,4-diol
  参考文献：
  名称：

  Ruthenium(II) complexes with the atropisomeric diphosphine 2,2′-bis(diphenylphosphino)-6,6′-dimethylbiphenyl in the enantioselective hydrogenation of pentane-2,4-dione

  摘要：

  The five-co-ordinate complex [RuCl2(PPh3){(S)-biphemp}] [(S)-biphemp = (S)-2,2'-bis(diphenyl-phosphino)-6,6'-dimethylbiphenyl] reacts with pentane-2,4-dione (Hacac) in the presence of NEt3 to give [RuCl(acac)(PPh3){(S)-biphemp}], which has been isolated in the solid state. The reaction of the chlorohydride [RuHCl(PPh3){(S)-biphemp}[ with Hacac gives [RuH(acac)(PPh3){(S)-biplhemp}] and eventually [Ru(acac)2{(S)-biphemp}], which were identified spectroscopically. The relevance of the formation of these new species to the enantioselective hydrogenation of 2,4-diketones to the corresponding diols has been studied by testing [RuCl2(PPh3){(S)-biphemp}] and some of its derivatives as catalyst precursors, also in connection with the use of modifiers such as anhydrous HCl, PPh3, chloride ions, NEt3 and HBF4. The hydrogenation reaction has also been followed under ambient conditions by means of P-31 and H-1 NMR spectroscopy. The activity and selectivity data confirm that for optimum efficiency two chloride ligands must be present in the catalyst precursor. These data are discussed in view of the assessment of a possible reaction pathway for the catalytic reaction.

  DOI：

  10.1039/dt9950000049

文献信息

• 12-hetero substituted 6,11-ethano-6,11-dihydrobenzo (b) quinolizinium
  申请人：Sterling Winthrop Inc.

  公开号：US05380729A1

  公开（公告）日：1995-01-10

  1-Hetero substituted 6,11-ethano-6,11-dihydrobenzo[b]quinolizinium salts, pharmaceutical compositions containing them, and methods for the treatment or prevention of neurodegenerative disorders or neurotoxic injuries utilizing them.

  1-杂代替的6,11-乙烷-6,11-二氢苯并[b]喹啉盐，含有它们的药物组合物，以及利用它们治疗或预防神经退行性疾病或神经毒性损伤的方法。
• Ruthenium(<scp>II</scp>) complexes with the atropisomeric diphosphine 2,2′-bis(diphenylphosphino)-6,6′-dimethylbiphenyl in the enantioselective hydrogenation of pentane-2,4-dione
  作者：Antonio Mezzetti、Andreas Tschumper、Giambattista Consiglio

  DOI：10.1039/dt9950000049

  日期：——

  The five-co-ordinate complex [RuCl2(PPh3)(S)-biphemp}] [(S)-biphemp = (S)-2,2'-bis(diphenyl-phosphino)-6,6'-dimethylbiphenyl] reacts with pentane-2,4-dione (Hacac) in the presence of NEt3 to give [RuCl(acac)(PPh3)(S)-biphemp}], which has been isolated in the solid state. The reaction of the chlorohydride [RuHCl(PPh3)(S)-biphemp}[ with Hacac gives [RuH(acac)(PPh3)(S)-biplhemp}] and eventually [Ru(acac)2(S)-biphemp}], which were identified spectroscopically. The relevance of the formation of these new species to the enantioselective hydrogenation of 2,4-diketones to the corresponding diols has been studied by testing [RuCl2(PPh3)(S)-biphemp}] and some of its derivatives as catalyst precursors, also in connection with the use of modifiers such as anhydrous HCl, PPh3, chloride ions, NEt3 and HBF4. The hydrogenation reaction has also been followed under ambient conditions by means of P-31 and H-1 NMR spectroscopy. The activity and selectivity data confirm that for optimum efficiency two chloride ligands must be present in the catalyst precursor. These data are discussed in view of the assessment of a possible reaction pathway for the catalytic reaction.