(R)-1-(phenylsulfonyl)heptan-2-ol | 224634-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-(phenylsulfonyl)heptan-2-ol
• 英文别名: (2R)-1-(benzenesulfonyl)heptan-2-ol
• CAS: 224634-47-3
• 化学式: C₁₃H₂₀O₃S
• 分子量: 256.366
• InChiKey: NVNORMOEJVRONY-GFCCVEGCSA-N

物化性质

• 沸点：
  427.3±37.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(phenylsulfonyl)heptan-2-ol 在 正丁基锂 、 对甲苯磺酸 、 三乙胺 作用下， 以 苯 为溶剂， 反应 32.0h， 生成 (-)-(R)-5-pentyl-2(5H)-furanone
  参考文献：
  名称：

  Enantioselective hydrogenation of β-keto sulfones with chiral Ru(II)-catalysts: synthesis of enantiomerically pure butenolides and γ-butyrolactones

  摘要：

  A series of beta-hydroxy sulfones were synthesized with high enantioselectivities via a new enantioselective ruthenium-catalyzed hydrogenation using MeO-BIPHEP as a ligand. Some beta-hydroxy sulfones were used in the synthesis of optically active butenolides and gamma-butyrolactones with high yields and enantioselectivities over 95%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00113-5
• 作为产物：
  描述：

  己酰氯 在 正丁基锂 、 CODRu(2-methylallyl)2 、 氢溴酸 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲醇 、 丙酮 为溶剂， -30.0~65.0 ℃ 、100.0 kPa 条件下， 反应 24.5h， 生成 (R)-1-(phenylsulfonyl)heptan-2-ol
  参考文献：
  名称：

  Enantioselective hydrogenation of β-keto sulfones with chiral Ru(II)-catalysts: synthesis of enantiomerically pure butenolides and γ-butyrolactones

  摘要：

  A series of beta-hydroxy sulfones were synthesized with high enantioselectivities via a new enantioselective ruthenium-catalyzed hydrogenation using MeO-BIPHEP as a ligand. Some beta-hydroxy sulfones were used in the synthesis of optically active butenolides and gamma-butyrolactones with high yields and enantioselectivities over 95%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00113-5

文献信息

• General synthesis of chiral β-hydroxy sulfones via enantioselective ruthenium-catalyzed hydrogenation
  作者：P Bertus、P Phansavath、V Ratovelomanana-Vidal、J.-P Genêt、A.R Touati、T Homri、B.Ben Hassine

  DOI：10.1016/s0040-4039(99)00453-0

  日期：1999.4

  A new ruthenium-promoted hydrogenation of β-keto sulfones using MeO-BIPHEP as ligand is reported with complete conversions and enantiomeric excesses over 95%.

  据报道，使用MeO-BIPHEP作为配体，钌促进了β-酮砜的氢化反应，完全转化，对映体过量超过95％。
• Enantioselective bioreduction of β-keto sulfones with the fungus Curvularia lunata
  作者：Vicente Gotor、Francisca Rebolledo、Ramón Liz

  DOI：10.1016/s0957-4166(01)00048-9

  日期：2001.3

  beta -Keto sulfones bearing bulky groups are reduced with high enantioselectivities to the corresponding optically active beta -hydroxy sulfones by the fungus Curvularia lunata CECT 2130; the cells can be re-used without loss of their catalytic activity. (C) 2001 Published by Elsevier Science Ltd.
• Enantioselective hydrogenation of β-keto sulfones with chiral Ru(II)-catalysts: synthesis of enantiomerically pure butenolides and γ-butyrolactones
  作者：P Bertus、P Phansavath、V Ratovelomanana-Vidal、J.-P Genêt、A.R Touati、T Homri、B.Ben Hassine

  DOI：10.1016/s0957-4166(99)00113-5

  日期：1999.4

  A series of beta-hydroxy sulfones were synthesized with high enantioselectivities via a new enantioselective ruthenium-catalyzed hydrogenation using MeO-BIPHEP as a ligand. Some beta-hydroxy sulfones were used in the synthesis of optically active butenolides and gamma-butyrolactones with high yields and enantioselectivities over 95%. (C) 1999 Elsevier Science Ltd. All rights reserved.