(S)-(+)-3-methyl-1-phenylsulfonyl-2-butanol | 296758-99-1

• 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: (S)-(+)-3-methyl-1-phenylsulfonyl-2-butanol
• 英文别名: (S)-3-methyl-1-(phenylsulfonyl)butan-2-ol；(2S)-1-(benzenesulfonyl)-3-methylbutan-2-ol
• CAS: 296758-99-1
• 化学式: C₁₁H₁₆O₃S
• 分子量: 228.312
• InChiKey: NXOQSXUVDDGMKZ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (S)-(+)-3-methyl-1-phenylsulfonyl-2-butanol 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 (3S)-2-methyl-4-phenylsulfonyl-6-heptanol
  参考文献：
  名称：

  Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

  摘要：

  Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone I were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S, 5S)-2,6-dimethyl3, 5-heptanediol 12a. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.013
• 作为产物：
  描述：

  3-methyl-1-phenylsulfonyl-2-butanone 在 phosphate buffer 、 葡萄糖 、 Pichia minuta IAM 12215 strain 作用下， 反应 27.5h， 以92%的产率得到(S)-(+)-3-methyl-1-phenylsulfonyl-2-butanol
  参考文献：
  名称：

  Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

  摘要：

  Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone I were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S, 5S)-2,6-dimethyl3, 5-heptanediol 12a. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.013

文献信息

• Catalytic asymmetric conjugate boration of α,β-unsaturated sulfones
  作者：Abraham L. Moure、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1039/c1cc11949d

  日期：——

  The alpha,beta-unsaturated sulfones are suitable activated olefins in catalytic asymmetric conjugate beta-boration. These substrates undergo smooth conjugate addition of bis(pinacolato)diboron [B(2)(pin)(2)] catalyzed by nonracemic Cu(I)-diphosphine complexes to provide, upon subsequent oxidation, beta-hydroxy sulfones in good yields and high enantiocontrol.

  α，β-不饱和砜是催化不对称共轭β-硼酸酯化反应中合适的活化烯烃。这些底物通过非外消旋的Cu（I）-二膦配合物催化双（pinacolato）diboron [B（2）（pin）（2）]的平滑共轭加成，从而在随后的氧化反应中，以高收率和高收率提供β-羟基砜对映体控制。
• Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones
  作者：Chihiro Hiraoka、Masaaki Matsuda、Yuya Suzuki、Shigeo Fujieda、Mina Tomita、Ken-ichi Fuhshuku、Rika Obata、Shigeru Nishiyama、Takeshi Sugai

  DOI：10.1016/j.tetasy.2006.12.013

  日期：2006.12

  Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone I were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S, 5S)-2,6-dimethyl3, 5-heptanediol 12a. (c) 2007 Elsevier Ltd. All rights reserved.