(R)-4-Hydroxybutyl methyl sulfoxide | 155184-99-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (R)-4-Hydroxybutyl methyl sulfoxide
• 英文别名: 4-[(R)-methylsulfinyl]butan-1-ol
• CAS: 155184-99-9
• 化学式: C₅H₁₂O₂S
• 分子量: 136.215
• InChiKey: NACRUHSUUTYRMW-MRVPVSSYSA-N

物化性质

• 沸点：
  321.7±25.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-Hydroxybutyl methyl sulfoxide 在 sodium azide 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (S)-Sulforaphane
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

  摘要：

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

  DOI：

  10.1021/jo00082a016
• 作为产物：
  描述：

  (R)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以92%的产率得到(R)-4-Hydroxybutyl methyl sulfoxide
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

  摘要：

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

  DOI：

  10.1021/jo00082a016

文献信息

• HPLC enantioseparation on a homochiral MOF–silica composite as a novel chiral stationary phase
  作者：Koichi Tanaka、Toshihide Muraoka、Yasuhiro Otubo、Hiroki Takahashi、Atsushi Ohnishi

  DOI：10.1039/c5ra26520g

  日期：——

  frontier in the development of chiral stationary phases for chromatographic enantioseparation involves homochiral metal–organic frameworks (MOFs). Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for high-performance liquid chromatography to separate the enantiomers

  色谱对映体分离的手性固定相开发的最后一个领域涉及同手性金属-有机骨架（MOF）。以对映体（R）-2,2'-二羟基-1,1'-双萘-6,6'-二羧酸为起始原料，制备了三种均手性MOF，进一步用作高性能液体的手性固定相色谱分离各种消旋亚砜，仲醇，β-内酰胺，安息香，黄烷酮和环氧化物的对映异构体。实验结果表明，对映体分离具有出色的性能，并强调了在手性MOF色谱柱上进行对映体分离是可行的。