erythro-2-(2,4-difluorophenyl)-2-<1-(methylthio)ethyl>oxirane

• 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: erythro-2-(2,4-difluorophenyl)-2-<1-(methylthio)ethyl>oxirane
• 英文别名: (2R)-2-(2,4-difluorophenyl)-2-[(1S)-1-methylsulfanylethyl]oxirane
• 化学式: C₁₁H₁₂F₂OS
• 分子量: 230.278
• InChiKey: GIZLWCWHONDDTF-WRWORJQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 erythro-2-(2,4-difluorophenyl)-2-<1-(methylthio)ethyl>oxirane 在 potassium carbonate 作用下， 生成 erythro-2-(2,4-difluorophenyl)-2-methylthio-1,3-butanediol
  参考文献：
  名称：

  Stereospecific Acetolysis ofthreo- anderythro-2-Aryl-2-[1-(methylthio)ethyl]oxiranes

  摘要：

  Threo-2-aryl-2-[1-(methylthio)ethyl]oxiranes (1a—d) were reacted with acetic acid to give two types of unexpected ring-opening products, threo-1-acetoxy-2-aryl-3-methylthio-2-butanols (4a—d) and mono-O-acetyl derivatives of threo-2-aryl-2-methylthio-1,3-butanediol (5a—d and 6a—d). On the other hand, erythro-2-aryl-2-[1-(methylthio)ethyl]oxiranes (2a—d) gave erythro-1-acetoxy-2-aryl-3-methylthio-2-butanols (7a—d) and mono-O-acetyl derivatives of erythro-2-aryl-2-methylthio-1,3-butanediol (8a—d and 9a—d). It is suggested that these products are generated from thiiranium ionic intermediates, because they all completely retain the relative configuration of the starting oxiranes.

  DOI：

  10.1246/bcsj.68.1731
• 作为产物：
  描述：

  1,3-二氟苯 在 三氯化铝 、 sodium hydride 、 二甲基亚砜 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 13.08h， 生成 erythro-2-(2,4-difluorophenyl)-2-<1-(methylthio)ethyl>oxirane
  参考文献：
  名称：

  立体选择性合成抗真菌剂 threo-2-(2,4-Difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol (SM-8668)

  摘要：

  描述了抗真菌剂threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol (SM-8668)的立体选择性合成. 关键步骤是中间体苏-2(2,4-二氟苯基)-2-(1-取代乙基)环氧乙烷的选择性合成。苏式-2-(2,4-二氟苯基)-2-(1-甲硫基乙基)环氧乙烷通过1-(2,4-二氟苯基)-2-甲硫基-1-丙酮与二甲基氧锍甲基化物反应苏式选择性合成由疏水溶剂和碱性水溶液组成的异质介质。

  DOI：

  10.1246/bcsj.67.1427

文献信息

• Optical Resolution of<i>dl</i>-<i>threo</i>-2-(2,4-Difluorophenyl)-2-[1-(methylthio)ethyl]oxirane: Its Application to the Synthesis of SM-9164, a Biologically Active Enantiomer of Antifungal Agent SM-8668
  作者：Hiroshi Miyauchi、Naohito Ohashi

  DOI：10.1246/bcsj.68.3591

  日期：1995.12

  carboxylic acid, followed by separation of the resultant diastereomers, hydrolysis of the ester, and dehydration of the 1,2-diol to the oxirane. This new optical resolution method was applied to the synthesis of SM-9164, a biologically active enantiomer of antifungal agent SM-8668. Thus, the optically active isomer of SM-8668 was prepared efficiently in eight steps from m-difluorobenzene.

  苏-2-(2,4-二氟苯基)-2-[1-(甲硫基)乙基]环氧乙烷的外消旋体通过与手性羧酸反应分离成两个对映体，然后分离得到的非对映体，水解酯，并将 1,2-二醇脱水成环氧乙烷。这种新的光学拆分方法被应用于抗真菌剂 SM-8668 的生物活性对映体 SM-9164 的合成。因此，SM-8668 的旋光异构体可以通过八步从间二氟苯有效地制备。
• Stereoselective Synthesis of Antifungal Agent<i>threo</i>-2-(2,4-Difluorophenyl)-3-methylsulfonyl-1-(1<i>H</i>-1,2,4-triazol-1-yl)-2-butanol (SM-8668)
  作者：Ikutaro Saji、Katsumi Tamoto、Yoshihiro Tanaka、Hiroshi Miyauchi、Koji Fujimoto、Naohito Ohashi

  DOI：10.1246/bcsj.67.1427

  日期：1994.5

  4-triazol-1-yl)-2-butanol (SM-8668) is described. The key step is the selective synthesis of intermediate threo-2(2,4-difluorophenyl)-2-(1-substituted ethyl)oxirane. threo-2-(2,4-Difluorophenyl)-2-(1-methylthioethyl)oxirane was synthesized threo-selectively by the reaction of 1-(2,4-difluorophenyl)-2-methylthio-1-propanone with dimethyloxosulfonium methylide in a heterogeneous media consisting of a hydrophobic solvent

  描述了抗真菌剂threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol (SM-8668)的立体选择性合成. 关键步骤是中间体苏-2(2,4-二氟苯基)-2-(1-取代乙基)环氧乙烷的选择性合成。苏式-2-(2,4-二氟苯基)-2-(1-甲硫基乙基)环氧乙烷通过1-(2,4-二氟苯基)-2-甲硫基-1-丙酮与二甲基氧锍甲基化物反应苏式选择性合成由疏水溶剂和碱性水溶液组成的异质介质。
• Kawanishi, Hiroyuki; Morimoto, Hiroshi; Nakano, Takao, Heterocycles, 1998, vol. 49, # 1, p. 181 - 189
  作者：Kawanishi, Hiroyuki、Morimoto, Hiroshi、Nakano, Takao、Watanabe, Tatsuya、Oda, Kuniyuki、Tsujihara, Kenji

  DOI：——

  日期：——
• Stereospecific Acetolysis of<i>threo</i>- and<i>erythro</i>-2-Aryl-2-[1-(methylthio)ethyl]oxiranes
  作者：Hiroshi Miyauchi、Toshio Nakamura、Naohito Ohashi

  DOI：10.1246/bcsj.68.1731

  日期：1995.6

  Threo-2-aryl-2-[1-(methylthio)ethyl]oxiranes (1a—d) were reacted with acetic acid to give two types of unexpected ring-opening products, threo-1-acetoxy-2-aryl-3-methylthio-2-butanols (4a—d) and mono-O-acetyl derivatives of threo-2-aryl-2-methylthio-1,3-butanediol (5a—d and 6a—d). On the other hand, erythro-2-aryl-2-[1-(methylthio)ethyl]oxiranes (2a—d) gave erythro-1-acetoxy-2-aryl-3-methylthio-2-butanols (7a—d) and mono-O-acetyl derivatives of erythro-2-aryl-2-methylthio-1,3-butanediol (8a—d and 9a—d). It is suggested that these products are generated from thiiranium ionic intermediates, because they all completely retain the relative configuration of the starting oxiranes.