2-(p-toluenesulfonylmethyl)oxirane | 118356-16-4

• 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: 2-(p-toluenesulfonylmethyl)oxirane
• 英文别名: (tosylmethyl)oxirane；2-[(4-Methylphenyl)sulfonylmethyl]oxirane
• CAS: 118356-16-4
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: MGIOQFMNHZDMOD-UHFFFAOYSA-N

物化性质

• 熔点：
  50-51 °C(Solv: toluene (108-88-3))
• 沸点：
  391.4±34.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-toluenesulfonylmethyl)oxirane 在 水 、 甲基锂 、 lithium bromide 作用下， 以89%的产率得到(E)-3-(p-toluenesulfonyl)-2-propene-1-ol
  参考文献：
  名称：

  Substituted lithium (E)-3-lithio-3-tosyl-2-propenolates: useful intermediates in organic synthesis

  摘要：

  DOI：

  10.1021/jo00268a004
• 作为产物：
  描述：

  p-tolylsulfanylmethyl-oxirane 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 以84%的产率得到2-(p-toluenesulfonylmethyl)oxirane
  参考文献：
  名称：

  从环氧乙烷简单合成 β-乙酰氧基硫氰酸酯

  摘要：

  摘要描述了一种方便且简单的方法，该方法通过相应的环氧乙烷与硫氰酸根阴离子的区域选择性开环然后乙酰化来制备以前未知的 β-乙酰氧基硫氰酸盐。该方法的优点是反应时间更短、产物产率更高且易于处理。

  DOI：

  10.1080/00397911.2010.494817

文献信息

• Synthesis of β- and γ-hydroxy sulfones by regioselective opening of β,γ-epoxy sulfones
  作者：Carmen Nájera、José Miguel Sansano

  DOI：10.1016/s0040-4020(01)90534-4

  日期：1990.1

  sulfones react regio-selectively with organomagnesium compounds in the presence or not of catalytic amounts of copper(I) bromide to afford β-hydroxy sulfones 2 or γ-tosylated allylic alcoholates 5 respectively. The Michael type addition of Grignard reagents to intermediates 5 in the presence of catalytic amount of copper(l) bromide yields γ-hydroxy sulfones 6. The PCC oxidation of β- and γ-hydroxy sulfones

  衍生自烯丙基砜的β，γ-环氧砜1在有或没有催化量的溴化铜（I）存在下与有机镁化合物区域选择性反应，分别得到β-羟基砜2或γ-甲苯磺酸化的烯丙基醇化物5。在催化量的溴化铜（l）存在下，将格氏试剂的迈克尔类型加到中间体5会生成γ-羟基砜6。β-和γ-羟基砜的PCC氧化分别得到β-和γ-氧代砜10和11。对于γ-OXO砜，用DBU处理 得到α-取代的α，β-不饱和羰基化合物。
• Optically active isocarbostyril derivatives and a method of preparing the same
  申请人：NISSHIN FLOUR MILLING CO., LTD.

  公开号：EP0165110A1

  公开（公告）日：1985-12-18

  Four different optical isomers of a new compound, 1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"- isocarbostyriloxy)-2-propanol are now provided as new substances. These four optical isomers are now nominated as (2R, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy)-2-propanol, (2S, 1'S)-1-[2'-(o-meth- oxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy)-2-propanol, (2S, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methyl- ethylaminol-3-(4"-isocarbostyriloxy)-2-propanol, and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"- isocarbostyriloxy)-2-propanol, respectively. There four optical isomers have different activities for their β-adrenergic-blocking effect and α-adrenergic-blocking effect and are expectable to be more valuable agent for therapeutic treatment of various cardiovascular diseases, as compared to an optically inactive racemic mixture of said isomer compounds. These four optical isomers may be produced and isolated from each other by chromatographing (1'S)- or (1'R-N-[2'-(o-methoxyphenoxy)-1'-methylethyl]-5-(d'-iso- carbostyriloxymethyl)-2-oxalidones to isolate either its (5R; 1'S)-isomer and its (5S, 1'S)-isomer, or its (55, 1'R)-isomer and its (5R, 1'R)-isomer therefrom separately, and then hydrolysing each of these isolated isomers under alkaline conditions to obtain separately (2R,1'S)-, (2S, 1'S)-, (2S, 1'R)-and (2R, 1'R)-1-(2'-(methoxyphenoxy)-1'-methylethylamino) -3-(4"-isocarbostyriloxy)-2-propanols.

  一种新化合物--1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羧基吡咯烷酮氧基)-2-丙醇的四种不同光学异构体现作为新物质提供。这四种光学异构体现命名为 (2R，1'S)-1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羰基吡咯烷酮氧基)-2-丙醇、(2S，1'S)-1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羰基吡咯烷酮氧基)-2-丙醇、(2S，1'R)-1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羧基吡咯烷酮氧基)-2-丙醇，以及(2R，1'R)-1-[2'-(邻甲氧基苯氧基)-1'-甲基乙基氨基]-3-(4"-异羧基吡咯烷酮氧基)-2-丙醇。这四种光学异构体的β-肾上腺素能阻断作用和α-肾上腺素能阻断作用具有不同的活性，与上述异构体化合物的光学非活性外消旋混合物相比，有望成为治疗各种心血管疾病的更有价值的药物。这四种光学异构体可通过色谱法制备并相互分离出(1'S)-或(1'R-N-[2'-(邻甲氧基苯氧基)-1'-甲基乙基]-5-(d'-异羧基吡咯氧甲基)-2-恶唑烷酮，从而分离出其(5R；1'S)-异构体和它的(5S, 1'S)-异构体，或它的(55, 1'R)-异构体和它的(5R, 1'R)-异构体，然后在碱性条件下水解这些分离出的异构体，分别得到(2R、1'S)-、(2S，1'S)-、(2S，1'R)-和(2R，1'R)-1-(2'-(甲氧基苯氧基)-1'-甲基乙基氨基)-3-(4"-异碳酸基吡咯烷酮氧基)-2-丙醇。
• β,γ-efoxy sulfones in organic synthesis. Part 2: Preparation of β,γ-bifunctionalized sulfones
  作者：Carmen Nájera、José M. Sansano

  DOI：10.1016/s0040-4020(01)87131-3

  日期：1991.1

  Heteronucleophiles reagents react with beta,gamma-epoxy sulfones 1 at the gamma-position in the presence of Ti(OPr(i))4 or magnesium halides to afford regioselectively gamma-functionalized beta-hydroxy sulfones 2. With soft nucleofiles such as sodium azide, triphenylphosphine, or sodium benzethiolate the reaction takes place in the absence of Lewis acids. In the case of basic reagents such as sodium methoxide or diethylamine the corresponding regioisomers, the beta-functionalized gamma-hydroxy sulfones 3 were exclusively obtained. The preparation of compounds 3 (R2 = H) was also carried out starting from 3-tosyl-2-propen-1-ol (4) by Micheal addition of different heteronucleophiles.
• NAJERA, CARMEN;YUS, MIGUEL, J. ORG. CHEM., 54,(1989) N, C. 1491-1499
  作者：NAJERA, CARMEN、YUS, MIGUEL

  DOI：——

  日期：——
• NAJERA, CARMEN;SANSANO, JOSE MIGUEL, TETRAHEDRON, 46,(1990) N1, C. 3993-4002
  作者：NAJERA, CARMEN、SANSANO, JOSE MIGUEL

  DOI：——

  日期：——