(S)-3-p-tolylsulfinylbut-3-en-2-ol | 235100-20-6

• 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-p-tolylsulfinylbut-3-en-2-ol
• 英文别名: (S)_S-3-p-tolylsulfinyl-3-buten-2-ol；(Ss)-3-hydroxy-1-buten-2-yl p-tolyl sulfoxide；3-[(S)-(4-methylphenyl)sulfinyl]but-3-en-2-ol
• CAS: 235100-20-6
• 化学式: C₁₁H₁₄O₂S
• 分子量: 210.297
• InChiKey: GGAXHHAZXAANRJ-IWSPRGBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (S)-3-p-tolylsulfinylbut-3-en-2-ol 在 jones reagent 作用下， 以42%的产率得到(S_S)-3-(p-tolylsulfinyl)-3-buten-2-one
  参考文献：
  名称：

  Stereocontrolled Asymmetric Synthesis of Optically Active Acylcyclopropane Derivatives by Michael Additions of Bromomalonate to Chiral .ALPHA.-Acylvinylic Sulfoxides.

  摘要：

  溴丙二酸根阴离子与手性α-酰基烯烃磺氧化物的迈克尔加成及随后发生的分子内烷基化反应，生成了具有高对映体过量的光学活性酰基环丙烷衍生物。产物的立体化学通过与已知绝对构型化合物的化学关联进行确定。根据获得的立体化学结果，推测出了不对称诱导的机制。

  DOI：

  10.1248/cpb.42.985
• 作为产物：
  描述：

  (R)_S-dimethylamino-2 p-tolylsulfinyl-1 ethane 在 sodium hydroxide 、 甲基锂 、 碘甲烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 (S)-3-p-tolylsulfinylbut-3-en-2-ol
  参考文献：
  名称：

  Acces aux (R)S acyl-1 vinyl -tolylsulfoxydes a partir du (R)S dimethylamino-2 -tolylsulfinyl-1 ethane. Leurs reactivites en tant que dienophile.

  摘要：

  DOI：

  10.1016/s0040-4039(00)84595-5

文献信息

• Stereocontrolled Asymmetric Synthesis of Optically Active Acylcyclopropane Derivatives by Michael Additions of Bromomalonate to Chiral .ALPHA.-Acylvinylic Sulfoxides.
  作者：Kunio HIROI、Yoshihisa ARINAGA

  DOI：10.1248/cpb.42.985

  日期：——

  Michael addition of bromomalonate carbanions to chiral α-acylvinylic sulfoxides and the subsequent intramoleculer alkylation yielded optically active acylcyclopropane derivatives with high enantiomeric excess. Stereochemistry of the product was determined by chemical correlation to a compound of known absolute configuration. The mechanism for the asymmetric induction is deduced on the basis of the stereochemical results obtained.

  溴丙二酸根阴离子与手性α-酰基烯烃磺氧化物的迈克尔加成及随后发生的分子内烷基化反应，生成了具有高对映体过量的光学活性酰基环丙烷衍生物。产物的立体化学通过与已知绝对构型化合物的化学关联进行确定。根据获得的立体化学结果，推测出了不对称诱导的机制。
• A Facile One-Pot Synthesis of 1-Acyl and 1-α-Hydroxyalkylvinyl<i>p</i>-Tolyl (<i>S</i>)-Sulfoxides
  作者：Christian Alexandre、Omar Belkadi、Christian Maignan

  DOI：10.1055/s-1992-26161

  日期：——

  A novel chiral intermediate, 2-ethoxyethyl p-tolyl sulfoxide (4), permits access in one step to optically active α-methylene-β-oxo sulfoxides, which are very useful dienophiles.

  一种新型手性中间体，2-乙氧基乙基对甲苯基亚磺氧化物（4），能在一步中获得光学活性的α-亚甲基-β-氧杂磺酮，这些化合物是非常有用的二烯亲和体。
• Stereoselective hydrogenation of α-sulfinyl radical generated from alkyl radical addition to α-(1-hydroxyethyl)vinyl sulfoxide
  作者：Nobuyuki Mase、Shutaro Wake、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1016/s0040-4039(98)01118-6

  日期：1998.7

  The reaction of (2S,S-S)-alpha-(1-hydroxyethyl)vinyl sulfoxide with alkyl radicals and tributyltin hydride gave the addilion-hydrogenation products with high diastereoselectivity, whereas (2R,S-S)-alpha-(-1-hydroxyethyl)vinyl sulfoxide gave no products under similar conditions. An important role of intramolecular hydrogen bonding for the diastereoselectivity as well as the reactivity toward alkyl radicals is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An easy synthesis of chiral sulfinyl allylic bromides and their use in the preparation of(R)S- and (S)S-2-p-tolylsulfinyl-1,3-alkadienes
  作者：Eric Bonfand、Pascal Gosselin、Christian Maignan

  DOI：10.1016/s0957-4166(00)80374-2

  日期：1993.7

  Condensation of (R)-vinyl-p-tolylsulfoxide anion on carbonyl compounds led directly to chiral allylic sulfinylalcohols 1. By treatment with NBS/Me2S, these alcohols 1 were converted into the rearranged primary allylic bromides 2 via SN2' displacement. Optically pure (R)- and (S)-2-p-tolylsulfinyl-1,3-alkadienes 3 resulted from the action of KOH/ROH upon these bromides 2 via E2' eliminations.
• First syntheses of chiral 2-sulfinylbutadienes
  作者：Eric Bonfand、Pascal Gosselin、Christian Maignan

  DOI：10.1016/s0040-4039(00)74207-9

  日期：1992.4

  The title compounds were readily prepared respectively from (S)-3-p-tolylsulfinylbut-3-en-2-ol 3 and (S)-3-p-tolylsulfinylbul-3-en-2-one 4.