(R)-1-(but-3-ene-1-sulfinyl)-4-methyl-benzene | 115878-98-3

• 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: (R)-1-(but-3-ene-1-sulfinyl)-4-methyl-benzene
• 英文别名: (R)-p-tolyl sulfoxide；1-[(R)-but-3-enylsulfinyl]-4-methylbenzene
• CAS: 115878-98-3
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: RFBUOJOYPCZSEH-CYBMUJFWSA-N

物化性质

• 沸点：
  323.5±31.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(but-3-ene-1-sulfinyl)-4-methyl-benzene 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.2h， 生成 (2R,3R)-1-diethoxyphosphoryl-1,1-difluoro-3-[(R)-(4-methylphenyl)sulfinyl]hex-5-en-2-ol
  参考文献：
  名称：

  Synthesis of 3′-Arylsulfonyl-4′-[(diethoxyphosphoryl)difluoromethyl]thymidine

  摘要：

  DOI：

  10.1055/s-1998-4501
• 作为产物：
  描述：

  4-溴-1-丁烯 、 (-)-menthyl p-toluenesulfinate 在 碘 、 magnesium 作用下， 生成 (R)-1-(but-3-ene-1-sulfinyl)-4-methyl-benzene
  参考文献：
  名称：

  Asymmetric synthesis of gem-chlorofluorocyclopentane derivatives by intramolecular trapping of dihaloalkyl radicals

  摘要：

  Radical promoted cyclization of enantiomerically pure substituted 1,1-dichloro-1-fluoro-3-[(4-methylphenyl)sulfinyl]hex-5-en-2-ols (6) afforded the title compounds 12 in good overall yields. The regio and stereochemical outcome of the cyclizations are explained by considering the respective transition states. The structure and configuration of the products were elucidated with the aid of H-1, C-13 and F-19 NMR spectra and H-1-{H-1} and H-1-{F-19} NOE difference experiments.

  DOI：

  10.1016/s0040-4020(01)80430-0

文献信息

• Highly diastereoselective methylene transfer from diazomethane to the carbonyl of β-keto sulfoxides. A general approach to synthetically versatile fluorine-containing chiral building blocks
  作者：Alberto Arnone、Pierfrancesco Bravo、Massimo Frigerio、Fiorenza Viani、Vadim A. Soloshonok

  DOI：10.1016/s0040-4020(98)83043-3

  日期：1998.9

  afford the corresponding diastereo- and enantiomerically pure epoxides. A plausible mechanistic rationale for the origin of the stereochemical preferences in these reactions has been provided. Synthetic versatility of the resultant epoxides has been demonstrated by a series of key transformations of the epoxide ring and the sulfinyl group including ring-opening, reductive desulfurization and syn-elimination

  本文描述了重氮甲烷与在末端位点带有二氟，三氟和二氟氯甲基的α-烷基和α-苯基取代的（R S）-β-酮亚砜的反应，从而提供了相应的非对映体和对映体纯的环氧化物。提供了对于这些反应中立体化学偏好的起源的合理的机械原理。通过环氧化物环和亚磺酰基的一系列关键转化，包括开环，还原脱硫和合成消除反应，已证明了所得环氧化物的合成用途广泛。
• Total synthesis of a pepstatin analog incorporating two trifluoromethyl hydroxymethylene isosteres (Tfm-GABOB) and evaluation of Tfm-GABOB containing peptides as inhibitors of HIV-1 protease and MMP-9
  作者：Cristina Pesenti、Alberto Arnone、Stefano Bellosta、Pierfrancesco Bravo、Monica Canavesi、Eleonora Corradi、Massimo Frigerio、Stefano V Meille、Mara Monetti、Walter Panzeri、Fiorenza Viani、Romina Venturini、Matteo Zanda

  DOI：10.1016/s0040-4020(01)00543-9

  日期：2001.7

  We describe the asymmetric total synthesis of a trifluoromethyl (Tfm) analogue of the aspartate protease inhibitor pepstatin incorporating two γ-Tfm-γ-amino-β-hydroxybutyric acid (γ-Tfm-GABOB) units instead of the natural statine units. The title compound as well as several Tfm-substituted precursors were tested as inhibitors of HIV-1 protease and Gelatinase B (MMP-9)

  我们描述了天冬氨酸蛋白酶抑制剂胃抑素的三氟甲基（Tfm）类似物的不对称总合成，该蛋白结合了两个γ-Tfm-γ-氨基-β-羟基丁酸（γ-Tfm-GABOB）单元而不是天然他汀类单元。测试了标题化合物以及几种Tfm取代的前体作为HIV-1蛋白酶和明胶酶B（MMP-9）的抑制剂
• Bravo, Pierfrancesco; Ganazzoli, Fabio; Resnati, Giuseppe, Journal of Chemical Research, Miniprint, 1988, # 7, p. 1701 - 1739
  作者：Bravo, Pierfrancesco、Ganazzoli, Fabio、Resnati, Giuseppe、Munari, Sergio De、Albinati, Alberto

  DOI：——

  日期：——
• Bravo, Pierfrancesco; Piovosi, Elena; Resnati, Giuseppe, Gazzetta Chimica Italiana, 1988, vol. 118, # 2, p. 115 - 122
  作者：Bravo, Pierfrancesco、Piovosi, Elena、Resnati, Giuseppe、Munari, Sergio De

  DOI：——

  日期：——
• Synthesis of (+)- and (−)-Statine via Chiral Sulfoxide Chemistry
  作者：Cristina Pesenti、Pierfrancesco Bravo、Eleonora Corradi、Massimo Frigerio、Stefano V. Meille、Walter Panzeri、Fiorenza Viani、Matteo Zanda

  DOI：10.1021/jo010383z

  日期：2001.8.1