(RS)-1-(N-tosylpyrrol-2-yl)but-3-en-1-ol | 137480-06-9

• 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: (RS)-1-(N-tosylpyrrol-2-yl)but-3-en-1-ol
• 英文别名: 1-(1-(4-methylphenylsulfonyl)-1H-pyrrol-2-yl)-3-buten-1-ol；1-(1-tosyl-1H-pyrrol-2-yl)-3-buten-1-ol；1-[1-(4-methylphenyl)sulfonylpyrrol-2-yl]but-3-en-1-ol
• CAS: 137480-06-9
• 化学式: C₁₅H₁₇NO₃S
• 分子量: 291.371
• InChiKey: HAPRCYRXMIIMCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-1-(N-tosylpyrrol-2-yl)but-3-en-1-ol 生成 (R)-1-(N-tosylpyrrol-2-yl)but-3-en-1-ol
  参考文献：
  名称：

  使用改良的Sharpless不对称环氧化试剂通过动力学拆分制备旋光性α-吡咯甲醇

  摘要：

  通过使用改良的Sharpless不对称环氧化试剂进行α-吡咯甲醇的动力学拆分，得到具有高对映选择性（> 90％ee ）的慢反应对映体（R）-3 a-f和（S）-3b，d ）和较高的化学收率（30-43％）。

  DOI：

  10.1016/s0957-4166(00)80455-3
• 作为产物：
  描述：

  2-丙烯基锂 、 1-(对甲苯磺酰)吡咯-2-甲醛 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到(RS)-1-(N-tosylpyrrol-2-yl)but-3-en-1-ol
  参考文献：
  名称：

  Zhou, Wei-Shan; Wei, Dong, Journal of Chemical Research, Miniprint, 1993, # 8, p. 1971 - 1980

  摘要：

  DOI：

文献信息

• Catalytic Nucleophilic Allylation Driven by the Water–Gas Shift Reaction
  作者：Scott E. Denmark、Zachery D. Matesich、Son T. Nguyen、Selena Milicevic Sephton

  DOI：10.1021/acs.joc.7b02658

  日期：2018.1.5

  of this reaction from the initial serendipitous discovery to its general synthetic scope is detailed, highlighting the roles of water, CO, and amine in the generation of a more complete catalytic cycle. The use of unsymmetrical allylic pro-nucleophiles was shown to give preferential product formation through the modulation of reaction conditions. Both (E)-cinnamyl acetate and vinyl oxirane were efficiently

  钌与烯丙基亲核试剂的醛催化烯丙基化已被证明是在温和条件下形成碳-碳键的有效方法。此反应从最初的偶然发现到其一般合成范围的演变过程都进行了详细介绍，突出了水，一氧化碳和胺在更完整的催化循环生成中的作用。结果表明，使用不对称的烯丙基亲核亲核试剂可以通过调节反应条件来优先形成产物。（E）-肉桂酸乙酸酯和乙烯基环氧乙烷均有效地用于形成抗支链产物（抗/ syn最高> 20：1 ）和E-线性产物（最高> 20：1 E / s ）Z）分别与芳香族，α，β-不饱和和脂肪族醛形成高选择性。强调了使反应对映选择性的尝试，包括对苯甲醛高达75:25的对映富集。
• Method for Forming Allylic Alcohols
  申请人：Denmark Scott E.

  公开号：US20140031562A1

  公开（公告）日：2014-01-30

  A method of performing a chemical reaction includes reacting an allyl donor and a substrate in a reaction mixture, and forming a homoallylic alcohol in the reaction mixture. The substrate may be an aldehyde or a hemiacetal. The reaction mixture includes a ruthenium catalyst, carbon monoxide at a level of at least 1 equivalent relative to the substrate, and water at a level of at least 1 equivalent relative to the substrate, and an amine at a level of from 0 to 0.5 equivalent relative to the substrate. The reaction mixture may also include a halide, and the equivalents of the amine may be similar to those of the halide. The reacting includes maintaining the reaction mixture at a temperature of at least 40° C. The method may be catalytic in metal, environmentally benign, amenable to large-scale applications, and applicable to a wide range of substrates.

  一种进行化学反应的方法包括在反应混合物中反应烯丙基供体和底物，并在反应混合物中形成同烯丙基醇。底物可以是醛或半缩醛。反应混合物包括一种钌催化剂，一定量的一氧化碳（相对于底物至少1当量），一定量的水（相对于底物至少1当量）和一定量的胺（相对于底物从0到0.5当量）。反应混合物还可以包括卤化物，胺的当量可以与卤化物的当量类似。反应包括将反应混合物保持在至少40°C的温度下。该方法可能是金属催化的，对环境友好，适用于大规模应用，并适用于广泛的底物范围。
• Catalytic, Nucleophilic Allylation of Aldehydes with Allyl Acetate
  作者：Scott E. Denmark、Son T. Nguyen

  DOI：10.1021/ol8028725

  日期：2009.2.5

  A new catalytic allylation of aldehydes has been developed that employs allyl acetate as the allylating reagent. Under catalysis by ruthenium trichloride (3 mol %) in the presence of carbon monoxide (30 psi), water (1.5 equiv), and triethylamine (0.1 equiv), a wide range of aromatic, olefinic, and aliphatic aldehydes are efficiently allylated under mild conditions (70 degrees C, 24-48 h). The stoichiometric byproducts of this reaction are carbon dioxide and acetic acid.
• [EN] METHOD FOR FORMING ALLYLIC ALCOHOLS<br/>[FR] PROCÉDÉ DE FORMATION D'ALCOOLS ALLYLIQUES
  申请人：UNIV ILLINOIS

  公开号：WO2010025366A2

  公开（公告）日：2010-03-04

  A method of performing a chemical reaction includes reacting an allyl donor and a substrate in a reaction mixture, and forming a homoallylic alcohol in the reaction mixture. The substrate may be an aldehyde or a hemiacetal. The reaction mixture includes a ruthenium catalyst, carbon monoxide at a level of at least 1 equivalent relative to the substrate, and water at a level of at least 1 equivalent relative to the substrate, and an amine at a level of from 0 to 0.5 equivalent relative to the substrate. The reaction mixture may also include a halide, and the equivalents of the amine may be similar to those of the halide. The reacting includes maintaining the reaction mixture at a temperature of at least 40°C. The method may be catalytic in metal, environmentally benign, amenable to large-scale applications, and applicable to a wide range of substrates.