tert-butyl 4,4-diethoxy-2-p-tolylsulfinylbut-2-enoate | 149035-05-2

• 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: tert-butyl 4,4-diethoxy-2-p-tolylsulfinylbut-2-enoate
• CAS: 149035-05-2
• 化学式: C₁₉H₂₈O₅S
• 分子量: 368.494
• InChiKey: VYDNOWIQQKNOKQ-BEWKRWDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4,4-diethoxy-2-p-tolylsulfinylbut-2-enoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 (1R,2R,5R,6S,7S)-5-Ethoxy-2-(toluene-4-sulfinyl)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of γ-alkoxy-α-sulfinylbutenolides

  摘要：

  The synthesis of the enantiomerically pure 5-ethoxy-3-p-tolylsulfinyl-2(5H)-furanones (2a and 2b) and the study of their behaviour as dienophiles in asymmetric Diels-Alder reactions with cyclopentadiene arc reported. Depending on the reaction conditions, the pi-facial selectivity is mainly controlled by the sulfur or C-5 configurations.

  DOI：

  10.1016/s0957-4166(00)82331-9
• 作为产物：
  描述：

  2,2-二乙氧基乙醛 、 (+)-(RS)-(甲苯-4-亚磺酰基)-乙酸叔丁酯 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 60.0h， 生成 tert-butyl 4,4-diethoxy-2-p-tolylsulfinylbut-2-enoate 、 (Z)-4,4-Diethoxy-2-((S)-toluene-4-sulfinyl)-but-2-enoic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of γ-alkoxy-α-sulfinylbutenolides

  摘要：

  The synthesis of the enantiomerically pure 5-ethoxy-3-p-tolylsulfinyl-2(5H)-furanones (2a and 2b) and the study of their behaviour as dienophiles in asymmetric Diels-Alder reactions with cyclopentadiene arc reported. Depending on the reaction conditions, the pi-facial selectivity is mainly controlled by the sulfur or C-5 configurations.

  DOI：

  10.1016/s0957-4166(00)82331-9

文献信息

• Asymmetric Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinoline Derivatives by 1,3-Dipolar Cycloadditions of Stabilized Isoquinolinium<i>N</i>-Ylides with Sulfinyl Dipolarophiles
  作者：José Luis García Ruano、Alberto Fraile、M. Rosario Martín、Gemma González、Cristina Fajardo、Ana María Martín-Castro

  DOI：10.1021/jo200191c

  日期：2011.5.6

  Enantiomerically pure pyrrolo[2,1-a]isoquinoline derivatives are obtained by 1,3-dipolar reactions of isoquinolinium azomethine ylides with enantiopure 3-p-tolylsulfinylacrylonitriles, tert-butyl (2E)-4,4-diethoxy-2-p-tolylsulfinylbut-2-enoate, and 5-ethoxy-3-p-tolylsulfinylfuran-2(5H)-ones. Reactions evolve through the anti conformation of the ylide with complete regioselectivity. The facial selectivity is completely controlled by the configuration of the sulfinyl sulfur for acyclic dipolarophiles, whereas it is high (dr 83/17 or 89/11) but controlled by the C-5 configuration for sulfinylfuranones. Complete endo selectivity is observed with cyclic dipolarophiles and substituted acrylonitriles, but it is low with butenoate. The sulfinyl group also exerts a positive influence on the dipolarophilic reactivity toward these ylides.