t-butyl α-(p-tolylsulfinyl)acrylate | 191795-29-6

• 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: t-butyl α-(p-tolylsulfinyl)acrylate
• 英文别名: tert-butyl 2-[(S)-(4-methylphenyl)sulfinyl]prop-2-enoate
• CAS: 191795-29-6
• 化学式: C₁₄H₁₈O₃S
• 分子量: 266.361
• InChiKey: IMFNDWTWAQMMTO-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  t-butyl α-(p-tolylsulfinyl)acrylate 在 disodium hydrogenphosphate 、 四氧化锇 、 sodium amalgam 、 十二/十四烷基二甲基氧化胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 25.0 ℃ 、400.0 MPa 条件下， 反应 128.0h， 生成 (1S,2R,4R,5S,6R)-5,6-Dihydroxy-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates

  摘要：

  Enantiopure (S) benzyl and t-butyl 2-p-tolylsulfinylpropenoates (1 and 2) were readily prepared by Mannich condensation of (R) p-tolylsulfinylacetates (CH2O+Me2NH), followed by in situ nitrogen quaternization. These new chiral dienophiles reacted with furan at high pressures (4-13 Kbar) at rt to afford mainly a 2:1 mixture of both endo adducts (endo-B+endo-A). Enantiopure endo-4B and endo-4A were stereoselectively transformed into (+)-shikimic acid and (+)-5-epi-shikimic acid respectively, by dihydroxylation of the double bond, removal of the sulfinyl group, basic opening of the oxabicyclic skeleton and hydrolysis of the ester moiety. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00151-1
• 作为产物：
  描述：

  (+)-(RS)-(甲苯-4-亚磺酰基)-乙酸叔丁酯 在 calcium carbonate 、 碘甲烷 作用下， 以 水 、 乙腈 为溶剂， 反应 11.0h， 生成 t-butyl α-(p-tolylsulfinyl)acrylate
  参考文献：
  名称：

  Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates

  摘要：

  Enantiopure (S) benzyl and t-butyl 2-p-tolylsulfinylpropenoates (1 and 2) were readily prepared by Mannich condensation of (R) p-tolylsulfinylacetates (CH2O+Me2NH), followed by in situ nitrogen quaternization. These new chiral dienophiles reacted with furan at high pressures (4-13 Kbar) at rt to afford mainly a 2:1 mixture of both endo adducts (endo-B+endo-A). Enantiopure endo-4B and endo-4A were stereoselectively transformed into (+)-shikimic acid and (+)-5-epi-shikimic acid respectively, by dihydroxylation of the double bond, removal of the sulfinyl group, basic opening of the oxabicyclic skeleton and hydrolysis of the ester moiety. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00151-1

文献信息

• Asymmetric Cyclopropanation of Optically Active Vinyl Sulfoxides: A New Synthetic Approach to Biologically Active Compounds
  作者：Wanda H. Midura

  DOI：10.1080/10426500590911593

  日期：2005.3.2

  substituents on stereochemical course of cyclopropanation of vinyl sulfoxides with stabilized and nonstabilized ylides, as well as dependence on reaction conditions, was investigated. Application of optically active cyclopropanes obtained in the synthesis of conformationally constrained analogs of L-glutamic acid, the useful pharmacological tools in investigation of excitatory amino acid receptors, is presented

  摘要 研究了相邻取代基对乙烯基亚砜与稳定和非稳定叶立德环丙烷化立体化学过程的影响，以及对反应条件的依赖性。介绍了在合成受构象限制的 L-谷氨酸类似物中获得的光学活性环丙烷的应用，该类似物是研究兴奋性氨基酸受体的有用药理学工具。
• Enantioselective synthesis of (+)-shikimic acid and (+)-5-epi-shikimic acid by asymmetric Diels-Alder reaction of (S)-α-sulfinylacrylates
  作者：Javier Adrio、Juan C. Carretero、Jose L. García Ruano、Luisa M. Martín Cabrejas

  DOI：10.1016/s0957-4166(97)00151-1

  日期：1997.5

  Enantiopure (S) benzyl and t-butyl 2-p-tolylsulfinylpropenoates (1 and 2) were readily prepared by Mannich condensation of (R) p-tolylsulfinylacetates (CH2O+Me2NH), followed by in situ nitrogen quaternization. These new chiral dienophiles reacted with furan at high pressures (4-13 Kbar) at rt to afford mainly a 2:1 mixture of both endo adducts (endo-B+endo-A). Enantiopure endo-4B and endo-4A were stereoselectively transformed into (+)-shikimic acid and (+)-5-epi-shikimic acid respectively, by dihydroxylation of the double bond, removal of the sulfinyl group, basic opening of the oxabicyclic skeleton and hydrolysis of the ester moiety. (C) 1997 Elsevier Science Ltd.