(S_S,R)-(+)-dimethyl [2-oxo-4-(p-toluenesulfinylamino)-hex-5-enyl]-phosphonate | 667457-51-4

• 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_S,R)-(+)-dimethyl [2-oxo-4-(p-toluenesulfinylamino)-hex-5-enyl]-phosphonate
• 英文别名: dimethyl (S_S,R)-(+)-2-oxo-4-(p-toluenesulfinylamino)hex-5-enylphosphonate；(S)-N-[(3R)-6-dimethoxyphosphoryl-5-oxohex-1-en-3-yl]-4-methylbenzenesulfinamide
• CAS: 667457-51-4
• 化学式: C₁₅H₂₂NO₅PS
• 分子量: 359.383
• InChiKey: PDVMYQZYHSGUSV-NPMABZOXSA-N

物化性质

• 沸点：
  524.8±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S_S,R)-(+)-dimethyl [2-oxo-4-(p-toluenesulfinylamino)-hex-5-enyl]-phosphonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) sodium tetrahydroborate 、 cerium(III) chloride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 (+/-)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene
  参考文献：
  名称：

  Asymmetric Synthesis of the Carbocyclic Nucleoside Building Block (R)-(+)-4-Aminocyclopentenone Using δ-Amino β-Ketophosphonates and Ring-Closing Metathesis (RCM)

  摘要：

  Amino keto-2,7-dienes undergo ring-closing metathesis (RCM) to give 4-aminocyclopentenones, valuable intermediates in the asymmetric construction of carbocyclic nucleosides. The key amino ketodienes were prepared using delta-amino beta-ketophophonates, a new sulfinimine-derived chiral building block, and HWE chemistry.

  DOI：

  10.1021/ol049795v
• 作为产物：
  描述：

  (S)-(+)-N-(prop-2-enylidene)-p-toluenesulfinamide 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 6.25h， 生成 (S_S,R)-(+)-dimethyl [2-oxo-4-(p-toluenesulfinylamino)-hex-5-enyl]-phosphonate
  参考文献：
  名称：

  Asymmetric Synthesis of the Carbocyclic Nucleoside Building Block (R)-(+)-4-Aminocyclopentenone Using δ-Amino β-Ketophosphonates and Ring-Closing Metathesis (RCM)

  摘要：

  Amino keto-2,7-dienes undergo ring-closing metathesis (RCM) to give 4-aminocyclopentenones, valuable intermediates in the asymmetric construction of carbocyclic nucleosides. The key amino ketodienes were prepared using delta-amino beta-ketophophonates, a new sulfinimine-derived chiral building block, and HWE chemistry.

  DOI：

  10.1021/ol049795v

文献信息

• Asymmetric Synthesis of Cis-5-Substituted Pyrrolidine 2-Phosphonates Using Metal Carbenoid NH Insertion and δ-Amino β-Ketophosphonates
  作者：Franklin A. Davis、Yongzhong Wu、He Xu、Junyi Zhang

  DOI：10.1021/ol048157+

  日期：2004.11.1

  Cis-5-substituted pyrrolidine phosphonates, proline surrogates, are prepared by a highly stereoselective intramolecular metal carbenoid N-H insertion from a sulfinimine-derived delta-amino alpha-diazo beta-ketophosphonate.
• Asymmetric Synthesis of the Carbocyclic Nucleoside Building Block (<i>R</i>)-(+)-4-Aminocyclopentenone Using δ-Amino β-Ketophosphonates and Ring-Closing Metathesis (RCM)
  作者：Franklin A. Davis、Yongzhong Wu

  DOI：10.1021/ol049795v

  日期：2004.4.1

  Amino keto-2,7-dienes undergo ring-closing metathesis (RCM) to give 4-aminocyclopentenones, valuable intermediates in the asymmetric construction of carbocyclic nucleosides. The key amino ketodienes were prepared using delta-amino beta-ketophophonates, a new sulfinimine-derived chiral building block, and HWE chemistry.