(S_S,R)-(+)-methyl 3-(p-toluenesulfinylamino)-pent-4-enoate | 667457-50-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S_S,R)-(+)-methyl 3-(p-toluenesulfinylamino)-pent-4-enoate
• 英文别名: (R)-(+)-methyl 3-((S)-4-methylphenylsulfinamido)pent-4-enonate；methyl (3R)-3-[[(S)-(4-methylphenyl)sulfinyl]amino]pent-4-enoate
• CAS: 667457-50-3
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: FEUZXUDQVJJUSF-VOJFVSQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S_S,R)-(+)-methyl 3-(p-toluenesulfinylamino)-pent-4-enoate 在 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.25h， 生成 (S_S,R)-(+)-N-(p-toluenesulfinyl)-6-amino-4-oxo-octa-2,7-diene
  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：

  乙酸甲酯 、 (S)-(+)-N-(prop-2-enylidene)-p-toluenesulfinamide 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以87%的产率得到(S_S,R)-(+)-methyl 3-(p-toluenesulfinylamino)-pent-4-enoate
  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 <i>anti</i>-α-Substituted β-Amino Ketones from Sulfinimines
  作者：Franklin A. Davis、Peng Xu

  DOI：10.1021/jo2002352

  日期：2011.5.6

  Previously unknown, enantiopure, beta-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-alpha-substituted beta-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-alpha-substituted isomers which did. The anti-alpha-substituted beta-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-alpha-substituted beta-amino esters because alpha-alkylation of N-sulfinyl beta-amino Weinreb amide enolates resulted in poor diastereoselectivities.
• 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.