(S)-methyl-2-p-toluenesulfonylamido-2-methyl-4-pentenoate | 225656-35-9

• 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: (S)-methyl-2-p-toluenesulfonylamido-2-methyl-4-pentenoate
• 英文别名: methyl (S)-2-methyl-2-(toluenesulfonylamino)-4-pentenoate；methyl (2S)-2-methyl-2-[(4-methylphenyl)sulfonylamino]pent-4-enoate
• CAS: 225656-35-9
• 化学式: C₁₄H₁₉NO₄S
• 分子量: 297.375
• InChiKey: HKITVOKRCUMPJI-AWEZNQCLSA-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：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl-2-p-toluenesulfonylamido-2-methyl-4-pentenoate 在 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 N-[(3S,5R)-5-(iodomethyl)-3-methyl-2-oxooxolan-3-yl]-4-methylbenzenesulfonamide 、 N-[(3S,5S)-5-(iodomethyl)-3-methyl-2-oxooxolan-3-yl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Stereoselective Iodocyclization of (S)-Allylalanine Derivatives:  γ-Lactone vs Cyclic Carbamate Formation

  摘要：

  An efficient procedure for highly chemo- and stereoselective cyclization of (S)-allylalanine derivatives is reported (diastereomeric ratios up to 96:4) where the reaction course can be completely controlled by switching from gamma-lactones to cyclic carbamates simply with the proper choice of the amino acid protecting groups. Both processes are stereoconvergent and afford the (S,S)-products in high yields, short reaction times, and mild reaction conditions.

  DOI：

  10.1021/ol070764k
• 作为产物：
  描述：

  (S)-(-)-α-烯丙基丙氨酸 在 氯化亚砜 、 四甲基乙二胺 作用下， 以 乙腈 为溶剂， 反应 90.0h， 生成 (S)-methyl-2-p-toluenesulfonylamido-2-methyl-4-pentenoate
  参考文献：
  名称：

  Stereoselective Iodocyclization of (S)-Allylalanine Derivatives:  γ-Lactone vs Cyclic Carbamate Formation

  摘要：

  An efficient procedure for highly chemo- and stereoselective cyclization of (S)-allylalanine derivatives is reported (diastereomeric ratios up to 96:4) where the reaction course can be completely controlled by switching from gamma-lactones to cyclic carbamates simply with the proper choice of the amino acid protecting groups. Both processes are stereoconvergent and afford the (S,S)-products in high yields, short reaction times, and mild reaction conditions.

  DOI：

  10.1021/ol070764k

文献信息

• Synthesis of Enantiopure Functionalized Pipecolic Acids via Amino Acid DerivedN-Acyliminium Ions
  作者：Floris P. J. T. Rutjes、Johan J. N. Veerman、Wim J. N. Meester、Henk Hiemstra、Hans E. Schoemaker

  DOI：10.1002/(sici)1099-0690(199905)1999:5<1127::aid-ejoc1127>3.0.co;2-a

  日期：1999.5

  The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.
• Stereoselective Iodocyclization of (<i>S</i>)-Allylalanine Derivatives:  γ-Lactone vs Cyclic Carbamate Formation
  作者：Mariella Pattarozzi、Cristiano Zonta、Quirinus B. Broxterman、Bernard Kaptein、Rita De Zorzi、Lucio Randaccio、Paolo Scrimin、Giulia Licini

  DOI：10.1021/ol070764k

  日期：2007.6.1

  An efficient procedure for highly chemo- and stereoselective cyclization of (S)-allylalanine derivatives is reported (diastereomeric ratios up to 96:4) where the reaction course can be completely controlled by switching from gamma-lactones to cyclic carbamates simply with the proper choice of the amino acid protecting groups. Both processes are stereoconvergent and afford the (S,S)-products in high yields, short reaction times, and mild reaction conditions.