(2S,5S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-4-oxo-6-phenyl-hexanoic acid methyl ester | 153077-93-1

• 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: (2S,5S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-4-oxo-6-phenyl-hexanoic acid methyl ester
• CAS: 153077-93-1
• 化学式: C₂₂H₂₁NO₅
• 分子量: 379.412
• InChiKey: WYHLENWYQVDIDH-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.75
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,5S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-4-oxo-6-phenyl-hexanoic acid methyl ester 在 sodium tetrahydroborate 作用下， 生成 (2S,4R,5S)-4-Hydroxy-5-(2-hydroxymethyl-benzoylamino)-2-methyl-6-phenyl-hexanoic acid methyl ester 、 (2S,4S,5S)-4-Hydroxy-5-(2-hydroxymethyl-benzoylamino)-2-methyl-6-phenyl-hexanoic acid methyl ester
  参考文献：
  名称：

  A new synthetic route for the γ-lactone precursors of hydroxyethylene dipeptide isosteres

  摘要：

  Delta-Phthalimido-gamma-ketoesters were obtained by the Pd catalyzed coupling reaction between acid chlorides and organozinc reagents derived from beta-iodoesters, and were converted into the gamma-lactone precursors of Phe-psi[H.E.]-Ala and Phe-psi[H.E.]-Pro (15a,b-18a,b).

  DOI：

  10.1016/s0040-4039(00)73819-6
• 作为产物：
  描述：

  (S)-(+)-3-羟基异丁酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 铜 、 锌 作用下， 反应 1.33h， 生成 (2S,5S)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-4-oxo-6-phenyl-hexanoic acid methyl ester
  参考文献：
  名称：

  A new synthetic route for the γ-lactone precursors of hydroxyethylene dipeptide isosteres

  摘要：

  Delta-Phthalimido-gamma-ketoesters were obtained by the Pd catalyzed coupling reaction between acid chlorides and organozinc reagents derived from beta-iodoesters, and were converted into the gamma-lactone precursors of Phe-psi[H.E.]-Ala and Phe-psi[H.E.]-Pro (15a,b-18a,b).

  DOI：

  10.1016/s0040-4039(00)73819-6