(2S)-N-phthaloyl-2,3-dehydrovaline methyl ester | 26878-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2S)-N-phthaloyl-2,3-dehydrovaline methyl ester
• 英文别名: Methyl 1,3-dihydro-alpha-(1-methylethylidene)-1,3-dioxo-2H-isoindole-2-acetate；methyl 2-(1,3-dioxoisoindol-2-yl)-3-methylbut-2-enoate
• CAS: 26878-25-1
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: YROYZPBQBJYDGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (2S)-N-phthaloyl-3,4-dehydrovaline methyl ester 在 palladium diacetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 (2S)-N-phthaloyl-2,3-dehydrovaline methyl ester
  参考文献：
  名称：

  Kulokekahilide-1, a Cytotoxic Depsipeptide from the Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 mug/mL.

  DOI：

  10.1021/jo010176z

文献信息

• Neighbouring group effects promote substitution reactions over elimination and provide a stereocontrolled route to chloramphenicol
  作者：Christopher J. Easton、Craig A. Hutton、Martin C. Merrett、Edward R.T. Tiekink

  DOI：10.1016/0040-4020(96)00307-9

  日期：1996.5

  In reactions of β-brominated valine and p-nitrophenylalanine derivatives to give β-hydroxy amino acid derivatives the carboxyl group, when protected as an amide, exerts a neighbouring group effect to facilitate the substitution process, and reduce competing elimination reactions. As a consequence of the effect, the (2R,3R)- and (2R,3S)-stereoisomers of 3-bromo-N-tert-butyl-Nα-phthaloyl-p-nitrophenylalaninamide

  在β-溴化缬氨酸和对硝基苯丙氨酸衍生物反应生成β-羟基氨基酸衍生物的反应中，羧基作为酰胺被保护时，发挥邻近基团作用，以促进取代过程，并减少竞争性消除反应。作为效果的结果，（2 - [R，3 - [R ）-和（2 - [R，3小号）的3-溴-立体异构体ñ -叔丁基- ñ α -phthaloyl- p -nitrophenylalaninamide两者反应，得到（ 2小号，3 - [R）-3-羟基ñ -叔丁基- ñ α-邻苯二甲酰基-对-硝基苯丙氨酰胺，提供立体收敛的氯霉素途径。