methyl 4(R)-[(tert-butoxycarbonyl)amino]-oct-7-enoate

• 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: methyl 4(R)-[(tert-butoxycarbonyl)amino]-oct-7-enoate
• 英文别名: methyl (4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]oct-7-enoate
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: CAPYETPHKOXOFX-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-甲酯 在 咪唑 、 sodium tetrahydroborate 、 碘 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.54h， 生成 methyl 4(R)-[(tert-butoxycarbonyl)amino]-oct-7-enoate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure β- and γ-Amino Acid Derivatives Using Functionalized Organozinc Reagents

  摘要：

  beta-Amido zinc reagents 4 and 5 readily undergo beta-elimination when prepared in THF, but when a polar aprotic solvent such as DMF is employed, beta-elimination is suppressed. Using DMF, reaction of 4 with aryl iodides provides beta-homophenylalanine derivatives (12 examples, 20-89% yield), and analogous reactions of 5 give gamma-bishomophenylalanine derivatives (7 examples, 34-80% yield). The related zinc/copper reagents 17 and 18 are also useful intermediates that undergo subsequent cross-coupling reactions with a wide range of electrophiles (9 examples, 28-87% yield).

  DOI：

  10.1021/jo990941y

文献信息

• Synthesis of Enantiomerically Pure β- and γ-Amino Acid Derivatives Using Functionalized Organozinc Reagents
  作者：Charles S. Dexter、Richard F. W. Jackson、Jason Elliott

  DOI：10.1021/jo990941y

  日期：1999.10.1

  beta-Amido zinc reagents 4 and 5 readily undergo beta-elimination when prepared in THF, but when a polar aprotic solvent such as DMF is employed, beta-elimination is suppressed. Using DMF, reaction of 4 with aryl iodides provides beta-homophenylalanine derivatives (12 examples, 20-89% yield), and analogous reactions of 5 give gamma-bishomophenylalanine derivatives (7 examples, 34-80% yield). The related zinc/copper reagents 17 and 18 are also useful intermediates that undergo subsequent cross-coupling reactions with a wide range of electrophiles (9 examples, 28-87% yield).