(1R,3R,4S)-menthyl 2-bromo-N-t-BOC-glycinate

• 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: (1R,3R,4S)-menthyl 2-bromo-N-t-BOC-glycinate
• 英文别名: (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>bromoacetate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• 化学式: C₁₇H₃₀BrNO₄
• 分子量: 392.334
• InChiKey: GHJIYAHXXMYEAP-RBKKPWLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S)-menthyl 2-bromo-N-t-BOC-glycinate 在 肼 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 (1R,3R,4S)-menthyl (2S)-N-t-BOC-2-(3,5-dimethyl-4-pyrazolyl)glycinate
  参考文献：
  名称：

  A radical-organometallic glycine synthon. Preparation of homochiral heterocyclic α-amino acids

  摘要：

  Co)Acac)2 reacts with (1) and (d)-menthyl N-BOC-2-bromoglycinates to give (1)- and (d)-menthyl N-BOC 3-acetylnorvalinates, which are converted into homochiral 2-(3,5-dimethyl-4-pyrazolyl)glycine and 2-(3,5-dimethyl)-4-isoxazolylglycine.

  DOI：

  10.1016/s0040-4039(00)61614-3
• 作为产物：
  描述：

  (-)-menthyl chloroacetate 在 N-溴代丁二酰亚胺(NBS) 、 氨 作用下， 以 四氯化碳 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,3R,4S)-menthyl 2-bromo-N-t-BOC-glycinate
  参考文献：
  名称：

  A radical-organometallic glycine synthon. Preparation of homochiral heterocyclic α-amino acids

  摘要：

  Co)Acac)2 reacts with (1) and (d)-menthyl N-BOC-2-bromoglycinates to give (1)- and (d)-menthyl N-BOC 3-acetylnorvalinates, which are converted into homochiral 2-(3,5-dimethyl-4-pyrazolyl)glycine and 2-(3,5-dimethyl)-4-isoxazolylglycine.

  DOI：

  10.1016/s0040-4039(00)61614-3

文献信息

• The asymmetric synthesis of α-amino acids via the addition of grignard reagents to imine derivatives.
  作者：David P.G. Hamon、Ralph A. Massy-Westropp、Pasquale Razzino

  DOI：10.1016/s0040-4020(01)90125-5

  日期：1992.1

  ester-8-phenylmenthyl N-Boc-glycinate 5a, undergoes free radical bromination by N-bromosuccinimide to give 8-phenylmenthyl N-Boc-bromoglycinate 8. Treatment of the bromide 8 with a variety of Grignard reagents at low temperature gave 8-phenylmenthyl (S-N-Boc-2-alkylglycinates with high diastereoselectivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant

  酯-8-苯基薄荷基N -Boc-甘氨酸酸酯5a通过N-溴琥珀酰亚胺进行自由基溴化，得到8-苯基薄荷基N -Boc-溴甘氨酸酸酯8。在低温下用各种格氏试剂对溴化物8进行处理，得到了具有高非对映选择性的8-苯基薄荷基（S - N -Boc-2-烷基甘氨酸），发现了水解这些衍生物的条件，而得到的氨基酸没有外消旋化。
• Asymmetric induction in radical reactions: enantioselective syntheses of (S)-2-deuterioglycine and (R)-2-deuterioglycine
  作者：David P. G. Hamon、Pasquale Razzino、Ralph A. Massy-Westropp

  DOI：10.1039/c39910000332

  日期：——

  The (–)-8-phenylmenthol ester of N-Boc-glycine is brominated with N-bromosuccinimide and the bromo-compound is reduced with tri-n-butyldeuteriostannane to give the chiral glycine derivative in high optical yield which upon hydrolysis yields the amino acid without racemisation.

  N-Boc 甘氨酸的(-)-8-苯基薄荷醇酯用 N-溴代丁二酰亚胺溴化，溴代化合物用三-正丁基氚基锡烷还原，得到手性甘氨酸衍生物，光学产率高，水解后得到的氨基酸无外消旋化。
• A radical-organometallic glycine synthon. Preparation of homochiral heterocyclic α-amino acids
  作者：María E. Lloris、Marcial Moreno-Mañas

  DOI：10.1016/s0040-4039(00)61614-3

  日期：1993.10

  Co)Acac)2 reacts with (1) and (d)-menthyl N-BOC-2-bromoglycinates to give (1)- and (d)-menthyl N-BOC 3-acetylnorvalinates, which are converted into homochiral 2-(3,5-dimethyl-4-pyrazolyl)glycine and 2-(3,5-dimethyl)-4-isoxazolylglycine.