(1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>acetate | 145280-11-1

• 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: (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>acetate
• 英文别名: (1R,2S,5R)-menthyl-N-(tert-butyloxycarbonyl)-glycinate；(1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-[(tert-butoxycarbonyl)amino]acetate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 145280-11-1
• 化学式: C₁₇H₃₁NO₄
• 分子量: 313.437
• InChiKey: UPEQFIILOSSJPZ-HZSPNIEDSA-N

物化性质

• 沸点：
  404.0±28.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 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,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>acetate 在 sodium sulfate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.58h， 生成 {[1-(4-Cyano-phenyl)-meth-(Z)-ylidene]-amino}-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  First 1,3-Dipolar Cycloaddition of Azomethine Ylides with (E)-Ethyl 3-Fluoroacrylate: Regio- and Stereoselective Synthesis of Enantiopure ­Fluorinated Prolines

  摘要：

  通过偶氮甲基吡啶与 (E)-3- 氟丙烯酸乙酯的 1,3- 二极环加成反应，获得了具有四个手性中心的不纯氟化脯氨酸。

  DOI：

  10.1055/s-2006-933127
• 作为产物：
  描述：

  (-)-menthyl chloroacetate 在 氨 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2S,5R)-2-(1-methylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>acetate
  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

• Synthesis of nitroaryl derivatives of glycine via oxidative nucleophilic substitution of hydrogen in nitroarenes
  作者：Mieczysław Mąkosza、Mikołaj Chromiński、Daniel Sulikowski

  DOI：10.3998/ark.5550190.0012.608

  日期：——

  Carbanion of ethyl N-(1,3-dithiolan-2-ylidene)glycinate adds to activated nitroarenes mostly in para position to the nitro group. Subsequent oxidation of the resulting σ adducts with DDQ gave respective α-nitroarylated glycine derivatives in moderate yields. The reaction of esters of chiral alcohols such as (-)-menthol or (-)-8-phenylmenthol proceeds with a moderate or high diastereoselectivity leading

  N-(1,3-dithiolan-2-ylidene) 甘氨酸乙酯的碳负离子主要在硝基的对位添加到活化的硝基芳烃中。随后用 DDQ 氧化得到的 σ 加合物，得到相应的 α-硝基化甘氨酸衍生物，产率适中。手性醇的酯如 (-)-薄荷醇或 (-)-8-苯基薄荷醇的反应以中等或高的非对映选择性进行，导致对映体富集的硝基芳基甘氨酸。
• 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。
• Synthesis and Biological Activities of Conformationally Restricted Cyclopentenyl-Glutamate Analogues
  作者：Alison T. Ung、Karl Schafer、Karl B. Lindsay、Stephen G. Pyne、Kitti Amornraksa、Ria Wouters、Ilse Van der Linden、Ilse Biesmans、Anne S. J. Lesage、Brian W. Skelton、Allan H. White

  DOI：10.1021/jo010864i

  日期：2002.1.1

  An efficient method for preparing conformationally restricted cyclopentenyl-glutamate analogues in a regioselective and diastereoselective manner has been developed using a formal [3 + 2] cycloaddition reaction of dehydroamino acids. Methods for preparing optically active versions of these compounds have also been devised. Of these compounds, (S)-2 is an agonist at the mGlu5 (EC50 18 muM) and mGlu2 (EC50 45 muM) receptors.
• Synthesis and biological evaluation of menthol-based derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  作者：Bin Ye、Shawn Bauer、Brad O. Buckman、Ameen Ghannam、Brian D. Griedel、Seock-Kyu Khim、Wheeseong Lee、Karna L. Sacchi、Kenneth J. Shaw、Amy Liang、Qingyu Wu、Zuchun Zhao

  DOI：10.1016/s0960-894x(03)00686-3

  日期：2003.10

  Compound 1 was identified by high throughput screening as a novel PAI-1 inhibitor. Optimization of the B and C-segments of 1 resulted in a series of structurally simplified compounds with improved potency. The synthesis and SAR data of these compounds are presented here. (C) 2003 Elsevier Ltd. All rights reserved.