(+/-)-N-tert-butoxycarbonyl-α-1-naphthylglycine methyl ester | 896132-09-5

• 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: (+/-)-N-tert-butoxycarbonyl-α-1-naphthylglycine methyl ester
• 英文别名: methyl 2-(tert-butoxycarbonylamino)-2-(naphthalen-1-yl)acetate；(RS)-methyl 2-(tert-butoxycarbonylamino)-2-(naphthalen-1-yl)acetate；Methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-naphthalen-1-ylacetate；methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-naphthalen-1-ylacetate
• CAS: 896132-09-5
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: LSOWJAVZROFOJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (+/-)-N-tert-butoxycarbonyl-α-1-naphthylglycine methyl ester 在 sodium tetrahydroborate 、 lithium chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 生成 4-(1-Naphthyl)-2-oxazolidone
  参考文献：
  名称：

  Kinetic Resolution of 2-Oxazolidinones via Catalytic, Enantioselective N-Acylation

  摘要：

  Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities.

  DOI：

  10.1021/ja061560m
• 作为产物：
  描述：

  2-amino-2-(naphthalen-1-yl)acetonitrile 在 盐酸 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (+/-)-N-tert-butoxycarbonyl-α-1-naphthylglycine methyl ester
  参考文献：
  名称：

  Kinetic Resolution of 2-Oxazolidinones via Catalytic, Enantioselective N-Acylation

  摘要：

  Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities.

  DOI：

  10.1021/ja061560m

文献信息

• One-Pot Synthesis of α-Amino Acids from CO₂ Using a Bismetal Reagent with Si–B Bond
  作者：Tsuyoshi Mita、Jianyang Chen、Masumi Sugawara、Yoshihiro Sato

  DOI：10.1021/ol302952r

  日期：2012.12.21

  TsOH·H2O, precursors of N-Boc-imines can be converted into the corresponding α-aryl or α-alkenyl glycine derivatives under gaseous CO2 in moderate-to-high yields with a single operation. α-Isobutenyl glycine thus obtained can be further derivatized into various types of α-amino acids including N-Boc-leucine, serine, and glycine derivatives in short steps.

  在1.1当量的PhMe 2 Si-Bpin，5当量的CsF和20摩尔％的TsOH·H 2 O存在下，N -Boc-亚胺的前体可以转化为相应的α-芳基或α-烯基甘氨酸一次操作即可在气态CO 2下以中等至高收率得到各种衍生物。由此获得的α-异丁烯基甘氨酸可以在短时间内进一步衍生为各种类型的α-氨基酸，包括N -Boc-亮氨酸，丝氨酸和甘氨酸衍生物。
• One-Pot Synthesis of α-Amino Acids from Imines through CO2 Incorporation: An Alternative Method for Strecker Synthesis
  作者：Tsuyoshi Mita、Jianyang Chen、Masumi Sugawara、Yoshihiro Sato

  DOI：10.1002/anie.201006422

  日期：2011.2.7

  It′s a gas: A novel one‐pot process for the synthesis of α‐amino acids from imine equivalents using CO2 gas as a carbon source has been developed. This reaction was made possible by the reagent combination of TMSSnBu3 and CsF (see scheme). Three successive reactions (imine formation, stannylation, and carboxylation) proceeded in the same flask under these conditions to give products in up to 79 % yield

  它是一种气体：已开发出一种新颖的单罐方法，该方法使用CO 2气体作为碳源，从亚胺当量合成α-氨基酸。通过TMSSnBu 3和CsF的试剂结合使该反应成为可能（参见方案）。在这些条件下，在同一烧瓶中进行了三个连续的反应（亚胺形成，甲氧基化和羧化），以最高79％的收率得到产物。Boc =叔丁氧羰基，TMS =三甲基甲硅烷基。
• Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides
  作者：Pranjal K. Baruah、Jason Dinsmore、Amber M. King、Christophe Salomé、Marc De Ryck、Rafal Kaminski、Laurent Provins、Harold Kohn

  DOI：10.1016/j.bmc.2012.04.002

  日期：2012.6

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of Arylglycine and Mandelic Acid Derivatives through Carboxylations of α-Amido and α-Acetoxy Stannanes with Carbon Dioxide
  作者：Tsuyoshi Mita、Masumi Sugawara、Hiroyuki Hasegawa、Yoshihiro Sato

  DOI：10.1021/jo202597p

  日期：2012.3.2

  Incorporation reactions of carbon dioxide (CO2) with N-Boc-alpha\-amido and a-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected alpha-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. alpha-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of alpha-tertiary and alpha-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-alpha-amido stannanes was transferred with up to 90% inversion of configuration at 100 degrees C.
• Kinetic Resolution of 2-Oxazolidinones via Catalytic, Enantioselective N-Acylation
  作者：Vladimir B. Birman、Hui Jiang、Ximin Li、Lei Guo、Eric W. Uffman

  DOI：10.1021/ja061560m

  日期：2006.5.1

  Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities.