(3R,αS)-tert-Butyl 3-(N-α-methylbenzylamino)-3-phenylpropanoate | 146937-36-2

• 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: (3R,αS)-tert-Butyl 3-(N-α-methylbenzylamino)-3-phenylpropanoate
• 英文别名: tert-butyl (3R,αS)-3-[N-(α-methylbenzyl)amino]-3-phenylpropanoate；tert-butyl (3R)-3-phenyl-3-[[(1S)-1-phenylethyl]amino]propanoate
• CAS: 146937-36-2
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: XSGZMPZHCHKKDP-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,αS)-tert-Butyl 3-(N-α-methylbenzylamino)-3-phenylpropanoate 在 氯化亚砜 、 甲基溴化镁 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 (4R,αS)-N(1)-(α-methylbenzyl)-4-phenylazetidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives

  摘要：

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.008
• 作为产物：
  描述：

  tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-phenylpropanoate 在 ammonium cerium(IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以86%的产率得到(3R,αS)-tert-Butyl 3-(N-α-methylbenzylamino)-3-phenylpropanoate
  参考文献：
  名称：

  Chemoselective oxidative debenzylation of tertiary N-benzyl amines

  摘要：

  含有一种或多种叔胺的处理 用硝酸高铈铵水溶液保护 N-苄基 导致干净的 N-脱苄基反应以提供相应的 仲胺。

  DOI：

  10.1039/b000071j

文献信息

• Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate
  作者：Steven D. Bull、Stephen G. Davies、Garry Fenton、Andrew W. Mulvaney、R. Shyam Prasad、Andrew D. Smith

  DOI：10.1039/b006852g

  日期：——

  Treatment of a range of N-benzyl tertiary amines with aqueous ceric ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-N-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and S-benzyl ethers.

  将一系列N-苄基三级胺与水合铈铵硝酸盐反应，结果发生N-去苄基化，得到相应的二级胺。在N-苄基酰胺、O-苄基醚、O-苄基酯、O-苄基酚酸盐和S-苄基醚存在的情况下，显示出N-苄基三级胺的化学选择性单N-去苄基化反应的发生。
• Lithium (α-methylbenzyl)allylamide: a differentially protected chiral ammonia equivalent for the asymmetric synthesis of β-amino acids and β-lactams
  作者：Stephen G. Davies、David R. Fenwick

  DOI：10.1039/c39950001109

  日期：——

  The addition products from the highly stereoselective conjugate additions of lithium (αS)-(α-methylbenzyl)allylamide to α, β-unsaturated tert-butyl esters are efficiently deallylated with tris(triphenylphosphine)rhodium(I) chloride and converted, after transesterification to the methyl esters and cyclisation with methylmagnesium bromide, to the corresponding homochiral N-(α-methylbenzyl)-4-substituted-azetidm-2-ones

  由（αS）-（α-甲基苄基）烯丙基酰胺高度立体选择性共轭加成至α，β-不饱和叔丁酯的加成产物可有效地与三（三苯基膦）铑（I）氯化物脱酯并在酯交换反应后转化生成甲基酯，并用甲基溴化镁环化，生成相应的手性N-（α-甲基苄基）-4-取代的氮杂环丁烷-2-酮。
• Synthesis of<i>β</i>-Amino Esters by the Conjugate Addition of Nitrogen Nucleophiles to<i>α</i>,<i>β</i>-Unsaturated Esters Having Chiral<i>p</i>-Tolylsulfinyl Groups
  作者：Haruo Matsuyama、Nobuhiro Itoh、Masato Yoshida、Nobumasa Kamigata、Sigeru Sasaki、Masahiko Iyoda

  DOI：10.1246/cl.1997.375

  日期：1997.4

  The conjugate addition of nitrogen nucleophiles to t-butyl (E)-2-(p-tolylsulfinyl)cinnamates (1) afforded the corresponding chiral β-amino esters, which are important building blocks for synthesis of biologically active polyamine alkaloids. The diastereoselectivity of the reactions was 49 to 89%, and (S)-β-amino esters were obtained from (R)-1 while (R)-β-amino esters were synthesized from (S)-1, respectively

  氮亲核试剂与叔丁基 (E)-2-(对甲苯基亚磺酰基) 肉桂酸酯 (1) 的共轭加成得到相应的手性 β-氨基酯，这是合成生物活性多胺生物碱的重要组成部分。反应的非对映选择性为49%至89%，(S)-β-氨基酯由(R)-1合成，(R)-β-氨基酯由(S)-1合成。
• A New Chiral BLA Promoter for Asymmetric Aza Diels-Alder and Aldol-Type Reactions of Imines
  作者：Kazuaki Ishihara、Mayumi Miyata、Kouji Hattori、Toshiji Tada、Hisashi Yamamoto

  DOI：10.1021/ja00102a019

  日期：1994.11

  A new type of chiral promoter for double asymmetric inductions of aza Diels-Alder and aldol-type reactions of imines is prepared from trialkyl berates (B(OMe)(3) or B(OPh)(3)) and optically pure binaphthol; X-ray analysis of the boron complex demonstrates that it exists as a Bronsted acid-assisted chiral Lewis acid(BLA). The aldol-type reactions of a number of N-benzhydrylimines derived from aromatic aldehydes with the ketene silyl acetal derived from tert-butyl acetate mediated by the chiral BLA afford beta-amino acid esters with high enantioselectivity. The solution conformations of the BLA.imine complexes have been studied using H-1 NMR analysis and difference NOE measurements. The absolute configurations of the adducts can be understood in terms of a rational model involving an intramolecular hydrogen binding interaction via a Bronsted acid.
• Hattori, Kouji; Miyata, Mayumi; Yamamoto, Hisashi, Journal of the American Chemical Society, 1993, vol. 115, # 3, p. 1151 - 1152
  作者：Hattori, Kouji、Miyata, Mayumi、Yamamoto, Hisashi

  DOI：——

  日期：——