ethyl (2R)-2-(4-bromobenzyl)-2-methyl-3-oxobutanoate | 259800-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (2R)-2-(4-bromobenzyl)-2-methyl-3-oxobutanoate
• 英文别名: ethyl (2R)-2-[(4-bromophenyl)methyl]-2-methyl-3-oxobutanoate
• CAS: 259800-78-7
• 化学式: C₁₄H₁₇BrO₃
• 分子量: 313.191
• InChiKey: WFNGRSOWPJCCMF-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (2R)-2-(4-bromobenzyl)-2-methyl-3-oxobutanoate 在 盐酸 、 sodium azide 、 甲烷磺酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 48.0h， 生成 (S)-α-(4-bromobenzyl)alanine hydrochloride
  参考文献：
  名称：

  Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary

  摘要：

  We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00457-7
• 作为产物：
  描述：

  2,3-O-isopropylidene-γ-D-ribonolactone 2-methylacetoacetate 在 titanium(IV) tetraethanolate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.25h， 生成 ethyl (2R)-2-(4-bromobenzyl)-2-methyl-3-oxobutanoate
  参考文献：
  名称：

  Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary

  摘要：

  We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00457-7

文献信息

• Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary
  作者：Marcial Moreno-Mañas、Elisenda Trepat、Rosa M. Sebastián、Adelina Vallribera

  DOI：10.1016/s0957-4166(99)00457-7

  日期：1999.10

  We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.