ethyl (2R)-2-butyl-2-(2-naphthylmethyl)-3-oxobutanoate | 259800-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl (2R)-2-butyl-2-(2-naphthylmethyl)-3-oxobutanoate
• CAS: 259800-81-2
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: JEBVWNJCRLXTDX-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• 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-butyl-2-(2-naphthylmethyl)-3-oxobutanoate 在 sodium azide 、 甲烷磺酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以41%的产率得到ethyl (2S)-2-acetylamino-2-(2-naphthylmethyl)hexanoate
  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-butylacetoacetate 在 titanium(IV) tetraethanolate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 60.25h， 生成 ethyl (2R)-2-butyl-2-(2-naphthylmethyl)-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