(2R,4R)-2-Allyl-5-methyl-4-(2,2,2-trifluoro-acetylamino)-hexanoic acid methyl ester | 186903-49-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,4R)-2-Allyl-5-methyl-4-(2,2,2-trifluoro-acetylamino)-hexanoic acid methyl ester
• 英文别名: methyl (2R,4R)-5-methyl-2-prop-2-enyl-4-[(2,2,2-trifluoroacetyl)amino]hexanoate
• CAS: 186903-49-1
• 化学式: C₁₃H₂₀F₃NO₃
• 分子量: 295.302
• InChiKey: VILWDNCUUIFLNO-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-Allyl-5-methyl-4-(2,2,2-trifluoro-acetylamino)-hexanoic acid methyl ester 在 水 作用下， 生成 (3R,5R)-3-Allyl-5-isopropyl-pyrrolidin-2-one
  参考文献：
  名称：

  1,3-Asymmetric induction in enolate alkylation reactions of N-protected γ-amino acid derivatives

  摘要：

  Dianions derived from N-TFA and N-Boc gamma-amino acid esters and amides undergo highly stereoselective alpha-alkylation reactions The roles of HMPA, of the cation, the electrophile, and of steric factors were studied. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02263-0
• 作为产物：
  描述：

  (4R)-tert-butoxycarbonylamino-5-methyl-hexanoic acid methyl ester 在 六甲基磷酰三胺 、 三乙胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 反应 2.08h， 生成 (2R,4R)-2-Allyl-5-methyl-4-(2,2,2-trifluoro-acetylamino)-hexanoic acid methyl ester
  参考文献：
  名称：

  1,3-Asymmetric induction in enolate alkylation reactions of N-protected γ-amino acid derivatives

  摘要：

  Dianions derived from N-TFA and N-Boc gamma-amino acid esters and amides undergo highly stereoselective alpha-alkylation reactions The roles of HMPA, of the cation, the electrophile, and of steric factors were studied. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02263-0

文献信息

• Synthesis of γ-Amino Esters via Mn-Mediated Radical Addition to Chiral γ-Hydrazonoesters
  作者：Gregory K. Friestad、Koushik Banerjee

  DOI：10.1021/ol802932v

  日期：2009.3.5

  Highly stereoselective Mn-mediated couplings of alkyl iodides with chiral N-acylhydrazones bearing ester functionality afford a series of gamma-hydrazino esters, including gamma-substituted, alpha,gamma-disubstituted, and alpha,alpha,gamma-trisubstituted examples. In contrast to prior work with chiral N-acylhydrazones, high stereoselectivity was observed even in the absence of Lewis acid. Microwave-assisted acylation with trifluoroacetic anhydride and reductive N-N bond cleavage provided the gamma-amino ester functionality in a synthetically useful N-TFA-protected form.