(-)-(2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-2-butenoate | 445009-18-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-(2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-2-butenoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methylbut-2-enoate
• CAS: 445009-18-7
• 化学式: C₂₈H₃₄F₃NO₃
• 分子量: 489.578
• InChiKey: BWUAPCKVOYYADX-LTFCNSMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-(2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-2-butenoate 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 (2R,3R)-3-(4-methoxyphenylamino)-4,4,4-trifluoro-2-methylbutan-1-ol
  参考文献：
  名称：

  New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids

  摘要：

  Racemic and chiral nonracemic alpha-substituted and alpha-unsubstituted beta-fluoroalkyl beta-amino acid derivatives 6 and 9 have been synthesized in two steps starting from fluorinated imidoyl chlorides 1 and ester enolates. This approach is based on the chemical reduction of previously obtained gamma-fluorinated beta-enamino esters 4 by using ZnI2/NaBH4 in a nonchelated aprotic medium (dry CH2Cl2) as the reducing agent. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction. The process takes place with high yields and with moderate to good diastereoselectivity. The best results related to diastereoselective reduction of chiral beta-enamino esters 4 were provided by the use of (-)-8-phenylmenthol as a chiral auxiliary.

  DOI：

  10.1021/jo025621k
• 作为产物：
  描述：

  8-苯基丙酸丙酯 、 N-(4-Methoxyphenyl)trifluoroacetimidoyl Chloride 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以85%的产率得到(-)-(2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-2-butenoate
  参考文献：
  名称：

  New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids

  摘要：

  Racemic and chiral nonracemic alpha-substituted and alpha-unsubstituted beta-fluoroalkyl beta-amino acid derivatives 6 and 9 have been synthesized in two steps starting from fluorinated imidoyl chlorides 1 and ester enolates. This approach is based on the chemical reduction of previously obtained gamma-fluorinated beta-enamino esters 4 by using ZnI2/NaBH4 in a nonchelated aprotic medium (dry CH2Cl2) as the reducing agent. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction. The process takes place with high yields and with moderate to good diastereoselectivity. The best results related to diastereoselective reduction of chiral beta-enamino esters 4 were provided by the use of (-)-8-phenylmenthol as a chiral auxiliary.

  DOI：

  10.1021/jo025621k

文献信息

• New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids
  作者：Santos Fustero、Belén Pina、Esther Salavert、Antonio Navarro、M. Carmen Ramírez de Arellano、Antonio Simón Fuentes

  DOI：10.1021/jo025621k

  日期：2002.7.1

  Racemic and chiral nonracemic alpha-substituted and alpha-unsubstituted beta-fluoroalkyl beta-amino acid derivatives 6 and 9 have been synthesized in two steps starting from fluorinated imidoyl chlorides 1 and ester enolates. This approach is based on the chemical reduction of previously obtained gamma-fluorinated beta-enamino esters 4 by using ZnI2/NaBH4 in a nonchelated aprotic medium (dry CH2Cl2) as the reducing agent. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction. The process takes place with high yields and with moderate to good diastereoselectivity. The best results related to diastereoselective reduction of chiral beta-enamino esters 4 were provided by the use of (-)-8-phenylmenthol as a chiral auxiliary.