(2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl (2S,3S)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-butanoate | 445009-40-5

• 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: (2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl (2S,3S)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-butanoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (2S,3S)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methylbutanoate
• CAS: 445009-40-5
• 化学式: C₂₈H₃₆F₃NO₃
• 分子量: 491.594
• InChiKey: BEUZFBVDQYFFDN-XZPPUWBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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 (2S,3S)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-butanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R*,3R*)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methylbutan-1-ol
  参考文献：
  名称：

  通过脯氨酸催化的交叉曼尼希反应对氟代γ-氨基醇进行高度对映选择性合成。

  摘要：

  描述了仅两个步骤就以光学纯净形式合成氟化β-烷基γ-氨基醇的新的简单路线，其特征在于从廉价且容易获得的起始原料进行脯氨酸催化。所应用的策略允许将多样性引入到这些化合物的β-氟代烷基和α-烷基中。[反应：看文字]

  DOI：

  10.1021/ol050791f
• 作为产物：
  描述：

  N-(4-Methoxyphenyl)trifluoroacetimidoyl Chloride 在 sodium tetrahydroborate 、 zinc(II) iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 37.5h， 生成 (2S,5S,1R)-5-methyl-2-(1-methyl-1-phenylethyl)-cyclohexyl (2S,3S)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-butanoate
  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.
• Highly Enantioselective Synthesis of Fluorinated γ-Amino Alcohols through Proline-Catalyzed Cross-Mannich Reaction
  作者：Santos Fustero、Diego Jiménez、Juan F. Sanz-Cervera、María Sánchez-Roselló、Elisabet Esteban、Antonio Simón-Fuentes

  DOI：10.1021/ol050791f

  日期：2005.8.1

  A new, simple route for the synthesis of fluorinated beta-alkyl gamma-amino alcohols in optically pure form in only two steps and featuring proline catalysis from inexpensive and readily available starting materials is described. The applied strategy allows for the introduction of diversity into both the beta-fluoroalkyl and alpha-alkyl groups of these compounds. [reaction: see text]

  描述了仅两个步骤就以光学纯净形式合成氟化β-烷基γ-氨基醇的新的简单路线，其特征在于从廉价且容易获得的起始原料进行脯氨酸催化。所应用的策略允许将多样性引入到这些化合物的β-氟代烷基和α-烷基中。[反应：看文字]