(R)-3-((1-(4-fluorophenyl)ethyl)amino)propan-1-ol

• 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: (R)-3-((1-(4-fluorophenyl)ethyl)amino)propan-1-ol
• 英文别名: 3-[[(1R)-1-(4-fluorophenyl)ethyl]amino]propan-1-ol
• 化学式: C₁₁H₁₆FNO
• 分子量: 197.253
• InChiKey: RHNGOFVOYCWDHU-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-((1-(4-fluorophenyl)ethyl)amino)propan-1-ol 在 盐酸 、 4-二甲氨基吡啶 、 四甲基乙二胺 、 仲丁基锂 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 73.75h， 生成 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-1-((R)-2-(4-fluorophenyl)-2-methylpyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)urea
  参考文献：
  名称：

  Conformational Control of Chiral Amido-Thiourea Catalysts Enables Improved Activity and Enantioselectivity

  摘要：

  While aryl pyrrolidinoamido-thioureas derived from alpha-amino acids are effective catalysts in a number of asymmetric transformations, they exist as mixtures of slowly interconverting amide rotamers. Herein, the compromising role of amide bond isomerism is analyzed experimentally and computationally. A modified catalyst structure that exists almost exclusively as a single amide rotamer is introduced. This modification is shown to result in improved reactivity and enantioselectivity by minimizing competing reaction pathways.

  DOI：

  10.1021/acs.orglett.6b01435
• 作为产物：
  描述：

  3-氯-1-丙醇 、 (R)-1-(4-氟苯基)乙胺 以 水 为溶剂， 反应 16.0h， 以70%的产率得到(R)-3-((1-(4-fluorophenyl)ethyl)amino)propan-1-ol
  参考文献：
  名称：

  Conformational Control of Chiral Amido-Thiourea Catalysts Enables Improved Activity and Enantioselectivity

  摘要：

  While aryl pyrrolidinoamido-thioureas derived from alpha-amino acids are effective catalysts in a number of asymmetric transformations, they exist as mixtures of slowly interconverting amide rotamers. Herein, the compromising role of amide bond isomerism is analyzed experimentally and computationally. A modified catalyst structure that exists almost exclusively as a single amide rotamer is introduced. This modification is shown to result in improved reactivity and enantioselectivity by minimizing competing reaction pathways.

  DOI：

  10.1021/acs.orglett.6b01435

文献信息

• Conformational Control of Chiral Amido-Thiourea Catalysts Enables Improved Activity and Enantioselectivity
  作者：Dan Lehnherr、David D. Ford、Andrew J. Bendelsmith、C. Rose Kennedy、Eric N. Jacobsen

  DOI：10.1021/acs.orglett.6b01435

  日期：2016.7.1

  While aryl pyrrolidinoamido-thioureas derived from alpha-amino acids are effective catalysts in a number of asymmetric transformations, they exist as mixtures of slowly interconverting amide rotamers. Herein, the compromising role of amide bond isomerism is analyzed experimentally and computationally. A modified catalyst structure that exists almost exclusively as a single amide rotamer is introduced. This modification is shown to result in improved reactivity and enantioselectivity by minimizing competing reaction pathways.