(S)-2-(isochroman-1-yl)-1-phenylethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(isochroman-1-yl)-1-phenylethan-1-one
• 英文别名: 2-[(1S)-3,4-dihydro-1H-isochromen-1-yl]-1-phenylethanone
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: ZARUVKLMGDVMCG-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 1-chloroisochroman 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-1-((R)-2-(4-fluorophenyl)-2-methylpyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)thiourea 作用下， 以 甲基叔丁基醚 为溶剂， 反应 24.0h， 以93%的产率得到(S)-2-(isochroman-1-yl)-1-phenylethan-1-one
  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.