(S)-1-Phenyl-3-[(2,4,6-triisopropylphenyl)sulfinyl]propan-1-one | 312310-73-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-Phenyl-3-[(2,4,6-triisopropylphenyl)sulfinyl]propan-1-one
• 英文别名: 1-phenyl-3-[(S)-[2,4,6-tri(propan-2-yl)phenyl]sulfinyl]propan-1-one
• CAS: 312310-73-9
• 化学式: C₂₄H₃₂O₂S
• 分子量: 384.583
• InChiKey: LXPSGHARMKNWTQ-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-Phenyl-3-[(2,4,6-triisopropylphenyl)sulfinyl]propan-1-one 在 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-1-Phenyl-3-(2,4,6-triisopropyl-benzenesulfonyl)-propan-1-ol
  参考文献：
  名称：

  1,4-Asymmetric reduction of γ-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group

  摘要：

  Reduction of gamma-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group with DIBAL gives gamma-hydroxy sulfoxides with high stereoselectivity in the ratio 95:5. In comparison with the lower stereoselectivities obtained in the reaction of gamma-keto sulfoxides bearing p-tolyl or 2,4,6-trimethylphenyl groups, the sterically bulky (2,4,6-triisopropylphenyl)sulfinyl group is extremely efficient in effecting high 1,4-remote asymmetric induction.

  DOI：

  10.1039/b004782l
• 作为产物：
  描述：

  (S_S,SR)-1-Phenyl-3-[(2,4,6-triisopropylphenyl)sulfinyl]propan-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以66%的产率得到(S)-1-Phenyl-3-[(2,4,6-triisopropylphenyl)sulfinyl]propan-1-one
  参考文献：
  名称：

  1,4-Asymmetric reduction of γ-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group

  摘要：

  Reduction of gamma-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group with DIBAL gives gamma-hydroxy sulfoxides with high stereoselectivity in the ratio 95:5. In comparison with the lower stereoselectivities obtained in the reaction of gamma-keto sulfoxides bearing p-tolyl or 2,4,6-trimethylphenyl groups, the sterically bulky (2,4,6-triisopropylphenyl)sulfinyl group is extremely efficient in effecting high 1,4-remote asymmetric induction.

  DOI：

  10.1039/b004782l

文献信息

• 1,4-Asymmetric reduction of γ-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group
  作者：Shuichi Nakamura、Masayuki Kuroyanagi、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1039/b004782l

  日期：——

  Reduction of gamma-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group with DIBAL gives gamma-hydroxy sulfoxides with high stereoselectivity in the ratio 95:5. In comparison with the lower stereoselectivities obtained in the reaction of gamma-keto sulfoxides bearing p-tolyl or 2,4,6-trimethylphenyl groups, the sterically bulky (2,4,6-triisopropylphenyl)sulfinyl group is extremely efficient in effecting high 1,4-remote asymmetric induction.