(Rs,S)-N-(4,4,4-trifluoro-3-hydroxy-3-methyl-1-phenylbutylidene)-tert-butanesulfinamide

• 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: (Rs,S)-N-(4,4,4-trifluoro-3-hydroxy-3-methyl-1-phenylbutylidene)-tert-butanesulfinamide
• 英文别名: (NE,R)-2-methyl-N-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methyl-1-phenylbutylidene]propane-2-sulfinamide
• 化学式: C₁₅H₂₀F₃NO₂S
• 分子量: 335.391
• InChiKey: ORZKZIMAMQYJPL-ICAGZPENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Rs,S)-N-(4,4,4-trifluoro-3-hydroxy-3-methyl-1-phenylbutylidene)-tert-butanesulfinamide 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以84%的产率得到(S)-4,4,4-trifluoro-3-hydroxy-3-methyl-1-phenylbutan-1-one
  参考文献：
  名称：

  A practical diastereoselective synthesis of β-hydroxy-β-trifluoromethyl imines

  摘要：

  The asymmetric carbon-carbon bond formation reaction affording chiral (3-hydroxy-(3-trifluoromethyl imines is reported involving the nucleophilic addition of sulfinimine anions derived froth chiral N-(tert-butanesulfinyl) ketimines to trifluoromethyl ketones. The reaction tolerates a wide range of nucleophiles, giving the condensation products in good to excellent total yields with good diastereoselectivities (up to 85:15 dr). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.041
• 作为产物：
  描述：

  1,1,1-三氟丙酮 、 (R(S))-N-(1-phenylethylidene)-tert-butanesulfinamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 4.0h， 以83%的产率得到(Rs,S)-N-(4,4,4-trifluoro-3-hydroxy-3-methyl-1-phenylbutylidene)-tert-butanesulfinamide
  参考文献：
  名称：

  A practical diastereoselective synthesis of β-hydroxy-β-trifluoromethyl imines

  摘要：

  The asymmetric carbon-carbon bond formation reaction affording chiral (3-hydroxy-(3-trifluoromethyl imines is reported involving the nucleophilic addition of sulfinimine anions derived froth chiral N-(tert-butanesulfinyl) ketimines to trifluoromethyl ketones. The reaction tolerates a wide range of nucleophiles, giving the condensation products in good to excellent total yields with good diastereoselectivities (up to 85:15 dr). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.041

文献信息

• A practical diastereoselective synthesis of β-hydroxy-β-trifluoromethyl imines
  作者：Zhen-Jiang Liu、Ying-Qiao Mei、Jin-Tao Liu

  DOI：10.1016/j.tet.2006.11.041

  日期：2007.1

  The asymmetric carbon-carbon bond formation reaction affording chiral (3-hydroxy-(3-trifluoromethyl imines is reported involving the nucleophilic addition of sulfinimine anions derived froth chiral N-(tert-butanesulfinyl) ketimines to trifluoromethyl ketones. The reaction tolerates a wide range of nucleophiles, giving the condensation products in good to excellent total yields with good diastereoselectivities (up to 85:15 dr). (c) 2006 Elsevier Ltd. All rights reserved.