(R)-1-(4-mesityl-2-thioxooxazolidin-3-yl)ethanone | 924265-82-7

• 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)-1-(4-mesityl-2-thioxooxazolidin-3-yl)ethanone
• 英文别名: 1-[(4R)-2-sulfanylidene-4-(2,4,6-trimethylphenyl)-1,3-oxazolidin-3-yl]ethanone
• CAS: 924265-82-7
• 化学式: C₁₄H₁₇NO₂S
• 分子量: 263.36
• InChiKey: MCIRHUFPKRXBSC-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(4-mesityl-2-thioxooxazolidin-3-yl)ethanone 、 正丁醛 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R)-3-hydroxy-1-((R)-4-mesityl-2-thioxooxazolidin-3-yl)hexan-1-one 、 (S)-3-hydroxy-1-((R)-4-mesityl-2-thioxooxazolidin-3-yl)hexan-1-one
  参考文献：
  名称：

  Highly Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries

  摘要：

  Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and alpha,beta-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).

  DOI：

  10.1021/ol062688b
• 作为产物：
  描述：

  (R)-N-((R)-1-mesityl-2-(4-methoxybenzyloxy)ethyl)-2-methylpropane-2-sulfinamide 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (R)-1-(4-mesityl-2-thioxooxazolidin-3-yl)ethanone
  参考文献：
  名称：

  Highly Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries

  摘要：

  Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and alpha,beta-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).

  DOI：

  10.1021/ol062688b

文献信息

• Highly Selective Acetate Aldol Additions Using Mesityl-Substituted Chiral Auxiliaries
  作者：Michael T. Crimmins、Mariam Shamszad

  DOI：10.1021/ol062688b

  日期：2007.1.1

  Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and alpha,beta-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).