1-(RS)-3-(RS)-α-(RS)-α-(2,4,6-Trimethylphenyl)-1,3-dioxo-1,3-dithiane-2-methanol | 139578-26-0

• 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: 1-(RS)-3-(RS)-α-(RS)-α-(2,4,6-Trimethylphenyl)-1,3-dioxo-1,3-dithiane-2-methanol
• CAS: 139578-26-0；139630-43-6
• 化学式: C₁₄H₂₀O₃S₂
• 分子量: 300.443
• InChiKey: RKHTVJTVGCUBCT-AGRHKRQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 、 trans-1(RS)-3(RS)-1,3-Dithiane 1,3-dioxide 在 吡啶 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以22%的产率得到1-(RS)-3-(RS)-α-(RS)-α-(2,4,6-Trimethylphenyl)-1,3-dioxo-1,3-dithiane-2-methanol
  参考文献：
  名称：

  Anion Reactions of 1,3-Dithiane 1,3-Dioxide with Carbonyl Compounds: High Diastereoselectivity with Aromatic Aldehydes under Conditions of Equilibrium Control

  摘要：

  We have investigated the anion chemistry of trans-1,3-dithiane 1,3-dioxide (4) with aldehydes and ketones, and we have found that this reagent undergoes highly selective addition reactions with aromatic aldehydes but only when reactions are under equilibrium control (achieved using Na anion of 4). Other metals invetsigated (Li, Mg, Al, Ce, Ti) gave either poorer selectivity or caused decomposition of 4. Zn-4 did give improved selectivity at low temperature but only with aromatic aldehydes. Reactions with ketones were limited to those without a-branching. A model that accounts for the high diastereoselectivity observed with aromatic aldehydes is presented.

  DOI：

  10.1021/jo00112a042

文献信息

• Highly stereoselective addition reactions of metallated trans-1,3-dithiane-1,3-dioxide to aldehydes
  作者：Varinder K. Aggarwal、Richard J. Franklin、Martin J. Rice

  DOI：10.1016/0040-4039(91)80580-y

  日期：1991.12

  The sodium anion of trans-1,3-dithiane-1,3-dioxide reacts with unhindered aromatic and heteroaromatic aldehydes to give adducts with 95:5 to 97:3 diastereoselectivity.