(1R,3R)-2-(2,2-Dimethyl-propylidene)-[1,3]dithiane 1,3-dioxide | 128693-97-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (1R,3R)-2-(2,2-Dimethyl-propylidene)-[1,3]dithiane 1,3-dioxide
• 英文别名: (1R,3R)-2-(2,2-dimethylpropylidene)-1,3-dithiane 1,3-dioxide
• CAS: 128693-97-0
• 化学式: C₉H₁₆O₂S₂
• 分子量: 220.357
• InChiKey: VKWGIACVUAXGHB-CHWSQXEVSA-N

物化性质

• 沸点：
  475.2±45.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  trans-1(RS)-3(RS)-1,3-Dithiane 1,3-dioxide 、 特戊醛 以31%的产率得到
  参考文献：
  名称：

  AGGARWAL, VARINDER K.;DAVIES, IAN W.;MADDOCK, JOHN;MAHON, MARY F.;MOLLOY,+, TETRAHEDRON LETT., 31,(1990) N, C. 135-138

  摘要：

  DOI：

文献信息

• Additions of aldehydes to metallated trans-1,3-Dithiane-S,S-dioxide under conditions of kinetic and thermodynamic control
  作者：Varinder K Aggarwal、Ian W Davies、John Maddock、Mary F Mahon、Kieran C Molloy

  DOI：10.1016/s0040-4039(00)94354-5

  日期：1990.1

  The chiral acyl anion equivalent (1) can be metallated with n-BuLi/py and reacts with aldehydes to give adducts in high yield. At −78δC the reaction is under kinetic control whereas at 0δC equilibration occurs with PhCHO and t-BuCHO resulting in good yields of single diastereoisomers.

  手性酰基阴离子当量（1）可以用n-BuLi / py进行金属化，并与醛反应以高收率得到加合物。在-78δC时，反应处于动力学控制之下，而在0δC时，PhCHO和t-BuCHO发生平衡，从而导致单一非对映异构体的收率很高。
• Anion Reactions of 1,3-Dithiane 1,3-Dioxide with Carbonyl Compounds: High Diastereoselectivity with Aromatic Aldehydes under Conditions of Equilibrium Control
  作者：Varinder K. Aggarwal、Richard Franklin、John Maddock、Graham R. Evans、Abraham Thomas、Mary F. Mahon、Kieran C. Molloy、Martin J. Rice

  DOI：10.1021/jo00112a042

  日期：1995.4

  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.