1-(RS)-3-(RS)-α-(SR)-1,3-Dioxo-α-phenyl-1,3-dithiane-2-methanol | 128693-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 1-(RS)-3-(RS)-α-(SR)-1,3-Dioxo-α-phenyl-1,3-dithiane-2-methanol
• CAS: 128693-93-6；128778-16-5；139630-34-5；139630-38-9
• 化学式: C₁₁H₁₄O₃S₂
• 分子量: 258.362
• InChiKey: AONDSBPKGUYLQS-VFVAKGGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  trans-1(RS)-3(RS)-1,3-Dithiane 1,3-dioxide 、 苯甲醛 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以58%的产率得到1-(RS)-3-(RS)-α-(SR)-1,3-Dioxo-α-phenyl-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

• 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。
• 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.
• Aggarwal, Varinder K.; Davies, Ian W.; Franklin, Richard J., Journal of the Chemical Society. Perkin transactions I, 1991, # 3, p. 662 - 664
  作者：Aggarwal, Varinder K.、Davies, Ian W.、Franklin, Richard J.、Maddock, John、Mahon, Mary F.、Molloy, Kieran C.

  DOI：——

  日期：——