3-(2-methyl-1,3-dithian-2-yl)-propanal

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 3-(2-methyl-1,3-dithian-2-yl)-propanal
• 英文别名: 3-(2-methyl-[1,3]dithian-2-yl)-propionaldehyde；3-(2-Methyl-1,3-dithian-2-yl)propanal；3-(2-methyl-1,3-dithian-2-yl)propanal
• 化学式: C₈H₁₄OS₂
• 分子量: 190.331
• InChiKey: WKCVOXPUFXWQIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-methyl-1,3-dithian-2-yl)-propanal 在 copper(l) cyanide 、 lithium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 43.25h， 生成 4-(triphenylsilanyl)-3-[3-(2-methyl-[1,3]dithian-2-yl)-propylidene]dihydrofuran-2-one
  参考文献：
  名称：

  SmI₂-Mediated Radical Cyclizations Directed by a C−Si Bond

  摘要：

  The use of a silicon stereocontrol element in cyclobutanol and cyclopentanol-forming cyclizations mediated by SmI2 results in excellent diastereocontrol. The C-Si bond in the products of cyclization provides a versatile handle for further manipulation. An asymmetric route to cyclization substrates involving copper-catalyzed silyl transfer has also been developed.

  DOI：

  10.1021/ol102278c
• 作为产物：
  描述：

  在 盐酸 作用下， 以95%的产率得到3-(2-methyl-1,3-dithian-2-yl)-propanal
  参考文献：
  名称：

  Catalytic enantioselective addition of diethylzinc to 1,3-dithian-2-yl substituted aliphatic aldehydes: a new approach to optically active 2-(hydroxyalkyl)-1,3-dithianes

  摘要：

  Asymmetric synthesis of 2-(hydroxyalkyl)-1,3-dithianes was achieved in good yields of up to 81% by using various 1,3-dithian-2-yl-substituted aliphatic aldehydes as substrates in the catalytic enantioselective addition of diethylzinc, With fair enantiomeric ratios of up to 85:15 in the enantiocontrolled ethylation step this synthetic approach provides an entry towards potential chiral building blocks. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00029-x

文献信息

• 一种番茄红素中间体的制备方法
  申请人：厦门大学

  公开号：CN106349002B

  公开（公告）日：2019-04-19

  一种番茄红素中间体的制备方法，涉及番茄红素。1)将化合物6溶解在醚类溶剂中，加入对甲苯磺酰肼溶液，再加入化合物7，反应后加入饱和氯化铵淬灭，得化合物8；2)将化合物8溶于乙腈/水溶剂中，加入对甲苯磺酸吡啶盐，反应后用饱和碳酸氢钠溶液淬灭，得粗产物；粗产物溶于苯类溶剂，有机碱以及相同的对甲苯磺酰氯，反应物经饱和氯化铵溶液淬灭、萃取、浓缩、纯化后得化合物9；3)化合物9溶于醚类溶剂中，加入丁基锂试剂，加入单质碘溶液，反应后，经饱和氯化铵溶液淬灭、萃取、浓缩、纯化后得到番茄红素中间体(3E，5E，7E)‑8‑碘‑4‑甲基‑1,3,5,7‑壬四烯。
• SmI₂-Mediated Radical Cyclizations Directed by a C−Si Bond
  作者：Hassan Y. Harb、Karl D. Collins、Jose V. Garcia Altur、Sue Bowker、Leonie Campbell、David J. Procter

  DOI：10.1021/ol102278c

  日期：2010.12.3

  The use of a silicon stereocontrol element in cyclobutanol and cyclopentanol-forming cyclizations mediated by SmI2 results in excellent diastereocontrol. The C-Si bond in the products of cyclization provides a versatile handle for further manipulation. An asymmetric route to cyclization substrates involving copper-catalyzed silyl transfer has also been developed.
• Catalytic enantioselective addition of diethylzinc to 1,3-dithian-2-yl substituted aliphatic aldehydes: a new approach to optically active 2-(hydroxyalkyl)-1,3-dithianes
  作者：Jörg Wilken、Martin Winter、Ingfried Stahl、Jürgen Martens

  DOI：10.1016/s0957-4166(00)00029-x

  日期：2000.3

  Asymmetric synthesis of 2-(hydroxyalkyl)-1,3-dithianes was achieved in good yields of up to 81% by using various 1,3-dithian-2-yl-substituted aliphatic aldehydes as substrates in the catalytic enantioselective addition of diethylzinc, With fair enantiomeric ratios of up to 85:15 in the enantiocontrolled ethylation step this synthetic approach provides an entry towards potential chiral building blocks. (C) 2000 Elsevier Science Ltd. All rights reserved.