苏-(2R,4R)-戊二硫醇 | 4038-08-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 中文名称: 苏-(2R,4R)-戊二硫醇
• 英文名称: (+/-)-2,4-pentanedithiol
• 英文别名: rac.-Pentandithiol-(2.4)；racem. pentane-2,4-dithiol；(2S,4S)-pentane-2,4-dithiol
• CAS: 4038-08-8；5953-46-8；5954-76-7；84799-98-4
• 化学式: C₅H₁₂S₂
• 分子量: 136.282
• InChiKey: WUVMJSSTEMBGRQ-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苏-(2R,4R)-戊二硫醇 在 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 21.5h， 生成 N-[(1S)-1-benzyl-2-hydroxyethyl]-2,4,6-trimethyl-1,3-dithiane-2-carboxamide
  参考文献：
  名称：

  Chiral oxazoline-1,3-dithianes: new effective nitrogen–sulfur donating ligands in asymmetric catalysis

  摘要：

  A series of new chiral oxazoline-1,3-dithianes has been easily synthesized and used as ligands for asymmetric catalysis. The conjugate addition of Et2Zn to enones resulted in ees of up to 69%, whereas the Pd-catalyzed allylic alkylation led to the expected products in almost quantitative yields and up to 90% enantioselectivity. The ligand's conformation has been explored using a combination of X-ray and NMR measurements, indicating the presence of a remarkable anomeric effect, which accounts for the preference of the oxazoline ring for the axial location. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.043
• 作为产物：
  描述：

  trans-3,5-dimethyl-1,2-dithiolane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 苏-(2R,4R)-戊二硫醇
  参考文献：
  名称：

  Chiral oxazoline-1,3-dithianes: new effective nitrogen–sulfur donating ligands in asymmetric catalysis

  摘要：

  A series of new chiral oxazoline-1,3-dithianes has been easily synthesized and used as ligands for asymmetric catalysis. The conjugate addition of Et2Zn to enones resulted in ees of up to 69%, whereas the Pd-catalyzed allylic alkylation led to the expected products in almost quantitative yields and up to 90% enantioselectivity. The ligand's conformation has been explored using a combination of X-ray and NMR measurements, indicating the presence of a remarkable anomeric effect, which accounts for the preference of the oxazoline ring for the axial location. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.043

文献信息

• Conformational analysis. XVIII. 1,3-Dithianes. Conformational preferences of alkyl substituents and the chair-boat energy difference
  作者：Ernest L. Eliel、Robert O. Hutchins

  DOI：10.1021/ja01038a050

  日期：1969.5
• Tavernier, D.; Hosten, N.; Anteunis, M. J. O., Bulletin des Societes Chimiques Belges, 1982, vol. 91, # 10, p. 845 - 864
  作者：Tavernier, D.、Hosten, N.、Anteunis, M. J. O.、Spiessens, L. I.、Becu, C.、Ketelaere, Antenius-de

  DOI：——

  日期：——
• Carbon-13 nuclear magnetic resonance spectra of saturated heterocycles. 3. 1,3-Dithianes
  作者：Ernest L. Eliel、V. S. Rao、Frank G. Riddell

  DOI：10.1021/ja00428a032

  日期：1976.6