trans-3,5-dimethyl-1,2-dithiolane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: trans-3,5-dimethyl-1,2-dithiolane
• 英文别名: 3,5-dimethyl-[1,2]-dithiolane；(3S,5S)-3,5-dimethyldithiolane
• 化学式: C₅H₁₀S₂
• 分子量: 134.266
• InChiKey: KFUVOYOTMWUCHL-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,4R)-2,4-pentanediol ditosylate 在 sodium sulfide 、 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 trans-3,5-dimethyl-1,2-dithiolane
  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

• Graaf, Wim de; Damste, Jaap S. Sinninghe; Leeuw, Jan W. de, Journal of the Chemical Society. Perkin transactions I, 1995, # 6, p. 635 - 640
  作者：Graaf, Wim de、Damste, Jaap S. Sinninghe、Leeuw, Jan W. de

  DOI：——

  日期：——
• Caserio, Majorie C.; Kim, Jhong J., Phosphorus and Sulfur and the Related Elements, 1985, vol. 23, p. 169 - 196
  作者：Caserio, Majorie C.、Kim, Jhong J.

  DOI：——

  日期：——
• Conformation, configuration, and reactivity of thiosulfonium ions derived from 1,2-dithianes and 1,2-dithiolanes. Stereoelectronic effects
  作者：Marjorie C. Caserio、Jhong K. Kim、Scott D. Kahn、Warren J. Hehre

  DOI：10.1021/ja00295a044

  日期：1985.5