(2R,3R)-1,4-diiodobutane-2,3-diol | 190327-28-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R,3R)-1,4-diiodobutane-2,3-diol
• CAS: 190327-28-7
• 化学式: C₄H₈I₂O₂
• 分子量: 341.915
• InChiKey: MRDIDHLFTJNRDW-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对碘苯胺 、 (2R,3R)-1,4-diiodobutane-2,3-diol 在 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 216.0h， 以34%的产率得到(3S,4S)-1-(4-iodophenyl)pyrrolidine-3,4-diol
  参考文献：
  名称：

  Enantioselective Syntheses of trans-3,4-Difluoropyrrolidines and Investigation of Their Applications in Catalytic Asymmetric Synthesis

  摘要：

  Asymmetric Syntheses of enantiopure trans-3,4-difluoropyrrolidines have been prepared by the introduction of fluorine at both centers in a single operation; asymmetric epoxidations and additions to benzaldehyde were conducted using catalysts whose chirality depends on organofluorine asymmetry.

  DOI：

  10.1021/jo0513414
• 作为产物：
  描述：

  (+)-反式-4 5-双(碘甲基)-2,2-二甲基-1 3-二氧戊环 在 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 以96%的产率得到(2R,3R)-1,4-diiodobutane-2,3-diol
  参考文献：
  名称：

  Stereodependent Fusion and Fission of Vesicles:  Calcium Binding of Synthetic Gemini Phospholipids Containing Two Phosphate Groups

  摘要：

  Three different stereoisomers of a phosphatidic acid analog bearing two phosphate groups have been synthesized from tartaric acid and erythritol. The obtained diastereomeric gemini surfactants differ in their aggregation behavior due to the different spatial orientations of their functional groups. The most remarkable difference in aggregation behavior is encountered when calcium ions are added to vesicle suspensions of the respective isomers. The vesicles formed from the (S,S) and (R,R) isomer undergo fusion, whereas those of the (R,S) isomer show vesicle fission. This remarkable behavior can be explained by a change in the molecular packing of the lipid molecules upon the complexation with calcium ions. An analysis of physical data obtained prior to and after the addition of the calcium ions reveals that the head groups of the diastereomeric surfactants respond differently to these ions: those of the (S,S) isomer increase in size, whereas those of the (R,S) isomer decrease in size. This phenomenon accounts for occurrence of fusion and fission of the vesicles, respectively.

  DOI：

  10.1021/ja962303s