(2R*,2'R*,2''S*,2'''S*)-octahydro[2,2':2'(3'H),2'':2''(3''H),2'''-quaterfuran]-2,2'''(3H,3'''H)-dicarboxaldehyde | 289887-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R*,2'R*,2''S*,2'''S*)-octahydro[2,2':2'(3'H),2'':2''(3''H),2'''-quaterfuran]-2,2'''(3H,3'''H)-dicarboxaldehyde
• 英文别名: (2R)-2-[(2R)-2-[(2S)-2-[(2S)-2-formyloxolan-2-yl]oxolan-2-yl]oxolan-2-yl]oxolane-2-carbaldehyde
• CAS: 289887-89-4
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: VDJZENSQURQJSF-USTZCAOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R*,2'R*,2''S*,2'''S*)-octahydro[2,2':2'(3'H),2'':2''(3''H),2'''-quaterfuran]-2,2'''(3H,3'''H)-dicarboxaldehyde 在 烯丙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以65%的产率得到(5R*,6R*,11R*,16R*)-1,7,12,17,22-pentaoxatetraspiro[4.0.4.0.4.0.4.3]tricosan-21-one
  参考文献：
  名称：

  Vicinal Tetrahydrofuranyl Substitution of Alkyl Chains. Tetra-, Penta-, and Hexafunctionalized Arrays

  摘要：

  The tetrakis (tetrahydrofuranyl) dialdehydes 14 and 19 are accessible by oxidative cleavage of extensively substituted cyclohexenes, which have in turn been assembled in a stereocontrolled manner. Reaction of 14 with an excess of the Normant reagent followed by ring closure resulted in conversion to the hexafunctionalized polyether 15. Allylindation of the same dialdehyde gave rise to lactol 16, a reactivity pattern that was essentially duplicated when 19 was treated with the Normant reagent. Attempts to add allylmagnesium bromide to 19 resulted in operation of a Tishchenko reaction viith formation of lactone 23. By means of X-ray diffraction analysis, it was possible to ascertain the conformation adopted by 20 and 23 in the solid state. In addition, 15 was shown to populate a conformation in which the oxygen are very predominantly in gauche arrangements, this structural preorganization taking place in the absence of any metal ions.

  DOI：

  10.1021/jo0001075
• 作为产物：
  描述：

  在 吡啶 、 lead(IV) acetate 、 四氧化锇 、 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 作用下， 以 甲醇 、 苯 为溶剂， 反应 5.5h， 生成 (2R*,2'R*,2''S*,2'''S*)-octahydro[2,2':2'(3'H),2'':2''(3''H),2'''-quaterfuran]-2,2'''(3H,3'''H)-dicarboxaldehyde
  参考文献：
  名称：

  Vicinal Tetrahydrofuranyl Substitution of Alkyl Chains. Tetra-, Penta-, and Hexafunctionalized Arrays

  摘要：

  The tetrakis (tetrahydrofuranyl) dialdehydes 14 and 19 are accessible by oxidative cleavage of extensively substituted cyclohexenes, which have in turn been assembled in a stereocontrolled manner. Reaction of 14 with an excess of the Normant reagent followed by ring closure resulted in conversion to the hexafunctionalized polyether 15. Allylindation of the same dialdehyde gave rise to lactol 16, a reactivity pattern that was essentially duplicated when 19 was treated with the Normant reagent. Attempts to add allylmagnesium bromide to 19 resulted in operation of a Tishchenko reaction viith formation of lactone 23. By means of X-ray diffraction analysis, it was possible to ascertain the conformation adopted by 20 and 23 in the solid state. In addition, 15 was shown to populate a conformation in which the oxygen are very predominantly in gauche arrangements, this structural preorganization taking place in the absence of any metal ions.

  DOI：

  10.1021/jo0001075

文献信息

• X-ray Crystallographic and Mass Spectrometric Probing of the Conformational and Ionophoric Properties of Stereoisomeric Hexatetrahydrofuranylhexane Segments
  作者：David G. Hilmey、Barry D. Davis、Judith C. Gallucci、Jennifer S. Brodbelt、Leo A. Paquette

  DOI：10.1021/jo7016229

  日期：2007.11.1

  [Graphics]A full account of the synthesis of the 12 hexacyclic tetrahydrofuran isomers represented by the nearby formulas is first provided. The key steps involved in further elaboration of the spiro ethers 12, 15, 28, and 45 include controlled ozonolysis, 1,2-addition of the Normant reagent, and heterocyclization. Eight of the end products proved to be sufficiently crystalline to enable X-ray analysis and determination of their solid-state conformational features. The alkali metal ion selectivities of the 12 hexamers were evaluated by a picrate extraction method and by electrospray ionization mass spectrometry (ESI-MS) which indicated that small, but significant, selectivity differences exist within the groups of diastereomers. These results revealed that each hexamer demonstrated a preference for lithium ion complexation relative to sodium or potassium ion complexation. Stereoisomeric classification of the hexamers was based on the competition between two dissociation routes promoted by collision-induced dissociation. The preference for each of the two dissociation pathways, both of which involved cleavage at the midpoint of the hexamer, correlated with the stereochemical configurations (syn versus anti) of the THF groups near the termini.
• Vicinal Tetrahydrofuranyl Substitution of Alkyl Chains. Tetra-, Penta-, and Hexafunctionalized Arrays
  作者：Leo A. Paquette、Naoki Ohmori、Timothy B. Lowinger、Robin D. Rogers

  DOI：10.1021/jo0001075

  日期：2000.7.1

  The tetrakis (tetrahydrofuranyl) dialdehydes 14 and 19 are accessible by oxidative cleavage of extensively substituted cyclohexenes, which have in turn been assembled in a stereocontrolled manner. Reaction of 14 with an excess of the Normant reagent followed by ring closure resulted in conversion to the hexafunctionalized polyether 15. Allylindation of the same dialdehyde gave rise to lactol 16, a reactivity pattern that was essentially duplicated when 19 was treated with the Normant reagent. Attempts to add allylmagnesium bromide to 19 resulted in operation of a Tishchenko reaction viith formation of lactone 23. By means of X-ray diffraction analysis, it was possible to ascertain the conformation adopted by 20 and 23 in the solid state. In addition, 15 was shown to populate a conformation in which the oxygen are very predominantly in gauche arrangements, this structural preorganization taking place in the absence of any metal ions.