4,8-di-(tosyloxymethyl)-1,3,5,7-cis-tetraoxadecalin | 7465-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,8-di-(tosyloxymethyl)-1,3,5,7-cis-tetraoxadecalin
• 英文别名: O²,O⁴;O³,O⁵-dimethanediyl-O¹,O⁶-bis-(toluene-4-sulfonyl)-D-mannitol；O²,O⁴;O³,O⁵-Dimethandiyl-O¹,O⁶-bis-(toluol-4-sulfonyl)-D-mannit；[(4R,4aR,8R,8aR)-4-[(4-methylphenyl)sulfonyloxymethyl]-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-8-yl]methyl 4-methylbenzenesulfonate
• CAS: 7465-84-1
• 化学式: C₂₂H₂₆O₁₀S₂
• 分子量: 514.574
• InChiKey: GDTIUDCPGLAYJW-GXRSIYKFSA-N

物化性质

• 沸点：
  673.1±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,8-di-(tosyloxymethyl)-1,3,5,7-cis-tetraoxadecalin 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以90%的产率得到4,8-dimethyl-1,3,5,7-cis-tetraoxadecalin
  参考文献：
  名称：

  Substituent effects on the conformational equilibrium of 1,3,5,7-cis-tetraoxadecalin systems: Force field calculations Versus experimental results

  摘要：

  Conformer populations of a number of 1,3,5,7-cis-tetraoxadecalins have been studied by H-1 NMR spectroscopy. While the unsubstituted 4 prefers the proximal conformation, all 4,8 disubstituted derivatives 5 preferred the distal conformation. This was most marked for the di-azidomethyl derivative 5g. Force field calculations were shown to reproduce only roughly the trends of the conformer equilibria. Changing the solvent from toluene-D-8 to more polar solvents increases the population of the proximal conformer.

  DOI：

  10.1016/0957-4166(95)00366-w
• 作为产物：
  描述：

  1,6-di-O-benzoyl-2,4:3,5-di-O-methylene-D-mannitol 在 吡啶 、 甲醇 、 sodium methylate 作用下， 生成 4,8-di-(tosyloxymethyl)-1,3,5,7-cis-tetraoxadecalin
  参考文献：
  名称：

  23.山梨糖醇和甘露糖醇的二苯甲酸酯及其亚甲基衍生物

  摘要：

  DOI：

  10.1039/jr9440000058

文献信息

• Haskins; Hann; Hudson, Journal of the American Chemical Society, 1943, vol. 65, p. 73
  作者：Haskins、Hann、Hudson

  DOI：——

  日期：——
• Vargha et al., Journal of the Chemical Society, 1957, p. 805,809
  作者：Vargha et al.

  DOI：——

  日期：——
• 110. Dithiols. Part IV. The reaction of toluene-p-sulphonates and methanesulphonates with potassium thiolacetate: a new method for the preparation of thiols
  作者：J. H. Chapman、L. N. Owen

  DOI：10.1039/jr9500000579

  日期：——
• Substituent effects on the conformational equilibrium of 1,3,5,7-cis-tetraoxadecalin systems: Force field calculations Versus experimental results
  作者：A.Gil Santos、Reinhard W. Hoffmann

  DOI：10.1016/0957-4166(95)00366-w

  日期：1995.11

  Conformer populations of a number of 1,3,5,7-cis-tetraoxadecalins have been studied by H-1 NMR spectroscopy. While the unsubstituted 4 prefers the proximal conformation, all 4,8 disubstituted derivatives 5 preferred the distal conformation. This was most marked for the di-azidomethyl derivative 5g. Force field calculations were shown to reproduce only roughly the trends of the conformer equilibria. Changing the solvent from toluene-D-8 to more polar solvents increases the population of the proximal conformer.
• 23. The dibenzoates of sorbitol and mannitol and their methylene derivatives
  作者：W. N. Haworth、L. F. Wiggins

  DOI：10.1039/jr9440000058

  日期：——