(+/-)-1,2,4-tris(benzoyloxy)butane | 129956-98-5

• 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: (+/-)-1,2,4-tris(benzoyloxy)butane
• 英文别名: 3,4-Dibenzoyloxybutyl benzoate
• CAS: 129956-98-5
• 化学式: C₂₅H₂₂O₆
• 分子量: 418.446
• InChiKey: JRRBIPJIOMRZTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1,2,4-丁三醇 、 苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(+/-)-1,2,4-tris(benzoyloxy)butane
  参考文献：
  名称：

  Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)

  摘要：

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.

  DOI：

  10.1021/jo962166h

文献信息

• Anchimerically assisted lewis acid cleavage of tetrahydrofurans to furnish 1,4-Diols
  作者：Laurence M. Harwood、Brian Jackson、Keith Prout、Fiona J. Witt

  DOI：10.1016/s0040-4039(00)98811-7

  日期：1990.1

  trahydrofurans with TiCl4 results in cleavage of the heterocyclic ring with intervention by the appropriately situated ester group to form intermediates which, on work-up and hydrolysis, furnish 1,4-diols.

  用TiCl 4处理3-芳酰氧基-和2-（芳酰氧基甲基）四氢呋喃可导致杂环的裂解，同时通过适当定位的酯基的干预形成中间体，该中间体在后处理和水解时提供1,4-二醇。
• HARWOOD, LAURENCE M.;JACKSON, BRIAN;PROUT, KEITH;WITT, FIONA J., TETRAHEDRON LETT., 31,(1990) N3, C. 1885-1888
  作者：HARWOOD, LAURENCE M.、JACKSON, BRIAN、PROUT, KEITH、WITT, FIONA J.

  DOI：——

  日期：——
• Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)
  作者：Dale L. Boger、Masataka Hikota、Bryan M. Lewis

  DOI：10.1021/jo962166h

  日期：1997.3.1

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.