2-(2,4:3,5-di-O-benzylidene-D-glycero-D-allo-pentitol-1-yl)pyridine | 38838-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-(2,4:3,5-di-O-benzylidene-D-glycero-D-allo-pentitol-1-yl)pyridine
• 英文别名: 2-(2,4:3,5-di-O-benzylidene-D-allo-pentitol-1-yl)pyridine；(S)-[(4S,4aR,8aR)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]-pyridin-2-ylmethanol
• CAS: 38838-20-9；38838-21-0；150521-44-1
• 化学式: C₂₄H₂₃NO₅
• 分子量: 405.45
• InChiKey: GCYKKTRLXKLNLO-VRXJECTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,4:3,5-di-O-benzylidene-D-glycero-D-allo-pentitol-1-yl)pyridine 在 溶剂黄146 作用下， 反应 2.25h， 以61%的产率得到2-(D-allo-pentitol-1-yl)pyridine
  参考文献：
  名称：

  Synthesis of 2-( d - allo - and d - altro -pentitol-1-yl)pyridines and their 2′,5′-anhydro derivatives

  摘要：

  DOI：

  10.1016/s0008-6215(00)90909-1
• 作为产物：
  描述：

  2-吡啶基锂 、 2-(2,4:3,5-di-O-benzylidenepentitol-1-yl)pyridine 以 四氢呋喃 为溶剂， 生成 2-(2,4:3,5-di-O-benzylidene-D-altro-pentitol-1-yl)pyridine 、 2-(2,4:3,5-di-O-benzylidene-D-glycero-D-allo-pentitol-1-yl)pyridine
  参考文献：
  名称：

  2-(2,4:3,5-Di-O-benzylidene-D-glycero-D-allo-pentitol-1-yl)pyridine, C₂₄H₂₃NO₅

  摘要：

  C24H23NO5, M(r) = 405.4, orthorhombic, P2(1)2(1)2(1), a = 8.762 (1), b = 13.984 (1), c = 16.569 (1) angstrom, V = 2030 (1) angstrom3, Z = 4, D(x) = 1.327 Mg m-3, lambda(Mo Kalpha) = 0.71073 angstrom, mu = 0.087 mm-1, F(000) = 856, room temperature, wR = 0.034, R = 0.035 for 2049 observed reflections [I greater-than-or-equal-to 3sigma(I)] out of 2536 measured reflections and 341 variables. The sugar moiety has the D-allo configuration, which provides further proof that the ring closure of the title compound to an a-nucleoside follows an S(N)2-like mechanism. The title compound consists of two 1,3-dioxane rings in the chair form, trans fused to each other, with two phenyl rings and a (2-pyridyl)hydroxymethyl substituent in equatorial positions. The variation of the C-O lengths in the dioxane rings follows the rules of the anomeric effect. The 1,3-dioxane rings are more puckered than their carbon analogues in transdecalin. The pyridine ring is nearer to C(3) than to O(2), with a synclinal conformation around C(1)C(2). An intermolecular hydrogen bond is observed, but no intramolecular hydrogen bonds were found. Molecular-mechanics calculations (MM3 force field) reproduce the bond lengths with an e.s.d. of 0.011 angstrom and the valence angles with an e.s.d. of 1.0-degrees. MM3 supports conclusions drawn from the X-ray determination concerning the conformational behaviour of the free molecule. In the force field the absence of parameters dedicated to aromatic N atoms makes calculations more difficult.

  DOI：

  10.1107/s0108768192013296