β-4(20)-epoxy-5-hydroxytriacetyltaxicin I | 251635-85-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: β-4(20)-epoxy-5-hydroxytriacetyltaxicin I
• 英文别名: [(1'S,2R,2'S,3'R,5'S,8'R,9'R,10'R)-2',9'-diacetyloxy-1',5'-dihydroxy-8',12',15',15'-tetramethyl-13'-oxospiro[oxirane-2,4'-tricyclo[9.3.1.03,8]pentadec-11-ene]-10'-yl] acetate
• CAS: 251635-85-5
• 化学式: C₂₆H₃₆O₁₀
• 分子量: 508.566
• InChiKey: COOMJMHRUQOAAK-HKJFPAPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  β-4(20)-epoxy-5-hydroxytriacetyltaxicin I 在 三异丙氧基氯化钛 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以25%的产率得到[(1S,2S,3S,8R,9R,10S,13S,14R)-2,9-diacetyloxy-3,13-dihydroxy-14-(hydroxymethyl)-6,16,16-trimethyl-5-oxo-8-tetracyclo[8.4.1.13,7.01,10]hexadec-6-enyl] acetate
  参考文献：
  名称：

  (iPrO)3TiCl-induced reactions of α- and β-4(20)-epoxy-5-hydroxytriacetyltaxicin I

  摘要：

  Chlorolitanium triisopropoxide-induced reaction of alpha-4(20)-epoxy-5-hydroxytriacetyltaxicin I 2 gave a 4-hydroxymethylene-5-one 4 and a 4-hydroxy-4-chloromethylene 5, while the corresponding beta-4(20)-epoxide 3 gave a 3,8-cyclopropane 6 and a 6/8/5 ring system 7. Moreover, boron trifluoride-induced reaction of the a-4(20)epoxide 2 yielded a 6/8/6/7 ring system 8 and an A-ring contracted alcohol derivative 9. Plausible mechanisms of these reactions are proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00707-3
• 作为产物：
  描述：

  5-cinnamoyltriacetyltaxicin I 在 盐酸羟胺 、 sodium acetate 、 二甲基二环氧乙烷 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 60.0h， 生成 β-4(20)-epoxy-5-hydroxytriacetyltaxicin I
  参考文献：
  名称：

  (iPrO)3TiCl-induced reactions of α- and β-4(20)-epoxy-5-hydroxytriacetyltaxicin I

  摘要：

  Chlorolitanium triisopropoxide-induced reaction of alpha-4(20)-epoxy-5-hydroxytriacetyltaxicin I 2 gave a 4-hydroxymethylene-5-one 4 and a 4-hydroxy-4-chloromethylene 5, while the corresponding beta-4(20)-epoxide 3 gave a 3,8-cyclopropane 6 and a 6/8/5 ring system 7. Moreover, boron trifluoride-induced reaction of the a-4(20)epoxide 2 yielded a 6/8/6/7 ring system 8 and an A-ring contracted alcohol derivative 9. Plausible mechanisms of these reactions are proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00707-3