5-cinnamoyltriacetyltaxicin I | 148090-72-6

• 英文名称: 5-cinnamoyltriacetyltaxicin I
• 英文别名: 2α,9α,10β-triacetyl-5α-cinnamoyltaxicine I
• CAS: 148090-72-6
• 化学式: C₃₅H₄₂O₁₀
• 分子量: 622.712
• InChiKey: VBLNERPSGWCFQJ-ROLYQHHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  45.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  142.5
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-cinnamoyltriacetyltaxicin I 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 242.0h， 生成 (3aS,7aR,10aR,10bR,13S,14aR,14bS)-2,2,6,9,9,10b,15,15-octamethyl-14-methylene-5-oxo-5,7a,10a,10b,11,12,13,14,14a,14b-decahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d:5,6-d']bis([1,3]dioxole)-13-yl 3-phenylacrylate
  参考文献：
  名称：

  Première hémisynthèse d'un composé de type taxane porteur d'un groupement oxétane en 4(20),5.

  摘要：

  The 1,2,9,10-diO-isopropylidene derivative of 2,4,9,10,13-pentadeacetyl-7-deacetoxybaccatin IV has been prepared in nine steps from taxine B, previously transformed in 2-alpha,9-alpha,10-beta-triacetyl-5-alpha-cinnamoyltaxicine I. The stereoselective reduction of the ketonic group in position 13 provides finally a molecule with an oxetane ring at positions 4(20),5 and the esterifiable hydroxyle in 13-alpha position, both being proved to be necessary to the antitumoral activity of the taxol.

  DOI：

  10.1016/s0040-4020(01)80721-3

文献信息

• Rearranged taxanes from Taxus baccata
  作者：Giovanni Appendino、Giancarlo Cravotto、Renata Enriù、Jasmin Jakupovic、Pierluigi Gariboldi、B. Gabetta、E. Bombardell

  DOI：10.1016/s0031-9422(00)97085-7

  日期：1994.5

  Abstract The needles of Taxus baccata gave two rearranged taxanes of the 11 (15 → 1)- and 2 (3 → 20) abeo -type. A taxicin I triester was also isolated.

  摘要 红豆杉的针叶产生了两种重排的 11 (15 → 1)- 和 2 (3 → 20) abeo 型紫杉烷。还分离了一种出租车素三酯。
• (iPrO)3TiCl-induced reactions of α- and β-4(20)-epoxy-5-hydroxytriacetyltaxicin I
  作者：Qian Cheng、Takayuki Oritani、Tohru Horiguchi

  DOI：10.1016/s0040-4020(99)00707-3

  日期：1999.10

  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.