| 146356-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 146356-69-6；146356-70-9；146451-47-0；146451-48-1
• 化学式: C₃₄H₆₀O₆Si₂
• 分子量: 621.018
• InChiKey: WYGWHAQWCWCFNC-NEEKEDPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.92
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 四丁基氟化铵 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 (1S,2R,9S,10S)-2-Hydroxy-4,9,10-trimethoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3(8),4,6,11-tetraen-13-one
  参考文献：
  名称：

  An Efficient Approach toward Taxane Analogs: Atrop- and Diastereoselective Eight-Membered B Ring Cyclizations for Synthesis of Aromatic C-Ring Taxinine Derivatives

  摘要：

  We have developed efficient methods for construction of the C-2 oxygenated aromatic C-ring taxane skeleton based on an eight-membered ring cyclization involving a Lewis acid-mediated intramolecular coupling reaction of the dienol silyl ether at C-10 and the acetal at C-9. The C-2 stereogenic center strongly influences the conformation of the forming eight-membered ring during the cyclization reaction. 1 beta,2 alpha-Siloxy derivative 13b gives exo isomer 15 as the major product, and 1 beta,2 beta-siloxy derivative 13a exclusively yields endo isomer 14. Both of these cyclization products, which had undesired stereochemistry, were converted to stereochemically refined aromatic C-ring taxinine analogs by multistep transformations. The chelation-controlled, eight-membered ring cyclization of 1 beta,2 alpha-hydroxy derivative 31 was found to give exclusively the desired 1 beta,2 alpha,9 alpha,10 beta-endo isomer 16 in good yield. This remarkably stereoselective cyclization, when combined with stereocontrolled AC ring coupling reactions, should provide an efficient, convergent route toward various taxane derivatives. The aromatic C-ring taxinine analogs could be converted to natural taxinine by further transformation of the aromatic C-ring.

  DOI：

  10.1021/jo00090a039
• 作为产物：
  描述：

  Acetic acid 5-formyl-2,4,4-trimethyl-3-oxo-cyclohex-1-enyl ester 在 四氢吡咯 、 cerium(III) chloride 、 potassium tert-butylate 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  C-芳族紫杉碱衍生物的合成

  摘要：

  2-位（紫杉烷编号）的含氧取代基对确定内/外环化进入紫杉烷骨架中涉及的 8 元环系统起着关键作用，芳香紫杉碱衍生物由相应的 2α,9β 制备，通过热外向异构化和路易斯酸诱导的 C-9 和 C-10 位点反转，10α-外环化化合物。

  DOI：

  10.1246/cl.1993.133

文献信息

• The seven-membered ring intermediate to control the stereochemistry on the eight-membered taxane B ring cyclization
  作者：Koichiro Morihira、Masaki Seto、Takashi Furukawa、Yoshiaki Horiguchi、Isao Kuwajima

  DOI：10.1016/s0040-4039(00)60584-1

  日期：1993.1

  On 8-membered ring cyclization of taxane B ring, formation of 7-membered cyclized intermediate has been identified, and the unique cyclization as well as the isomerization mechanism involving several equilibration processes have been proposed

  在紫杉烷B环的8元环化反应中，已经确定了7元环化中间体的形成，并提出了独特的环化以及涉及多个平衡过程的异构化机理