5-[Tert-butyl(dimethyl)silyl]oxy-2,6,6-trimethylcyclohexene-1-carbaldehyde | 209069-55-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5-[Tert-butyl(dimethyl)silyl]oxy-2,6,6-trimethylcyclohexene-1-carbaldehyde
• CAS: 209069-55-6
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: NZWXFGIAAJNRAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[Tert-butyl(dimethyl)silyl]oxy-2,6,6-trimethylcyclohexene-1-carbaldehyde 在 sodium tetrahydroborate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (+/-)-2-hydroxy-β-cyclogeraniol
  参考文献：
  名称：

  Stereo- and regio-selective Ti-mediated radical cyclization of epoxy-alkenes: synthesis of the A and C ring synthons of paclitaxel

  摘要：

  We have developed a practical synthetic route for the A and C rings of paclitaxel. The key reaction is a Ti-mediated radical cyclization of an epoxyalkene. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01655-0
• 作为产物：
  描述：

  5-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde 在 silica gel 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.2h， 生成 5-[Tert-butyl(dimethyl)silyl]oxy-2,6,6-trimethylcyclohexene-1-carbaldehyde
  参考文献：
  名称：

  A novel approach to the Taxol A-ring synthetic equivalents

  摘要：

  A novel short approach to the A-ring synthetic equivalents of Taxol was described. Oxabicyclic ketone 3 served as a versatile template for selective functionalization leading to oxabicyclic vinylic ether 6 in two steps, which was hydrolyzed under mild acidic conditions to afford the hydroxy aldehyde derivative 7. Synthetic equivalents 2 of Taxol A-ring were thus, accessible from hydroxy aldehyde 7. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.061

文献信息

• Synthesis of A-ring fragments of 1α,25-dihydroxyvitamin D3 and taxane diterpenoids: Effective construction of conjugated formylcyclohexene frameworks from isoxazolines
  作者：Teruhiko Ishikawa、Shushiro Ikeda、Masataka Ibe、Seiki Saito

  DOI：10.1016/s0040-4020(98)00273-7

  日期：1998.5

  This paper have delineated the effectiveness of [3+2] cycloaddition process in the synthesis of multifunctional 6-membered rings. The novel synthesis of chiral A-ring fragment of 1 alpha,25-dihydroxyvitamin D-3 and also a novel route to A-ring fragment of taxane diterpenoids have been established. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A novel approach to the Taxol A-ring synthetic equivalents
  作者：Zhang-Hua Gao、Bing Liu、Wei-Dong Z. Li

  DOI：10.1016/j.tet.2005.08.061

  日期：2005.11

  A novel short approach to the A-ring synthetic equivalents of Taxol was described. Oxabicyclic ketone 3 served as a versatile template for selective functionalization leading to oxabicyclic vinylic ether 6 in two steps, which was hydrolyzed under mild acidic conditions to afford the hydroxy aldehyde derivative 7. Synthetic equivalents 2 of Taxol A-ring were thus, accessible from hydroxy aldehyde 7. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereo- and regio-selective Ti-mediated radical cyclization of epoxy-alkenes: synthesis of the A and C ring synthons of paclitaxel
  作者：Kazuoki Nakai、Miyuki Kamoshita、Takayuki Doi、Haruo Yamada、Takashi Takahashi

  DOI：10.1016/s0040-4039(01)01655-0

  日期：2001.10

  We have developed a practical synthetic route for the A and C rings of paclitaxel. The key reaction is a Ti-mediated radical cyclization of an epoxyalkene. (C) 2001 Elsevier Science Ltd. All rights reserved.