(4aR,6R,7R,8aS)-2,2-di(tert-butyl)-7-(triethylsilyloxy)hexahydro-1,3,5-trioxa-2-silanaphthalene-6-carbaldehyde | 865871-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6R,7R,8aS)-2,2-di(tert-butyl)-7-(triethylsilyloxy)hexahydro-1,3,5-trioxa-2-silanaphthalene-6-carbaldehyde
• 英文别名: (4aR,6R,7R,8aS)-2,2-ditert-butyl-7-triethylsilyloxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasiline-6-carbaldehyde
• CAS: 865871-41-6
• 化学式: C₂₁H₄₂O₅Si₂
• 分子量: 430.732
• InChiKey: ILAVEBBWFIUZFH-YDZRNGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aR,6R,7R,8aS)-2,2-di(tert-butyl)-7-(triethylsilyloxy)hexahydro-1,3,5-trioxa-2-silanaphthalene-6-carbaldehyde 在 N-甲基吗啉 、 吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 (E)-(4aR,6R,7R,8aS)-3-{6-[(1R)-1-(acetoxy)propynyl]-2,2-di(tert-butyl)hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yloxy}acrylic acid methyl ester
  参考文献：
  名称：

  A stereoselective route to multi-substituted tetrahydropyrans by vinyl radical cyclization

  摘要：

  The tin-mediated 6-exo-trig radical cyclization of the acetylenic beta-alkoxy acrylates proceeded smoothly to give fully substituted tetrahydropyrans in good yields with high equatorial selectivity irrespective of the stereochemistry of the propargylic position. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.007
• 作为产物：
  描述：

  ((4aR,6S,7R,8aS)-2,2-Di-tert-butyl-7-triethylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-methanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以91%的产率得到(4aR,6R,7R,8aS)-2,2-di(tert-butyl)-7-(triethylsilyloxy)hexahydro-1,3,5-trioxa-2-silanaphthalene-6-carbaldehyde
  参考文献：
  名称：

  A stereoselective route to multi-substituted tetrahydropyrans by vinyl radical cyclization

  摘要：

  The tin-mediated 6-exo-trig radical cyclization of the acetylenic beta-alkoxy acrylates proceeded smoothly to give fully substituted tetrahydropyrans in good yields with high equatorial selectivity irrespective of the stereochemistry of the propargylic position. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.007

文献信息

• Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes
  作者：Yumie Suzuki、Ayano Kuwabara、Yasuhiro Koizumi、Yuji Mori

  DOI：10.1016/j.tet.2013.08.026

  日期：2013.10

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.