6,7-bis(tert-butyldimethylsilyl)oxy-1,12-dibromo-2(E),10(E)-dodecadiene

• 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: 6,7-bis(tert-butyldimethylsilyl)oxy-1,12-dibromo-2(E),10(E)-dodecadiene
• 英文别名: tert-butyl-[(2E,6R,7R,10E)-1,12-dibromo-7-[tert-butyl(dimethyl)silyl]oxydodeca-2,10-dien-6-yl]oxy-dimethylsilane
• 化学式: C₂₄H₄₈Br₂O₂Si₂
• 分子量: 584.623
• InChiKey: XHMHSNYTNLBSTL-VAXYAMPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.23
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,7-bis(tert-butyldimethylsilyl)oxy-1,12-dibromo-2(E),10(E)-dodecadiene 在 氢氟酸 、 碳酸氢钠 作用下， 生成 3,6:7,10-diepoxy-1,11-dodecadiene 、 3,6:7,10-diepoxy-1,11-dodecadiene
  参考文献：
  名称：

  Double Intramolecular S_N‘ O-Cyclization for Stereoselective Synthesis of Bistetrahydrofuran Core of Acetogenins

  摘要：

  A C-2-symmetric bistetrahydrofuran core of acetogenins has been prepared via double intramolecular S-N' O-cyclization reactions. Approaches using readily prepared both E- and Z-olefin substrates are investigated. The cyclization of E-olefins gave a mixture of two diastereomers with low selectivity, while the corresponding Z-olefins predominantly provided a desired trans,trans-bistetrahydrofuran product. The high diastereoselectivity is presumably controlled by a hydrogen-bonding transition state. An efficient enantioselective synthesis of this C-2-symmetric bistetrahydrofuran is also described. Sharpless asymmetric dihydroxylation was used for this approach.

  DOI：

  10.1021/jo981771c
• 作为产物：
  描述：

  (1R,2R)-(Z)-cyclooct-5-ene-1,2-diol 在 咪唑 、 四溴化碳 、 二异丁基氢化铝 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.67h， 生成 6,7-bis(tert-butyldimethylsilyl)oxy-1,12-dibromo-2(E),10(E)-dodecadiene
  参考文献：
  名称：

  Double Intramolecular S_N‘ O-Cyclization for Stereoselective Synthesis of Bistetrahydrofuran Core of Acetogenins

  摘要：

  A C-2-symmetric bistetrahydrofuran core of acetogenins has been prepared via double intramolecular S-N' O-cyclization reactions. Approaches using readily prepared both E- and Z-olefin substrates are investigated. The cyclization of E-olefins gave a mixture of two diastereomers with low selectivity, while the corresponding Z-olefins predominantly provided a desired trans,trans-bistetrahydrofuran product. The high diastereoselectivity is presumably controlled by a hydrogen-bonding transition state. An efficient enantioselective synthesis of this C-2-symmetric bistetrahydrofuran is also described. Sharpless asymmetric dihydroxylation was used for this approach.

  DOI：

  10.1021/jo981771c

文献信息

• Double Intramolecular S_N‘ <i>O</i>-Cyclization for Stereoselective Synthesis of Bistetrahydrofuran Core of Acetogenins
  作者：Pan Li、Jiong Yang、Kang Zhao

  DOI：10.1021/jo981771c

  日期：1999.4.1

  A C-2-symmetric bistetrahydrofuran core of acetogenins has been prepared via double intramolecular S-N' O-cyclization reactions. Approaches using readily prepared both E- and Z-olefin substrates are investigated. The cyclization of E-olefins gave a mixture of two diastereomers with low selectivity, while the corresponding Z-olefins predominantly provided a desired trans,trans-bistetrahydrofuran product. The high diastereoselectivity is presumably controlled by a hydrogen-bonding transition state. An efficient enantioselective synthesis of this C-2-symmetric bistetrahydrofuran is also described. Sharpless asymmetric dihydroxylation was used for this approach.