diethyl 6,7-bis(tert-butyldimethylsilyl)oxy-2(E),10(E)-dodecadienedioate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl 6,7-bis(tert-butyldimethylsilyl)oxy-2(E),10(E)-dodecadienedioate
• 英文别名: diethyl (2E,6R,7R,10E)-6,7-bis[[tert-butyl(dimethyl)silyl]oxy]dodeca-2,10-dienedioate
• 化学式: C₂₈H₅₄O₆Si₂
• 分子量: 542.904
• InChiKey: ILCDMDOGCGSAFS-RCOUAKNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 6,7-bis(tert-butyldimethylsilyl)oxy-2(E),10(E)-dodecadienedioate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 3.0h， 以78%的产率得到6,7-bis(tert-butyldimethylsilyl)oxy-2(E),10(E)-dodecadiene-1,12-diol
  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 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.67h， 生成 diethyl 6,7-bis(tert-butyldimethylsilyl)oxy-2(E),10(E)-dodecadienedioate
  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.