(S)-O-(tert-Butyldimethylsilyl)-1,1-dibromodec-1-en-3-ol | 150621-00-4

• 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: (S)-O-(tert-Butyldimethylsilyl)-1,1-dibromodec-1-en-3-ol
• CAS: 150621-00-4
• 化学式: C₁₆H₃₂Br₂OSi
• 分子量: 428.323
• InChiKey: IULZYALEMDEPRX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.37
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-O-(tert-Butyldimethylsilyl)-1,1-dibromodec-1-en-3-ol 在 四(三苯基膦)钯 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 lithium carbonate 、 正丁胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.33h， 生成 (S)-3-<<1-<(S,Z)-7-Hydroxytetradec-1-ene-3,5-diynyl>>oxy>propane-1,2-diol tris-(R)-α-methoxy-α-(trifluoromethyl)phenylacetate
  参考文献：
  名称：

  Structure and synthesis of petrosynes, new acetylenic enol ether glycerides from the Okinawan marine sponge of the genus Petrosia

  摘要：

  Acetylenic enol ether glycerides, 1 and 3, were found in the Okinawan marine sponge of the genus Petrosia. The plane structures of these glycerides were deduced from spectroscopic analysis. Their complete structures were established by enantioselective total synthesis of all possible stereoisomers using (R)-1-O-benzylglycerol and its (S)-enantiomer, prepared from D-mannitol and L-ascorbic acid, respectively, as chiral building blocks. The synthesis involves the palladium(O)-catalyzed coupling reaction of bromo enol ether 9 with enediyne 21 as a key step. It became evident from the synthesis that the natural product 1 consisted of a mixture of (7R,2'S)-24 (petrosyne Ia) and (7S,2S)-24 (petrosyne Ib), and the natural product 3 consisted of a mixture of (7R,2'S)-28 (petrosyne IIa) and (7S,2'S)-28 (petrosyne IIb).

  DOI：

  10.1021/jo00073a030
• 作为产物：
  描述：

  (S)-2-O-(tert-Butyldimethylsilyl)nonane-1,2-diol 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 反应 5.25h， 生成 (S)-O-(tert-Butyldimethylsilyl)-1,1-dibromodec-1-en-3-ol
  参考文献：
  名称：

  Structure and synthesis of petrosynes, new acetylenic enol ether glycerides from the Okinawan marine sponge of the genus Petrosia

  摘要：

  Acetylenic enol ether glycerides, 1 and 3, were found in the Okinawan marine sponge of the genus Petrosia. The plane structures of these glycerides were deduced from spectroscopic analysis. Their complete structures were established by enantioselective total synthesis of all possible stereoisomers using (R)-1-O-benzylglycerol and its (S)-enantiomer, prepared from D-mannitol and L-ascorbic acid, respectively, as chiral building blocks. The synthesis involves the palladium(O)-catalyzed coupling reaction of bromo enol ether 9 with enediyne 21 as a key step. It became evident from the synthesis that the natural product 1 consisted of a mixture of (7R,2'S)-24 (petrosyne Ia) and (7S,2S)-24 (petrosyne Ib), and the natural product 3 consisted of a mixture of (7R,2'S)-28 (petrosyne IIa) and (7S,2'S)-28 (petrosyne IIb).

  DOI：

  10.1021/jo00073a030