Petrosyne Ib | 150999-02-3

• 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: Petrosyne Ib
• 英文别名: (2S)-3-[(Z,7S)-7-hydroxytetradec-1-en-3,5-diynoxy]propane-1,2-diol
• CAS: 150999-02-3
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: UQBZQMCQRZYTLU-ZDSADJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 Petrosyne Ib 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以41%的产率得到(R)-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)-1-O-Benzylnonane-1,2-diol 在 palladium on activated charcoal 、 四(三苯基膦)钯 吡啶 、 咪唑 、 copper(l) iodide 、 正丁基锂 、 草酰氯 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 lithium carbonate 、 二甲基亚砜 、 正丁胺 、 三乙胺 、 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 47.58h， 生成 Petrosyne Ib
  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

文献信息

• Structure and synthesis of petrosynes, new acetylenic enol ether glycerides from the Okinawan marine sponge of the genus Petrosia
  作者：Kazuo Iguchi、Makoto Kitade、Toshihiko Kashiwagi、Yasuji Yamada

  DOI：10.1021/jo00073a030

  日期：1993.10

  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).