(S)-O-(tert-Butyldimethylsilyl)-dec-1-yn-3-ol | 150621-02-6

• 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)-dec-1-yn-3-ol
• 英文别名: tert-butyl-[(3S)-dec-1-yn-3-yl]oxy-dimethylsilane
• CAS: 150621-02-6
• 化学式: C₁₆H₃₂OSi
• 分子量: 268.515
• InChiKey: IKBAWKQLPRRZSO-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-O-(tert-Butyldimethylsilyl)-dec-1-yn-3-ol 在 四(三苯基膦)钯 吡啶 、 copper(l) iodide 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 正丁胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.83h， 生成 Petrosyne Ib triacetate
  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 咪唑 、 正丁基锂 、 草酰氯 、 氢气 、 二甲基亚砜 、 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 25.75h， 生成 (S)-O-(tert-Butyldimethylsilyl)-dec-1-yn-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

文献信息

• <i>tert</i>-Butyldimethylsilyl-Directed Highly Enantioselective Approach to Axially Chiral α-Allenols
  作者：Juntao Ye、Wu Fan、Shengming Ma

  DOI：10.1002/chem.201201948

  日期：2013.1.7

  A highly efficient and enantioselective synthesis of axially chiral α‐allenols was realized in practical yields with 96–99 % ee or de from TBS‐protected propargylic alcohols, aldehydes, and a commercially available, inexpensive, chiral, secondary amine (S)‐α,α‐diphenylprolinol or its enantiomer followed by desilylation. The easily removable TBS group not only acts as a protecting group, but also as

  从TBS保护的炔丙醇，醛和市售的廉价手性仲胺（S）-α中以96-99％ee或de的实际收率实现了轴向手性α-烯醇的高效和对映选择性合成 ，α-二苯基脯氨醇或其对映异构体，然后进行去甲硅烷基化。易于除去的TBS基团不仅充当保护基团，而且还充当可能的空间定向基团，以实现出色的对映选择性并就地防止可能的烯丙基外消旋化。
• Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions
  作者：Zhiyong Chen、Subhash C. Sinha

  DOI：10.1016/j.tet.2007.11.089

  日期：2008.2

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.
• 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).