(2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dien-1-ol | 960290-62-4

• 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: (2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dien-1-ol
• 英文别名: (2S,4Z,7Z)-2-[tert-butyl(dimethyl)silyl]oxydeca-4,7-dien-1-ol
• CAS: 960290-62-4
• 化学式: C₁₆H₃₂O₂Si
• 分子量: 284.514
• InChiKey: PPURTDRBRCZTFX-DXDAJUGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dien-1-ol 在 N-碘代丁二酰亚胺 、 草酰氯 、 potassium carbonate 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.16h， 生成 methyl (2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dienoate
  参考文献：
  名称：

  Synthesis of marine oxylipin topsentolide A1 and its stereoisomers, and determination of the absolute configuration of the natural product

  摘要：

  Four possible stereoisomers of topsentolide A(1), a cytotoxic oxylipin against human solid tumor cell lines, were efficiently synthesized in a stereoselective manner in order to determine the stereochemistry of natural product. The absolute configuration of topsentolide A(1) was determined to be 8R,11R,12S by comparing NMR spectra and specific rotations of the synthetic isomers and the natural product. Cytotoxicity of the synthetic isomers was also examined. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.013
• 作为产物：
  描述：

  (Z)-hex-3-en-1-yltriphenylphosphonium iodide 在 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.67h， 生成 (2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dien-1-ol
  参考文献：
  名称：

  Synthesis of marine oxylipin topsentolide A1 and its stereoisomers, and determination of the absolute configuration of the natural product

  摘要：

  Four possible stereoisomers of topsentolide A(1), a cytotoxic oxylipin against human solid tumor cell lines, were efficiently synthesized in a stereoselective manner in order to determine the stereochemistry of natural product. The absolute configuration of topsentolide A(1) was determined to be 8R,11R,12S by comparing NMR spectra and specific rotations of the synthetic isomers and the natural product. Cytotoxicity of the synthetic isomers was also examined. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.013

文献信息

• Synthesis of Marine Oxylipins Constanolactones C and D
  作者：Jörg Pietruszka、Anja Rieche、Niklas Schöne

  DOI：10.1055/s-2007-986647

  日期：2007.10

  After providing the marine oxylipins constanolactones A and B, the next two members of this family were synthesized for the first time. Key to the success was a highly enantioselective and Z-selective reagent-controlled allyl addition (>99%) en route to the aliphatic side chain.

  在提供海洋oxylipins constanolactones A和B之后，该家族的下两个成员首次被合成。成功的关键是高度对映选择性和 Z 选择性试剂控制的烯丙基加成 (>99%) 到脂肪族侧链。
• Determination of the absolute configuration of marine oxylipin topsentolide A1 by the synthesis of the enantiomer of the natural product
  作者：Munetaka Kobayashi、Ken Ishigami、Hidenori Watanabe

  DOI：10.1016/j.tetlet.2010.03.071

  日期：2010.5

  Two possible stereoisomers of topsentolide A(1), a cytotoxic oxylipin against human solid tumor cell lines, were prepared in order to determine the stereochemistry of natural product. That is, the enantiomer of topsentolide A(1), (85,115,12R)-isomer, and its diastereomer was efficiently synthesized in a stereoselective manner. The stereochemistry of topsentolide A(1) was determined to be 8R,11R,12S by comparing NMR spectra and specific rotations of the synthetic isomers and the natural product. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of marine oxylipin topsentolide A1 and its stereoisomers, and determination of the absolute configuration of the natural product
  作者：Ken Ishigami、Munetaka Kobayashi、Motoki Takagi、Kazuo Shin-ya、Hidenori Watanabe

  DOI：10.1016/j.tet.2015.09.013

  日期：2015.11

  Four possible stereoisomers of topsentolide A(1), a cytotoxic oxylipin against human solid tumor cell lines, were efficiently synthesized in a stereoselective manner in order to determine the stereochemistry of natural product. The absolute configuration of topsentolide A(1) was determined to be 8R,11R,12S by comparing NMR spectra and specific rotations of the synthetic isomers and the natural product. Cytotoxicity of the synthetic isomers was also examined. (C) 2015 Elsevier Ltd. All rights reserved.