(2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dienal | 960290-68-0

• 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-dienal
• 英文别名: (2S,4Z,7Z)-2-[tert-butyl(dimethyl)silyl]oxydeca-4,7-dienal
• CAS: 960290-68-0
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: WKRCGDUYHQDLOR-DXDAJUGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 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-dienal 在 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 正丁基锂 、 cerium(III) chloride heptahydrate 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 乙腈 为溶剂， 反应 4.5h， 生成 (5Z,8S,9E,11S,12S,14Z,17Z)-12-(tert-butyldimethylsiloxy)-11-hydroxyicos-5,9,14,17-tetraen-8-olide
  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 、 草酰氯 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 23.83h， 生成 (2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dienal
  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。
• Asymmetric Synthesis of 14-A_4t-Neuroprostane:  Hunting for a Suitable Biomarker for Neurodegenerative Diseases
  作者：Giuseppe Zanoni、Enrico M. Brunoldi、Alessio Porta、Giovanni Vidari

  DOI：10.1021/jo701719f

  日期：2007.12.1

  describe the first total synthesis of 14-A4t-NeuroP in an enantioselective and stereoselective fashion, by means of a new and rapid approach for the installation of the ω chain based on a chemoselective Julia−Kocienski olefination. Furthermore, the construction of the 4,5-cis-disubstituted cyclopentenone moiety characteristic of class A neuroprostanes is achieved in a stereospecific fashion, and suitable

  长期以来，氧化应激与衰老和与年龄有关的病理（例如神经退行性疾病）有关。体内氧化应激的直接作用之一是通过活性氧对膜磷脂的作用形成称为异前列腺素的前列腺素样化合物。由二十二碳六烯酸（C22：6ω3，DHA）形成的异前列腺素的一个特殊亚类，称为神经前列腺素，被认为对神经元氧化应激具有特异性。由于异前列腺素被认为是氧化应激的黄金标准，并且由于神经前列腺素在神经元中对这种状况的特异性及其与阿尔茨海默氏病和帕金森氏病的关系，因此可以预见它们将是这些病理学的合适生物标志物。在这里，我们描述了14-A 4t的第一个全合成-NeuroP以对映选择性和立体选择性的方式，通过一种新的快速方法来安装基于化学选择性Julia-Kocienski烯烃的ω链。此外，以立体特异性方式实现了A类神经前列腺素特征性的4，5-顺式-二取代的环戊烯酮部分的构建，并且已经调整了合适的反应条件以避免不稳定的立体异构中心的差向异构化。
• 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.