1-buta-1,3-dienyl-tri-n-butylstannane | 81925-31-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: 1-buta-1,3-dienyl-tri-n-butylstannane
• 英文别名: (E)-1-tri-n-butylstannyl-1,3-butadiene；(E)-buta-1,3-dien-1-yltributylstannane；(E)-buta-1,3-dienyltributylstannane
• CAS: 81925-31-7
• 化学式: C₁₆H₃₂Sn
• 分子量: 343.14
• InChiKey: OEENDSGGUFQDGG-UHFFFAOYSA-N

物化性质

• 沸点：
  335.6±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-buta-1,3-dienyl-tri-n-butylstannane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (E)-butadienyl-lithium
  参考文献：
  名称：

  宏扩展方法：高效的八单元环扩展

  摘要：

  描述了一种有效的八单元环膨胀方法，该方法被假定通过[5,5]或连续的[3,3]σ位移进行。

  DOI：

  10.1016/s0040-4039(01)92935-1
• 作为产物：
  描述：

  三丁基氯化锡 、 生成 1-buta-1,3-dienyl-tri-n-butylstannane
  参考文献：
  名称：

  FRYZUK, M. D.;BATES, G. S.;STONE, CH., TETRAHEDRON LETT., 1986, 27, N 14, 1537-1540

  摘要：

  DOI：

文献信息

• Total Synthesis of the Fungal Metabolite Trienylfuranol A through Nucleophilic Diastereodivergent Additions to Oxocarbenium Ions
  作者：Guillaume Arcile、Pascal Retailleau、Jamal Ouazzani、Jean‐Francois Betzer

  DOI：10.1002/ejoc.202100265

  日期：2021.4.8

  triene‐substituted tetrahydrofuran metabolite is described. The key step, for the installation of the stereogenic center of the trienyl side chain, involves a stereofacially reduction of oxocarbenium ions directed by the hydride donor.

  描述了三烯基呋喃醇A（一种真菌末端三烯取代的四氢呋喃代谢物）的第一次全合成。对于安装三烯基侧链的立体中心的关键步骤，涉及由氢化物供体指导的氧碳en离子的立体表面还原。
• Total Synthesis of Hirsutellone B via Ullmann-Type Direct 13-Membered Macrocyclization
  作者：Hiromi Uchiro、Ryo Kato、Yuuki Arai、Miki Hasegawa、Yu Kobayakawa

  DOI：10.1021/ol202748e

  日期：2011.12.2

  Total synthesis of Hirsutellone B has been achieved by a convergent synthetic strategy. This synthesis features direct construction of the highly strained 13-membered macrocycle of Hirsutellone B utilizing the Ullmann-type reaction. To the best of our knowledge, this is the first application of macrocyclization utilizing an intramolecular Ullmann-type reaction between an aliphatic alcohol and aryl

  通过收敛的合成策略已经实现了Hirsutellone B的全合成。该合成的特征是利用Ullmann型反应直接构建Hirsutellone B的高应变13元大环。据我们所知，这是利用脂族醇与芳基卤化物之间的分子内乌尔曼型反应进行大环化的首次应用。
• Synthetic Studies toward GKK1032s, Novel Antibiotic Antitumor Agents:  Enantioselective Synthesis of the Fully Elaborated Tricyclic Core via an Intramolecular Diels−Alder Cycloaddition
  作者：Moriteru Asano、Munenori Inoue、Kazuhiro Watanabe、Hideki Abe、Tadashi Katoh

  DOI：10.1021/jo0610208

  日期：2006.9.1

  An enantioselective synthesis of the fully elaborated tricyclic decahydrofluorene core (ABC-ring system) of GKK1032s, novel antimicrobial and antitumor agents, has been accomplished for the first time by employing a highly diastereoselective intramolecular Diels−Alder (IMDA) reaction. The key substrate for the IMDA reaction was efficiently prepared through (i) an intermolecular Diels−Alder reaction

  通过高度非对映选择性分子内Diels-Alder（IMDA）反应首次完成了对GKK1032s的详尽阐述的三环十氢芴核（ABC环系统），新型抗微生物剂和抗肿瘤剂的对映选择性合成。通过（i）硅烷氧基二烯与衍生自d-甘露糖醇的旋光烯酮之间的分子间Diels-Alder反应，以构建适当官能化的C环和（ii）CuCl促进的Stille偶联，有效制备了IMDA反应的关键底物（E）-乙烯基碘和乙烯基锡烷的安装，以安装必要的三烯侧链作为关键步骤。
• Enantioselective Synthesis of the Tricyclic Core of GKK1032, Novel Antibiotic Anti-Tumor Agents, by Employing an Intramolecular Diels-Alder Cycloaddition Strategy
  作者：Munenori Inoue、Tadashi Katoh、Moriteru Asano

  DOI：10.1055/s-2005-869843

  日期：——

  enantioselective synthesis of a decahydrofluorene nucleus, the tricyclic core (ABC-ring system) of GKK1032s, novel antimicrobial and anti-tumor agents, was achieved using a highly diastereoselective intramolecular Diels-Alder (IMDA) reaction. The substrate for the IMDA reaction was synthesized through intermolecular Diels-Alder reaction of Kitahara-Danishefsky's diene and an enone derived from enulose to construct

  使用高度非对映选择性的分子内 Diels-Alder (IMDA) 反应实现了十氢芴核、GKK1032s 的三环核心（ABC 环系统）、新型抗菌剂和抗肿瘤剂的高效和对映选择性合成。IMDA 反应的底物是通过 Kitahara-Danishefsky 的二烯和衍生自 enulose 的烯酮的分子间 Diels-Alder 反应合成的，以构建功能化的 C 环。CuCl 促进的乙烯基碘化物和乙烯基锡烷的 Stille 偶联安装了必需的三烯侧链。
• A cycloaddition approach to tricyclic taxoid skeletons
  作者：Yee-Fung Lu、Alex G. Fallis

  DOI：10.1139/v95-278

  日期：1995.12.1

  A cycloaddition approach to the functionalized tricyclo[9.3.1.0^3,8]pentadecene skeleton contained in Taxol® is described. The cyclohexenone 13 was converted as illustrated to the nitrile-aldehyde 24 to which the diene and acetylenic side chains were attached by sequential nucleophilic additions. Removal of the trimethylsilyl protecting group and Dess–Martin oxidation afforded the triene 35. Microwave-assisted thermal cyclization stereoselectively generated the tricyclic ketone 36 whose structure was further established by conversion to the aromatic system 37 upon treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). An epoxidation sequence was developed to introduce the epimeric C13 alcohol 47 as required for this cycloaddition strategy. Alternatively, an allylic oxidation (CrO₃, 3,5-dimethylpyrazole) afforded the C13 ketone 49. Keywords: Taxol®, Diels–Alder, synthesis, diterpene, alkaloid.

  描述了一种用于功能化紫杉醇中含有的三环[9.3.1.0^3,8]戊二十烯骨架的环加成方法。将环己烯酮13转化为腈醛24，然后通过顺序亲核加成将二烯和乙炔侧链连接到其中。去除三甲基硅保护基和Dess-Martin氧化生成三烯35。微波辅助热环化立体选择性地生成三环酮36，其结构经过与2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)反应转化为芳香系统37进一步确定。开发了一个环氧化序列，引入了所需的环加成策略C13醇47的对映异构体。另外，烯丙基氧化(CrO3, 3,5-二甲基吡唑)生成了C13酮49。关键词：紫杉醇，迪尔斯-阿尔德，合成，二萜，生物碱。