tributyl((1E,3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)buta-1,3-dienyl)stannane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: tributyl((1E,3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)buta-1,3-dienyl)stannane
• 英文别名: 2-((1E,3E)-4-(tributylstannyl)buta-1,3-dienyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane；2-((1E,3E)-4-(tributylstannyl)buta-1,3-dienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；tributyl-[(1E,3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)buta-1,3-dienyl]stannane
• 化学式: C₂₂H₄₃BO₂Sn
• 分子量: 469.103
• InChiKey: ZBEVVAJCXOEONR-XIZNWYPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tributyl((1E,3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)buta-1,3-dienyl)stannane 、 4-碘代苯乙酮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 P(furyl)3 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以89%的产率得到1-(4-((1E,3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)buta-1,3-dienyl)phenyl)ethanone
  参考文献：
  名称：

  Tandem Stille/Suzuki−Miyaura Coupling of a Hetero-Bis-metalated Diene. Rapid, One-Pot Assembly of Polyene Systems

  摘要：

  The synthesis of a hetero-bis-metallo 1,3-butadiene is reported, and its use as an orthogonal Stille and Suzuki-Miyaura coupling partner is detailed. The tin/boron diene participated successfully in a one-pot, sequential Stille and Suzuki-Miyaura coupling protocol, and its utility was demonstrated in the two-step construction of the pentaene side chain of the Fusarium metabolite lucilactaene.

  DOI：

  10.1021/ol050768u
• 作为产物：
  描述：

  (E)-3-(tri-n-butylstannyl)-2-propen-1-ol 在 MnO₂ 、 CrCl₂ 、 LiI 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tributyl((1E,3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)buta-1,3-dienyl)stannane
  参考文献：
  名称：

  Efficient synthesis of diverse hetero-bis-metallated alkenes as modular reagents towards highly conjugated and isolated olefinic systems

  摘要：

  报道了一种高效合成多样性杂双金属化烯烃的方法，这些烯烃具有共轭和孤立的烯烃亚单位。依靠这些有用的锡/硼试剂，开发了一种收敛的、钯催化的片段偶联策略，作为构建高度共轭的聚烯烃及其稳定的烯烃类似物的优雅方法。这些试剂的实用性进一步通过简明且模块化的构建强效多酮类抗生素etnangien的延伸聚烯烃侧链得到了验证。

  DOI：

  10.1039/c2cc34052f
• 作为试剂：
  描述：

  、 tributyl((1E,3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)buta-1,3-dienyl)stannane 在 tributyl((1E,3E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)buta-1,3-dienyl)stannane 作用下， 生成
  参考文献：
  名称：

  J. Med. Chem. 2010, 53, 7967-7978

  摘要：

  DOI：

文献信息

• (+)-Rimocidin Synthetic Studies: Construction of the C(1−27) Aglycone Skeleton
  作者：Amos B. Smith、Megan A. Foley、Shuzhi Dong、Alia Orbin

  DOI：10.1021/jo900765p

  日期：2009.8.21

  Assembly of the C(1−27) macrocyclic skeleton of rimocidinolide, the aglycone of (+)-rimocidin (1), has been achieved in convergent fashion. Key features of the synthetic strategy entail application of multicomponent Type I Anion Relay Chemistry (ARC), in conjunction with the SN2/SN2′ reaction manifolds of vinyl epoxides, both employing 2-substituted 1,3-dithianes to construct the C(1−19) carbon backbone

  雷莫西丁内酯（(+)-雷莫西丁 ( 1 ) 的糖苷配基）的 C(1−27) 大环骨架的组装已以收敛方式实现。该合成策略的主要特点是应用多组分 I 型阴离子中继化学 (ARC)，结合乙烯基环氧化物的S N 2/S N 2' 反应流形，两者均采用 2-取代 1,3-二噻烷来构建C(1−19) 碳主链。具有全反式三烯的 C(20−27) 硼酸乙烯基酯与先进的 C(1−19) 乙烯基碘化物的 Yamaguchi 结合，然后通过 Suzuki−Miyaura 交叉偶联进行大环化，完成了 C(1− 27)利莫西内酯骨架。
• Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives: Total Synthesis Shows that Putative Orevactaene Is Likely Identical with Epipyrone A
  作者：Johannes Preindl、Saskia Schulthoff、Conny Wirtz、Julia Lingnau、Alois Fürstner

  DOI：10.1002/anie.201702189

  日期：2017.6.19

  Orevactaene and epipyrone A were previously thought to comprise the same polyunsaturated tail but notably different C‐glycosylated 4‐hydroxy‐2‐pyrone head groups. Total synthesis now shows that the signature bicyclic framework assigned to orevactaene is a chimera; the compound is almost certainly identical with epipyrone A, whose previously unknown stereochemistry has also been established during this

  以前认为Orevactaene和Epipyrone A包含相同的多不饱和尾巴，但C-糖基化的4-羟基-2-吡喃酮头基团则明显不同。现在，全合成表明，分配给orevactaene的标志性双环骨架是嵌合体。该化合物几乎可以肯定与Epipyrone A相同，而Epipyrone A在本研究中也已建立了以前未知的立体化学。成功的关键是通过使用钨和金催化的两个炔烃环异构化反应的序列，可以容易地形成推定的前内酯的双环核。同样重要的是，通过使用异双金属多不饱和模块获得的组装过程中的灵活性，其末端可以按照实际的一锅交叉耦合顺序进行选择性和连续处理。
• Efficient synthesis of diverse hetero-bis-metallated alkenes as modular reagents towards highly conjugated and isolated olefinic systems
  作者：Mario Altendorfer、Dirk Menche

  DOI：10.1039/c2cc34052f

  日期：——

  An efficient synthesis of diverse hetero-bis-metallated alkenes with conjugated and isolated olefin subunits is reported. Relying on those useful tin/boron reagents a convergent, palladium-catalyzed fragment coupling strategy has been developed as an elegant methodology to construct highly conjugated polyenes and stabilized olefinic analogues thereof. The utility of these reagents was further demonstrated in a concise and modular construction of extended polyene side chains of the potent polyketide antibiotic etnangien.

  报道了一种高效合成多样性杂双金属化烯烃的方法，这些烯烃具有共轭和孤立的烯烃亚单位。依靠这些有用的锡/硼试剂，开发了一种收敛的、钯催化的片段偶联策略，作为构建高度共轭的聚烯烃及其稳定的烯烃类似物的优雅方法。这些试剂的实用性进一步通过简明且模块化的构建强效多酮类抗生素etnangien的延伸聚烯烃侧链得到了验证。
• A Synthetic Small Molecule F240B Decreases NLRP3 Inflammasome Activation by Autophagy Induction
  作者：Chun-Hsien Wu、Chin Heng Gan、Lan-Hui Li、Jen-Che Chang、Shin-Tai Chen、Mridula P. Menon、Shu-Meng Cheng、Shih-Ping Yang、Chen-Lung Ho、Oleg V. Chernikov、Chi-Hung Lin、Yulin Lam、Kuo-Feng Hua

  DOI：10.3389/fimmu.2020.607564

  日期：——

  Conjugated polyenes are a class of widely occurring natural products with various biological functions. We previously identified 4-hydroxy auxarconjugatin B (4-HAB) as anti‐inflammatory agent with an IC₅₀ of ~20 µM. In this study, we synthesized a new anti‐inflammatory 4-HAB analogue, F240B, which has an IC₅₀ of less than 1 µM. F240B dose-dependently induced autophagy by increasing autophagic flux, LC3 speck formation and acidic vesicular organelle formation. F240B inhibited NACHT, LRR and PYD domain-containing protein 3 (NLRP3) inflammasome activation through autophagy induction. In a mechanistic study, F240B inhibited interleukin (IL)-1β (IL-1β) precursor expression, promoted degradation of NLRP3 and IL-1β, and reduced mitochondrial membrane integrity loss in an autophagy-dependent manner. Additionally, F240B inhibited apoptosis-associated speck-like protein containing a CARD (ASC) oligomerization and speck formation without affecting the interaction between NLRP3 and ASC or NIMA-related kinase 7 (NEK7) and double-stranded RNA-dependent kinase (PKR). Furthermore, F240B exerted in vivo anti-inflammatory activity by reducing the intraperitoneal influx of neutrophils and the levels of IL-1β, active caspase-1, IL-6 and monocyte chemoattractant protein-1 (MCP-1) in lavage fluids in a mouse model of uric acid crystal-induced peritonitis. In conclusion, F240B attenuated the NLRP3 inflammasome through autophagy induction and can be developed as an anti-inflammatory agent in the future.

  共轭聚烯烃是一类广泛存在的天然产物，具有各种生物功能。我们先前确定4-羟基奥克萨康胞素B（4-HAB）为一种抗炎剂，其IC₅₀约为20 µM。在这项研究中，我们合成了一种新的抗炎4-HAB类似物F240B，其IC₅₀小于1 µM。F240B剂量依赖性地通过增加自噬通量、LC3斑点形成和酸性囊泡器官形成诱导自噬。F240B通过诱导自噬抑制了NACHT、LRR和PYD结构域含蛋白3（NLRP3）炎症小体的激活。在一个机制研究中，F240B通过自噬抑制了白细胞介素（IL）-1β（IL-1β）前体的表达，促进了NLRP3和IL-1β的降解，并以自噬依赖的方式减少了线粒体膜完整性的丧失。此外，F240B抑制了与凋亡相关斑点样蛋白含有CARD（ASC）寡聚体化和斑点形成，而不影响NLRP3与ASC或NIMA相关激酶7（NEK7）和双链RNA依赖激酶（PKR）之间的相互作用。此外，F240B通过减少中性粒细胞的腹腔内流入和腹腔灌洗液中IL-1β、活性半胱氨酸蛋白酶-1、IL-6和单核细胞趋化蛋白-1（MCP-1）的水平，在尿酸晶体诱导的腹膜炎小鼠模型中表现出体内抗炎活性。总之，F240B通过诱导自噬减轻了NLRP3炎症小体的作用，并可能成为未来的抗炎剂。
• Total Synthesis of Lucilactaene, A Cell Cycle Inhibitor Active in p53-Inactive Cells
  作者：Robert S. Coleman、Matthew C. Walczak、Erica L. Campbell

  DOI：10.1021/ja056217g

  日期：2005.11.23

  Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.