1-(4'-cyanobiphenyl-2-yl)pentan-1-ol | 1206489-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4'-cyanobiphenyl-2-yl)pentan-1-ol
• CAS: 1206489-09-9
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: YOHNMPOPTUEZGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  44.02
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 为溶剂， 反应 1.0h， 以92 mg的产率得到1-(4'-cyanobiphenyl-2-yl)pentan-1-ol
  参考文献：
  名称：

  Unification of Anion Relay Chemistry with the Takeda and Hiyama Cross-Coupling Reactions: Identification of an Effective Silicon-Based Transfer Agent

  摘要：

  The unification of Anion Relay Chemistry (ARC) with the Takeda and Hiyama palladium-mediated cross-coupling processes to provide aryl aryl, alkenyl aryl, and alkenyl alkenyl coupled products by exploiting a common silicon-based transfer agent has been achieved. These results provide a practical solution for intermolecular cross-coupling of organolithium reagents without the problematic lithium halogen exchange and/or undesired homocoupling that has kept organolithium cross-couplings from achieving the same level of utility as other palladium-mediated methods (e.g., Suzuki organoboron, Negishi organozinc, Stale organotin, Kumada organomagnesium, etc.).

  DOI：

  10.1021/ja2120103

文献信息

• Anion Relay Chemistry: Access to the Type II ARC Reaction Manifold through a Fundamentally Different Reaction Pathway Exploiting 1-Oxa-2-silacyclopentanes and Related Congeners
  作者：Amos B. Smith、Rongbiao Tong、Won-Suk Kim、William A. Maio

  DOI：10.1002/anie.201103886

  日期：2011.9.12

  congener have been synthesized and demonstrated to provide access to type II anion relay chemistry (ARC) through a fundamentally new mechanistic pathway. Similar to previous studies, but contrary to initial hypothesis, Brook rearrangement additives (hexamethylphosphoramide and CuI) are necessary to promote Si migration and anion capture.

  截然不同：两种 1-氧杂-2-硅杂环戊烯和一种饱和同系物已被合成，并被证明可以通过一种全新的机制途径提供 II 型阴离子中继化学 (ARC)。与之前的研究类似，但与最初的假设相反，Brook 重排添加剂（六甲基磷酰胺和 CuI）对于促进 Si 迁移和阴离子捕获是必要的。
• Uniting Anion Relay Chemistry with Pd-Mediated Cross Coupling: Design, Synthesis and Evaluation of Bifunctional Aryl and Vinyl Silane Linchpins
  作者：Amos B. Smith、Won-Suk Kim、Rongbiao Tong

  DOI：10.1021/ol902784q

  日期：2010.2.5

  Union of type II Anion Relay Chemistry (ARC) with Pd-induced Cross Coupling Reactions (CCR) has been achieved, in conjunction with the design, synthesis, and evaluation of a new class of bifunctional linchpins, comprising a series of vinyl silanes bearing β- or γ-electrophilic sites. The synthetic tactic permits both alkylation and Pd-mediated CCR of the anions derived via 1,4-silyl C(sp2)→O Brook

  II 型阴离子继电器化学 (ARC) 与 Pd 诱导的交叉偶联反应 (CCR) 结合，结合设计、合成和评估一类新型双功能关键，包括一系列带有 β 的乙烯基硅烷- 或 γ-亲电位点。合成策略允许通过 1,4-甲硅烷基 C(sp 2 )→O 布鲁克重排衍生的阴离子的烷基化和 Pd 介导的 CCR 。