3-(5-Hexenyl)pyridine | 29883-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(5-Hexenyl)pyridine
• 英文别名: 5-(pyridin-3-yl)-hex-1-ene；3-(hex-5-enyl)pyridine；6-(3-Pyridyl)-1-hexen；3-Hex-5-enylpyridine
• CAS: 29883-73-6
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: WVJAPLFBRNKDOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  264.9±19.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(5-Hexenyl)pyridine 在 sodium periodate 、 四氧化锇 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以73%的产率得到5-(吡啶-3-基)-戊醛
  参考文献：
  名称：

  Total synthesis of cytotoxic sponge alkaloids hachijodines F and G

  摘要：

  The total synthesis of two cytotoxic sponge alkaloids hachijodines F and G has been achieved. The synthesis of both compounds utilises a common intermediate alkyne. By comparison of spectra the structure of the natural product has been confirmed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00115-7
• 作为产物：
  描述：

  在 乙酸铵 作用下， 以 正丁醇 为溶剂， 以92%的产率得到3-(5-Hexenyl)pyridine
  参考文献：
  名称：

  Reaction of Aldimine Anions with Vinamidinium Chloride:  Three-Component Access to 3-Alkylpyridines and 3-Alkylpyridinium Salts and Access to 2-Alkyl Glutaconaldehyde Derivatives

  摘要：

  [GRAPHICS]N-tert-Butylimino derivatives of aldehydes were deprotonated with LDA and reacted with vinamidinium chloride to give 2-alkylaminopentadienimine derivatives, which were isolated as their corresponding hydrochloride in 68-81% yield. Reaction of these derivatives with ammonium acetate or salts of primary amines, in n-butanol at 80 degrees C, afforded the corresponding 3-alkylpyridines or 3-alkylpyridinium salts in high yield. Alkaline hydrolysis of 2-alkylaminopentadieneimine derivatives allowed a practical accesss to potassium salts of 2-alkylglutaconaldehyde.

  DOI：

  10.1021/jo702311k

文献信息

• B(C₆ F₅ )₃ -Catalyzed Cascade Reduction of Pyridines
  作者：Zhi-Yun Liu、Zhi-Hui Wen、Xiao-Chen Wang

  DOI：10.1002/anie.201702304

  日期：2017.5.15

  development hinges upon the realization of a cascade process of dearomative hydrosilylation (or hydroboration) and transfer hydrogenation. The broad functional‐group tolerance (e.g. ketone, ester, unactivated olefins, nitro, nitrile, heterocycles, etc.) implies high practical utility.

  已发现B（C 6 F 5）3是一种有效的催化剂，可以用氢化硅烷（或氢硼烷）和胺作为还原剂还原吡啶和其他电子不足的N-杂芳烃。该开发的成功取决于脱芳香氢化硅烷化（或硼氢化）和转移氢化的级联过程的实现。宽泛的官能团耐受性（例如酮，酯，未活化的烯烃，硝基，腈，杂环等）暗示着很高的实用性。
• A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents
  作者：Tian Qin、Josep Cornella、Chao Li、Lara R. Malins、Jacob T. Edwards、Shuhei Kawamura、Brad D. Maxwell、Martin D. Eastgate、Phil S. Baran

  DOI：10.1126/science.aaf6123

  日期：2016.5.13

  carbon-carbon bonds are often the hardest to make. Most reactions owe their efficiency to neighboring double bonds or oxygen and nitrogen atoms that linger in the products. Qin et al. now present a broadly applicable protocol for making C-C bonds in the absence of such surrounding help. The nickel-catalyzed process couples a zinc-activated carbon center to an ester that's poised to lose CO2. The ready availability

  没有有用的邻居的碳链接现代有机化学的一个讽刺是，看起来最简单的碳-碳键往往是最难形成的。大多数反应的效率归因于产物中残留的邻近双键或氧和氮原子。秦等人。现在提出了一个广泛适用的协议，用于在没有此类周围帮助的情况下制作 CC 债券。镍催化过程将锌活性炭中心与准备失去二氧化碳的酯偶联。多种羧酸（很容易转化为酯）的现成可用性有助于该反应的多功能性。科学，本期第 14 页。 801 一种多功能的镍催化反应形成碳-碳键，产品中不需要相邻的功能。烷基羧酸在化学科学的各个方面无处不在，从天然产物到聚合物，是建立新联系的理想起始材料。这项研究展示了几十年来用于通过失去水的羧酸形成简单的 C-N（酰胺）键的相同活化原理如何通过与二烷基锌试剂偶联并失去二氧化碳来形成 C-C 键。这种断开策略受益于使用简单、廉价的镍催化剂，并且在一系列基材上表现出非常广泛的范围（>70 示例）。
• C3‐Cyanation of Pyridines: Constraints on Electrophiles and Determinants of Regioselectivity
  作者：Ming Zhang、Qingyang Zhou、Heng Luo、Zi‐Lu Tang、Xiufang Xu、Xiao‐Chen Wang

  DOI：10.1002/anie.202216894

  日期：2023.2

  C3-selective cyanation of pyridines was accomplished by a tandem process of borane-catalyzed pyridine hydroboration, substitution of the resulting dihydropyridine with a cyano electrophile, and finally oxidative aromatization. This method was suitable for use in late-stage cyanation of pyridine drugs.

  吡啶的 C3 选择性氰化是通过硼烷催化的吡啶硼氢化、用氰基亲电试剂取代所得二氢吡啶、最后氧化芳构化的串联过程完成的。该方法适用于吡啶类药物的后期氰化反应。
• The use of chemical probes to differentiate between polar and SET-hydrogen atom abstraction pathways involved in the reduction reaction promoted by an 8-Al-4 anion
  作者：Dennis D. Tanner、C. M. Yang

  DOI：10.1021/jo00074a014

  日期：1993.10

  The mechanism for the reduction of aromatic ketones and alkyl halides with lithium tetrakis(N-dihydropyridyl)aluminate was found to proceed competitively by hydride reduction and by single electron transfer (SET)-hydrogen atom abstraction processes. A series of ketyl fragmentation probes were used to differentiate the two pathways. A SET process is the dominant pathway when the ketones involved are sterically hindered or when strong electron acceptors are used as the substrates. The observation that EPR-active intermediates can be detected, or that small amounts of radical derived products are formed, demonstrates only that a SET pathway is available but cannot be used to establish the mechanism of the major product-forming reactions.
• Bispyridinium Dienes:  Histone Deacetylase Inhibitors with Selective Activities
  作者：Carlos Pérez-Balado、Angela Nebbioso、Paula Rodríguez-Graña、Annunziata Minichiello、Marco Miceli、Lucia Altucci、Ángel R. de Lera

  DOI：10.1021/jm070028m

  日期：2007.5.1

  A novel synthetic route to the cyclostellettamines 1 using as the key step a microwave-mediated macrocyclic ring-closing metathesis of precursors bispyridinium dienes 10 followed by catalytic hydrogenation has been developed. The open-chain bispyridinium dienes 10 showed uniformly higher histone deacetylase (HDAC) inhibitory potency than the natural products. Diene 10b inhibited HDAC1 and was inactive on HDAC4, whereas 10a showed a weak inhibition of HDAC1 and a higher activity on HDAC4. Neither 10b nor 10a inhibited isoforms HDAC2 and HDAC3. Cell cycle analysis, cell differentiation, and apoptosis as well as evaluation of the acetylation status of H3 lysine tails, up-regulation of p21(WAF1/CIP1), and R-tubulin acetylation induced by the dienes 10 and cyclostellettamines 1 were also carried out on the human leukemia U937 cell line. These enzymatic and functional assays suggest that 10b is a HDAC1-selective inhibitor and 10a is a HDAC subclass IIa-selective inhibitor.