1-(pyridin-4-yl)heptan-1-ol | 91553-73-0

• 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: 1-(pyridin-4-yl)heptan-1-ol
• 英文别名: 1-Pyridin-4-ylheptan-1-ol
• CAS: 91553-73-0
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: ZYNHFYZPFAGNJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(pyridin-4-yl)heptan-1-ol 在 potassium permanganate 、 magnesium sulfate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 4-庚酰基吡啶
  参考文献：
  名称：

  Comparative inhibition of tetrameric carbonyl reductase activity in pig heart cytosol by alkyl 4-pyridyl ketones

  摘要：

  Context and objective: The present study is to elucidate the comparative inhibition of tetrameric carbonyl reductase (TCBR) activity by alkyl 4-pyridyl ketones, and to characterize its substrate-binding domain.Materials and methods: The inhibitory effects of alkyl 4-pyridyl ketones on the stereoselective reduction of 4-benzoylpyridine (4-BP) catalyzed by TCBR were examined in the cytosolic fraction of pig heart.Results: Of alkyl 4-pyridyl ketones, 4-hexanoylpyridine, which has a straight-chain alkyl group of five carbon atoms, inhibited most potently TCBR activity and was a competitive inhibitor. Furthermore, cyclohexyl pentyl ketone, which is substituted by cyclohexyl group instead of phenyl group of hexanophenone, had much lower ability to be reduced than hexanophenone.Discussion and conclusion: These results suggest that in addition to a hydrophobic cleft corresponding to a straight-chain alkyl group of five carbon atoms, a hydrophobic pocket with affinity for an aromatic group is located in the substrate-binding domain of TCBR.

  DOI：

  10.3109/14756366.2013.790021
• 作为产物：
  描述：

  4-吡啶甲醛 、 己基溴化镁 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1-(pyridin-4-yl)heptan-1-ol
  参考文献：
  名称：

  Comparative inhibition of tetrameric carbonyl reductase activity in pig heart cytosol by alkyl 4-pyridyl ketones

  摘要：

  Context and objective: The present study is to elucidate the comparative inhibition of tetrameric carbonyl reductase (TCBR) activity by alkyl 4-pyridyl ketones, and to characterize its substrate-binding domain.Materials and methods: The inhibitory effects of alkyl 4-pyridyl ketones on the stereoselective reduction of 4-benzoylpyridine (4-BP) catalyzed by TCBR were examined in the cytosolic fraction of pig heart.Results: Of alkyl 4-pyridyl ketones, 4-hexanoylpyridine, which has a straight-chain alkyl group of five carbon atoms, inhibited most potently TCBR activity and was a competitive inhibitor. Furthermore, cyclohexyl pentyl ketone, which is substituted by cyclohexyl group instead of phenyl group of hexanophenone, had much lower ability to be reduced than hexanophenone.Discussion and conclusion: These results suggest that in addition to a hydrophobic cleft corresponding to a straight-chain alkyl group of five carbon atoms, a hydrophobic pocket with affinity for an aromatic group is located in the substrate-binding domain of TCBR.

  DOI：

  10.3109/14756366.2013.790021

文献信息

• Reductive Arylation of Aliphatic and Aromatic Aldehydes with Cyanoarenes by Electrolysis for the Synthesis of Alcohols
  作者：Xiao Zhang、Chao Yang、Han Gao、Lei Wang、Lin Guo、Wujiong Xia

  DOI：10.1021/acs.orglett.1c00920

  日期：2021.5.7

  An electroreductive arylation reaction of aliphatic and aromatic aldehydes as well as ketones with electro-deficient (hetero)arenes is described. A variety of cyano(hetero)arenes and carbonyl compounds, especially aliphatic aldehydes, have been examined, providing secondary and tertiary alcohols in moderate to good yields. Mechanistic studies, including cyclic voltammetry (CV), electron paramagnetic

  描述了脂族和芳族醛以及酮与电缺陷（杂）芳烃的电还原芳基化反应。已经研究了各种氰基（杂）芳烃和羰基化合物，尤其是脂肪族醛，以中等到良好的收率提供了仲醇和叔醇。包括循环伏安法（CV），电子顺磁共振（EPR）和分裂细胞实验在内的机理研究均支持通过阴极还原再进行自由基-自由基交叉偶联来生成脂肪族酮基和持久性杂芳基阴离子。
• Hydropyridylation of α,β-Unsaturated Esters through Electroreduction of 4-Cyanopyridine
  作者：Hua-Jian Zhou、Jing-Mei Huang

  DOI：10.1021/acs.joc.2c00177

  日期：2022.4.15

  A mild and highly efficient method for the hydropyridylation of α,β-unsaturated esters has been developed. This protocol provides the products smoothly with a wide substrate scope in an undivided cell under ambient conditions. Moreover, studies showed that the scope could be extended to other unsaturated compounds, including enones and aldehydes.

  开发了一种温和高效的α,β-不饱和酯加氢吡啶化方法。该协议在环境条件下在未分裂的细胞中顺利地为产品提供了广泛的底物范围。此外，研究表明范围可以扩展到其他不饱和化合物，包括烯酮和醛。
• 10.1039/d4ob00268g
  作者：Kaur, Milanpreet、Cooper, Julian C.、Van Humbeck, Jeffrey F.

  DOI：10.1039/d4ob00268g

  日期：——

  Benzylic C–H bonds can be converted into numerous functional groups, often by mechanisms that involve hydrogen atom transfer as the key bond breaking step. The abstracting species is most often an electrophilic radical, which makes these reactions best suited to electron-rich C–H bonds to achieve appropriate polarity matching. Thus, electron deficient systems such as pyridine and pyrimidine are relatively

  苄基 C-H 键可以转化为许多官能团，通常通过涉及氢原子转移作为关键键断裂步骤的机制。抽象物质通常是亲电子自由基，这使得这些反应最适合富电子的 C-H 键，以实现适当的极性匹配。因此，缺电子系统（例如吡啶和嘧啶）相对不活泼，因此在底物范围中代表性不足。在本报告中，我们描述了一种杂苄羟基化的新方法（对于嘧啶来说本质上是一种未知的反应），该方法利用碘（ III ）试剂对具有多个反应性的底物中的缺电子氮杂环提供非常高的选择性位置并防止过度氧化成羰基产物。关键反应副产物的鉴定支持了在成键步骤中涉及自由基偶联的机制。
• Comparative inhibition of tetrameric carbonyl reductase activity in pig heart cytosol by alkyl 4-pyridyl ketones
  作者：Hideaki Shimada、Takahiro Tanigawa、Kazunori Matayoshi、Kazufumi Katakura、Ken Babazono、Hiroyuki Takayama、Tsuyoshi Murahashi、Hiroyuki Akita、Toshiyuki Higuchi、Masashi Eto、Yorishige Imamura

  DOI：10.3109/14756366.2013.790021

  日期：2014.6.1

  Context and objective: The present study is to elucidate the comparative inhibition of tetrameric carbonyl reductase (TCBR) activity by alkyl 4-pyridyl ketones, and to characterize its substrate-binding domain.Materials and methods: The inhibitory effects of alkyl 4-pyridyl ketones on the stereoselective reduction of 4-benzoylpyridine (4-BP) catalyzed by TCBR were examined in the cytosolic fraction of pig heart.Results: Of alkyl 4-pyridyl ketones, 4-hexanoylpyridine, which has a straight-chain alkyl group of five carbon atoms, inhibited most potently TCBR activity and was a competitive inhibitor. Furthermore, cyclohexyl pentyl ketone, which is substituted by cyclohexyl group instead of phenyl group of hexanophenone, had much lower ability to be reduced than hexanophenone.Discussion and conclusion: These results suggest that in addition to a hydrophobic cleft corresponding to a straight-chain alkyl group of five carbon atoms, a hydrophobic pocket with affinity for an aromatic group is located in the substrate-binding domain of TCBR.