1-(1-adamantylcarbonylmethyl)pyridinium bromide | 17760-81-5

• 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-(1-adamantylcarbonylmethyl)pyridinium bromide
• 英文别名: adamantane carbomethylpyridinium bromide；1-adamantane carbomethylpyridinium bromide；1-[2-(1-adamantyl)-2-oxoethyl]pyridinium bromide；1-[2-oxo-2-(tricyclo[3.3.1.1^3,7]dec-1-yl)ethyl]pyridinium bromide；1-[2-(adamantan-1-yl)-2-oxoethyl]pyridin-1-ium bromide；1-Adamantanoylmethylpyridinium bromide；1-(1-adamantyl)-2-pyridin-1-ium-1-ylethanone;bromide
• CAS: 17760-81-5
• 化学式: Br*C₁₇H₂₂NO
• 分子量: 336.272
• InChiKey: VCFMXNKUSRQFHG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-adamantylcarbonylmethyl)pyridinium bromide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 为溶剂， 反应 0.08h， 以91%的产率得到pyridinium (1-adamantylcarbonyl)methylide
  参考文献：
  名称：

  Reactions of o-Quinone Methides with Pyridinium Methylides: A Diastereoselective Synthesis of 1,2-Dihydronaphtho[2,1-b]furans and 2,3-Dihydrobenzofurans

  摘要：

  A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.

  DOI：

  10.1021/jo400621r
• 作为产物：
  描述：

  吡啶 、 1-金刚烷基溴甲酮 反应 3.0h， 以69%的产率得到1-(1-adamantylcarbonylmethyl)pyridinium bromide
  参考文献：
  名称：

  由环糊精二聚体和双位客体分子制备超分子聚合物：通过接头柔性控制结构。

  摘要：

  已经使用β-环糊精二聚体和具有金刚烷基的二位客体二聚体制备了基于环糊精的超分子聚合物。制备具有各种柔韧性和金刚烷基部分的对位客体二聚体以研究超分子聚合物的构象。双位的金刚烷客体二聚体C0具有在金刚烷基之间具有4,4'-联吡啶鎓基团的刚性间隔基。双位的金刚烷客体二聚体C2和C3具有柔性的亚甲基间隔基。带有双位金刚烷客体二聚体的β-环糊精二聚体的ROESY光谱显示金刚烷基取代基的质子与环糊精内部质子之间的NOE。对位金刚烷客体二聚体C2和C3在水溶液中形成环状超分子低聚物。通过原子力显微镜（AFM）观察到循环结构。相反，双位的金刚烷客体二聚体C0形成了高分子量超分子聚合物。

  DOI：

  10.1021/ma0508606

文献信息

• Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid
  作者：Vera А. Shadrikova、Evgeny V. Golovin、Victor B. Rybakov、Yuri N. Klimochkin

  DOI：10.1007/s10593-020-02747-9

  日期：2020.7

  1-[2-(Adamantan-1-yl)-2-hydroxyethyl]-1,2,3,6-tetrahydropyridines were obtained by reduction of 1-[(adamantan-1-yl)-2-oxoethyl]-pyridinium bromides. By the action of trifluoromethanesulfonic acid, they undergo carbocationic intramolecular cyclization accompanied by the Wagner–Meerwein rearrangement with the formation of substituted 1-azabicyclo[3.3.1]non-3-enes annulated with the homoadamantane framework

  通过还原1-[（金刚烷-1-基）-2-氧代乙基]-溴化吡啶得到1- [2-（金刚烷-1-基）-2-羟乙基] -1,2,3,6-四氢吡啶。 。在三氟甲磺酸的作用下，它们经历碳阳离子分子内环化，并伴随Wagner-Meerwein重排，形成被高金刚烷骨架取代的取代的1-azabicyclo [3.3.1] non-3-enes。所得化合物的结构通过光谱法和X射线结构分析确认。
• Three-Component Condensation of Pyridinium Ylides, β-Ketonitriles, and Aldehydes with Divergent Regioselectivity: Synthesis of 4,5-Dihydrofuran-3- and 2<i>H</i>-Pyran-5-carbonitriles
  作者：Maxim R. Demidov、Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/acs.joc.1c00423

  日期：2021.6.4

  and semistabilized pyridinium ylide precursors, and aldehydes in the presence of piperidine. This one-pot transformation generates two C–C and one C–O bond and proceeds through a cascade Knoevenagel condensation, a Michael addition, and intramolecular SN2 cyclization. Formation of cyclopropanecarbonitrile derivatives, which in some cases were obtained as major products, was found to be a competing

  通过β-酮腈、羰基和半稳定化的吡啶鎓叶立德前体以及醛在哌啶存在下的三组分反应，以非对映选择性方式合成了反式-4,5-二氢呋喃-3-甲腈文库。这种一锅转化生成两个C-C和一个C-O键并经由级联Knoevenagel缩合，迈克尔加成，和分子内小号Ñ 2环化。发现在某些情况下作为主要产物获得的环丙烷甲腈衍生物的形成是一种竞争反应。芳基乙二醛的使用会改变区域选择性并产生 2-hydroxy-2 H - pyran -5-carbonitriles。
• Three-component synthesis of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones and their reductive rearrangement into 4H,5H-thiochromeno[4,3-b]pyran-5-ones
  作者：Maxim R. Demidov、Anastasiya N. Dobrokvashina、Dmitry V. Osipov、Vitaly А. Osyanin、Yuri N. Klimochkin

  DOI：10.1007/s10593-021-02944-0

  日期：2021.5

  4-hydroxythiocoumarin led to a series of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones. The reaction proceeds diastereoselectively with the formation of trans-isomers and represents a cascade process involving the Knoevenagel condensation, carbo-Michael reaction, and intramolecular nucleophilic substitution. The subsequent redox rearrangement of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones by the action

  原位生成的吡啶鎓酰基甲基化物与芳香醛和 4-羟基硫香豆素的三组分缩合导致一系列 2-酰基-2,3-二氢-4 H-硫代色基[4,3 - b ]呋喃-4-酮。该反应非对映选择性地进行，形成反式异构体，代表了一个涉及 Knoevenagel 缩合、碳-迈克尔反应和分子内亲核取代的级联过程。随后通过 Zn 和 ZrCl4 的作用对 2-acyl-2,3-dihydro-4 H -thiochromeno[4,3 - b ]furan-4-ones进行氧化还原重排，获得 4 H ,5 H -thiochromeno[4 ,3 - b ]pyran-5-ones。
• Stereoselective Synthesis of<i>trans</i>-2,3-Disubstituted 5-Amino-4-cyano-2,3-dihydrothiophenes
  作者：A. M. Shestopalov、O. P. Bogomolova、V. P. Litvinov

  DOI：10.1055/s-1991-26445

  日期：——

  Interaction of 1-(1-adamantylcarbonylmethyl)pyridinium bromide (1) with arylmethylenecyanothioacetamides 2 proceeds stereoselectively with formation of 2-(1-adamantylcarbonyl)-5-amino-3-aryl-4-cyano-2,3-dihydrothiophenes. Dihydrothiophenes were obtained in a good yield by three-component condensation of pyridinium bromide 1, aldehydes and cyanothioacetamide in presence of triethylamine.

  1-(1-金刚烷基羰基甲基)溴化吡啶鎓（1）与芳基亚甲基硫代氰乙酰胺 2 相互作用，立体选择性地生成 2-(1-金刚烷基羰基)-5-氨基-3-芳基-4-氰基-2,3-二氢噻吩。 在三乙胺存在下，通过溴化吡啶鎓 1、醛类和硫代氰乙酰胺的三组分缩合，可以获得收率很高的二氢噻吩。
• Regio- and diastereoselective synthesis of N-substituted 2-acyl-3-aryl-3,5-dihydrofuro[3,2-c]pyridin-4(2H)-ones
  作者：Evgeny А. Kvetkin、Dmitry V. Osipov、Pavel E. Krasnikov、Vitaly А. Osyanin、Yuri N. Klimochkin

  DOI：10.1007/s10593-020-02832-z

  日期：2020.11

  The three-component condensation of pyridinium acylmethylides generated in situ with aromatic aldehydes and 4-hydroxy-6-methylpyridones gave a series of 2-acyl-3-aryl-3,5-dihydrofuro[3,2-c]pyridin-4(2H)-ones. The reaction proceeds diastereoselectively with the formation of trans-isomers and represents a cascade process involving the Knoevenagel condensation, the carbo-Michael reaction, and intramolecular

  与芳族醛和4-羟基-6-甲基吡啶酮原位生成的吡啶鎓甲基吡啶的三组分缩合反应生成一系列2-酰基-3-芳基-3,5-二氢呋喃[3,2 - c ]吡啶-4（ 2 H）-一。该反应非对映选择性地进行，形成反式异构体，代表级联过程，涉及Knoevenagel缩合，碳-迈克尔反应和分子内亲核取代。