1-苄基-3-氨基甲酰基吡啶六氟磷酸盐 | 90832-35-2

• 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
• 中文名称: 1-苄基-3-氨基甲酰基吡啶六氟磷酸盐
• 英文名称: 1-benzyl-3-carbamoylpyridinium hexafluorophosphate
• 英文别名: 1-benzylnicotinamidium hexafluorophosphate；1-benzylnicotinamide hexafluorophospate
• CAS: 90832-35-2
• 化学式: C₁₃H₁₃N₂O*F₆P
• 分子量: 358.223
• InChiKey: PYGJCYNSORKBEP-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.97
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-苄基-3-氨基甲酰基吡啶六氟磷酸盐 在 cis-[Ru(bpy)2(CO)(CDO)]PF₆ 作用下， 以 乙腈 为溶剂， 生成 N-benzyl-1,4-dihydronicotinamide
  参考文献：
  名称：

  Konno, Hideo; Sakamoto, Kazuhiko; Ishitani, Osamu, Angewandte Chemie - International Edition, 2000, vol. 39, # 22, p. 4061 - 4063

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(aminocarbonyl)-1-benzylpyridinium bromide 在 六氟磷酸钾 作用下， 以 水 为溶剂， 生成 1-苄基-3-氨基甲酰基吡啶六氟磷酸盐
  参考文献：
  名称：

  烟酰胺辅因子的可见光驱动转移与强健的钌配合物光催化剂

  摘要：

  在钌络合物Ru（tpy）（biq）Cl 2（tpy = 2时）下，通过光催化转移氢化，成功实现了烟酰胺辅因子的高效再生，量子产率（Φ）为7.9×10 -3。 2'：6'，2''-吡啶和biq = 2,2'-双喹啉）。该光催化系统不仅高效，而且对氨基酸残基具有耐受性。这种光催化剂与谷氨酸脱氢酶的结合使得L的可控和有效合成成为可能-谷氨酸待实现。已经提出了涉及光诱导的配体交换，脱羧和氢化物转移的机理。动力学同位素实验揭示的脱羧的[Ru（TPY）（BIQ）HCOO] +到的[Ru（TPY）（BIQ）H] +是速率决定步骤与3.2±0.4千卡mol的小表观活化能- 1。通过反应平衡估计[Ru（tpy）（biq）H] +的水合度为40±3 kcal mol -1。

  DOI：

  10.1039/d0gc00331j
• 作为试剂：
  描述：

  1-benzyl-2,4-dimethyl-1,4-dihydronicotinamide 在 1-苄基-3-氨基甲酰基吡啶六氟磷酸盐 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以75%的产率得到1-benzyl-2,4-dimethyl-3-carbamoylpyridinium hexafluorophosphate
  参考文献：
  名称：

  乙腈中 NADH/NAD+ 类似物的热力学特性：2-甲基、4-甲基和 2,4-二甲基 1-苄基-二氢烟酰胺和相应的吡啶鎓种类

  摘要：

  详细说明了合成标题化合物的程序。然后定量测定每个甲基取代所带来的热力学变化。在乙腈中，NADH 和 NAD+ 类似物各自的单电子氧化和单电子还原电位是通过直接和间接（使用二茂铁介质）循环伏安法获得的。正式氢化物转移的氧化还原电位是从类似物之间发生的平衡反应的研究中推导出来的。随之而来的是阳离子自由基的 pKa。关键词：NADH/NAD+ 甲基化类似物，单电子转移，氢化物转移，热力学。

  DOI：

  10.1139/v95-068

文献信息

• A novel type of hydride-transfer photocatalysis by Ru^II–pyridine complexes: regiocontrolled reduction of an NAD(P) model compound by triethylamine
  作者：Osamu Ishitani、Nobuyo Inoue、Kazuhide Koike、Takashi Ibusuki

  DOI：10.1039/c39940000367

  日期：——

  [Ru(trpy)(bpy)(py)]2+(trpy = 2,2′ : 6′,2″-terpyridine, bpy = 2,2′-bipyridine, py = pyridine) and [Ru(LL)2(py)2]2+(LL = a bidentate ligand) photocatalysed the regiocontrolled reduction of 1-benzyl-4-carbamoyle-pyridinium cation to the dihydro form with no formation of the half-reduced dimers, the photocatalysis proceeds through the photosubstitution of a py ligand of the Ru complexes and the subsequent photoformation of [Ru(trpy)(bpy)H]+ or [Ru(LL)2(py)H]+.

  [Ru(trpy)(bpy)(py)]2+（trpy = 2,2â² ：6,2â²,2â³-三吡啶，bpy = 2,2â²-联吡啶，py = 吡啶）和[Ru(LL)2(py)2]2+（LL = 双齿配体）光催化了 1-苄基-4-氨基甲酰基吡啶阳离子以二氢形式的区域控制还原，没有形成半还原二聚体、光催化是通过光取代 Ru 复合物中的 py 配体并随后光转化为 [Ru(trpy)(bpy)H]+ 或 [Ru(LL)2(py)H]+。
• Effects of base on oxidation of an NADH model compound by iron(III) complexes and tetracyanoethylene
  作者：Shunichi Fukuzumi、Yuji Kondo、Toshio Tanaka

  DOI：10.1039/p29840000673

  日期：——

  Effects of base on both an electron-transfer reaction from an NADH model compound, 1-benzyl-1,4-dihydronicotinamide (BNAH) to [Fe(N–N)3]3+(N–N = 2,2′-bipyridine and 1,10-phenanthroline) and a hydride transfer from BNAH to tetracyanoethylene (TCNE) in acetonitrile have been examined. The stroicheiometry of the electron transfer from BNAH to [Fe(N–N)3]3+ in the absence of a base indicates that BNAH is

  碱对NADH模型化合物1-苄基-1,4-二氢烟酰胺（BNAH）到[Fe（N–N）3 ] 3+（N–N = 2,2'-联吡啶和1,10-菲咯啉）和氢化物从BNAH到乙腈中的四氰基乙烯（TCNE）的转移已得到检验。在没有碱的情况下从BNAH到[Fe（N–N）3 ] 3+的电子转移的分光光度法表明BNAH是单电子供体。然而，在存在碱的情况下，当通过多个步骤进行两电子转移时，BNAH充当明显的两电子供体。从BNA˙到[Fe（N–N）3 ] 3+的快速单电子转移。已经确定了质子从BNAH + +转移到一系列吡啶衍生物的速率常数。在通过BNAH降低TCNE的过程中，在不存在和存在碱的情况下，BNAH似乎都是​​两电子供体。BNAH降低TCNE的速率随碱浓度的增加而增加，表明BNAH + ˙作为氢化物从BNAH到TCNE转移的中间体。动力学分析已导致对BNAH + ˙的各种碱去质子化的质子传递速率常数的
• Hydride Reduction of NAD(P)⁺ Model Compounds with a Ru(II)–Hydrido Complex
  作者：Kichitaro Koga、Yasuo Matsubara、Tatsumi Kosaka、Kazuhide Koike、Tatsuki Morimoto、Osamu Ishitani

  DOI：10.1021/acs.organomet.5b00713

  日期：2015.12.14

  In order to better understand the regioselective hydride transfer of metal hydrido complexes to NAD(P)(+) model compounds, reactions of [Ru(tpy)(bpy)H](+) (Ru-H: tpy = 2,2':6 '',2 ''-terpyridine, bpy = 2,2'-bipyridine) with various substituent NAD(P)(+) model compounds were investigated in detail. All of the NAD(P)(+) model compounds accepted hydride from Ru-H, yielding 1:1 adducts, where the dihydro form(s) of the model compounds coordinated with the carbamoyl group to the Ru(II) center of [Ru(tpy)(bpy)](2+), with very different reaction rates. Some reactions produced the adduct with only the 1,4-dihydro structure, whereas others produced a mixture of two adducts, with a 1,4- or 1,2-dihydro structure. In particular, temperature-dependent adduct formation kinetics studies provided important information on the transition state(s) of the hydride transfer reactions and factors for determining the regioselectivity. Most adducts were cleaved to the corresponding free dihydro product(s) with the same distribution of the regioisomers to the adduct(s).
• Hydricities of BzNADH, C₅H₅Mo(PMe₃)(CO)₂H, and C₅Me₅Mo(PMe₃)(CO)₂H in Acetonitrile
  作者：William W. Ellis、James W. Raebiger、Calvin J. Curtis、Joseph W. Bruno、Daniel L. DuBois

  DOI：10.1021/ja038567d

  日期：2004.3.1

  The thermodynamic hydride donor abilities of 1-benzyl-1,4-dihydronicotinamide (BzNADH, 59 +/- 2 kcal/mol), C5H5Mo(PMe3)(CO)(2)H (55 +/- 3 kcal/mol), and C5Me5Mo(PMe3)(CO)(2)H (58 +/- 2 kcal/mol) have been measured in acetonitrile by calorimetric and/or equilibrium methods. The hydride donor abilities of BzNADH and C5H5Mo(PMe3)(CO)2H differ by 13 and 24 kcal/mol, respectively, from those reported previously for these compounds in acetonitrile. These results require significant revisions of the hydricities reported for related NADH analogues and metal hydrides. These compounds are moderate hydride donors as compared to previously determined compounds.
• Formation of Novel 1:1 Adducts Accompanied by Regioselective Hydride Transfer from Transition-Metal Hydrido Complexes to NAD(P) Models
  作者：Atsuo Kobayashi、Ryosuke Takatori、Itsumi Kikuchi、Hideo Konno、Kazuhiko Sakamoto、Osamu Ishitani

  DOI：10.1021/om010362v

  日期：2001.8.1

  Important intermediates in regioselective hydride reduction of NAD(P) model compounds were detected by various spectroscopic methods. The metal hydrido complexes [Ru(tpy)(bpy)H](+) and [Re(bpy)-(CO)(3)H] react with the NAD(P) models to give 1:1 adducts, which are cleaved to the 1,4-dihydro form of the models and the solvento complexes, quantitatively.