pyridin-2-ylmethanamine-d₄ | 1239598-82-3

• 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: pyridin-2-ylmethanamine-d₄
• 英文别名: N,N,1,1-tetradeuterio-1-pyridin-2-ylmethanamine
• CAS: 1239598-82-3
• 化学式: C₆H₈N₂
• 分子量: 112.111
• InChiKey: WOXFMYVTSLAQMO-KJGQCWIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨甲基吡啶 在 dichloro(μ-chloro)(μ-hydrido)bis(η-p-cymene)diruthenium(II) 、 重水 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以62%的产率得到pyridin-2-ylmethanamine-d₄
  参考文献：
  名称：

  使用D 2 O对胺和氨基酸进行选择性α-氘化

  摘要：

  Monohydrido桥连的钌络合物[{（η 6 - p -cymene）的RuCl} 2（μ-H-μ-Cl）的]催化（催化剂负载：0.5-1摩尔％）伯和仲胺的α选择性氘化，氨基酸和药物分子，使用氧化氘（D 2 O）作为氘源。机理研究表明胺的NH活化，这也是通过中间体的单晶X射线分析确定的。β -氢化物消除在形成亚胺连接的钌中间体和随后的1,3-迁移氘化到亚胺酰胺配位体配体的结果导致选择性氘化在α-CH 2的胺官能团质子提出。

  DOI：

  10.1021/acs.orglett.6b02978

文献信息

• Azaallyl-Containing Moieties As Chelate For Metals
  申请人：Wolczanski Peter T.

  公开号：US20100204473A1

  公开（公告）日：2010-08-12

  The invention relates to di-aryl, di-heteroaryl or aryl-heteroaryl azaallyl compounds that are useful as chelates for metals.

  本发明涉及用作金属螯合剂的二芳基、二杂芳基或芳基-杂芳基氮杂烯化合物。
• C–C Bond Formation and Related Reactions at the CNC Backbone in (smif)FeX (smif = 1,3-Di-(2-pyridyl)-2-azaallyl): Dimerizations, 3 + 2 Cyclization, and Nucleophilic Attack; Transfer Hydrogenations and Alkyne Trimerization (X = N(TMS)₂, dpma = (Di-(2-pyridyl-methyl)-amide))
  作者：Brenda A. Frazier、Valerie A. Williams、Peter T. Wolczanski、Suzanne C. Bart、Karsten Meyer、Thomas R. Cundari、Emil B. Lobkovsky

  DOI：10.1021/ic302783y

  日期：2013.3.18

  Molecular orbital analysis depicts the CNCnb backbone of the smif (1,3-di-(2-pyridy1)-2-azaally1) ligand as having singlet diradical and/or ionic character where electrophilic or nucleophilic attack is plausible. Reversible dimerization of (smif)FeN(SiMe3)(2)} (1) to [(Me3Si)(2)N}Fe](2)(mu-K-3,K-3-N,py(2)-smif,smif) (2) may be construed as diradical coupling. A proton transfer within the backbone-methylated, and o-pyridine-methylated smif of putative ((b)Me(2)(0)Me(2)smif)Fe-N(SiMe3)(2) (8) provides a route to [(Me3Si)(2)N}Fe](2)(mu-K-4,K-4-N,py(2),C-(Me-b,(CH2)-C-b,Me-0(2)(smif)H))(2) (9). A 3 + 2 cyclization of ditolyl-acetylene occurs with 1, leading to the dimer [2,5-di(pyridin-2-yl)-3,4-di-(p-tolyl-2,5-dihydropyrrol-1-ide)}FeN-(SiMe3)(2))(2) (11), and the collateral discovery of allcyne cyclotrimerization led to a brief study that identified Fe(N(SiMe3)(2)(THF) as an effective catalyst. Nucleophilic attack by (smif)(2)Fe (13) on 'BuNCO and (2,6-Pr2C6H3)NCO afforded (RNHCO-smif)(2)Fe (14a, R = 'Bu; 14b, 2,6-' PrC6H3). Calculations suggested that (dpma)(2)Fe (15) would favorably lose dihydrogen to afford (smif)(2)Fe (13). H-2-transfer to allcynes, olefins, imines, PhN=NPh, and ketones was explored, but only stoichiometric reactions were affected. Some physical properties of the compounds were examined, and X-ray structural studies on several dinuclear species were conducted.
• US8846919B2
  申请人：——

  公开号：US8846919B2

  公开（公告）日：2014-09-30
• Selective α-Deuteration of Amines and Amino Acids Using D₂O
  作者：Basujit Chatterjee、Varadhan Krishnakumar、Chidambaram Gunanathan

  DOI：10.1021/acs.orglett.6b02978

  日期：2016.11.18

  Monohydrido-bridged ruthenium complex [(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] catalyzes (catalyst load: 0.5–1 mol %) α-selective deuteration of primary and secondary amines, amino acids, and drug molecules using deuterium oxide (D2O) as a deuterium source. Mechanistic investigations revealed N–H activation of amines, which was also established by single-crystal X-ray analysis of an intermediate. β-Hydride

  Monohydrido桥连的钌络合物[（η 6 - p -cymene）的RuCl} 2（μ-H-μ-Cl）的]催化（催化剂负载：0.5-1摩尔％）伯和仲胺的α选择性氘化，氨基酸和药物分子，使用氧化氘（D 2 O）作为氘源。机理研究表明胺的NH活化，这也是通过中间体的单晶X射线分析确定的。β -氢化物消除在形成亚胺连接的钌中间体和随后的1,3-迁移氘化到亚胺酰胺配位体配体的结果导致选择性氘化在α-CH 2的胺官能团质子提出。