2,2,2-Trideuterio-1-pyridin-2-ylethanone | 59857-06-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trideuterio-1-pyridin-2-ylethanone
• 英文别名: 2,2,2-trideuterio-1-pyridin-2-ylethanone
• CAS: 59857-06-6
• 化学式: C₇H₇NO
• 分子量: 124.115
• InChiKey: AJKVQEKCUACUMD-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰基吡啶 在 重水 、 sodium hydroxide 作用下， 生成 2,2,2-Trideuterio-1-pyridin-2-ylethanone
  参考文献：
  名称：

  d-氨基葡萄糖C-N键的异头立体辅助裂解制备咪唑并[1,5-a]吡啶

  摘要：

  通过七元环过渡态中间体和同时在咪唑并[1,5-a]吡啶中掺入胺部分，实现了一种 α-异头立体辅助策略，用于靶向裂解d-氨基葡萄糖中的 C-N 键。该方法为 C-N 键断裂提供了一种新的策略，并解锁了对具有多种官能团的各种咪唑并[1,5-a] 吡啶块的有效访问。

  DOI：

  10.1002/chem.202200648

文献信息

• METHODS FOR THE SYNTHESIS OF DEUTERATED VINYL PYRIDINE MONOMERS
  申请人：Hong Kunlun

  公开号：US20140024836A1

  公开（公告）日：2014-01-23

  Methods for synthesizing deuterated vinylpyridine compounds of the Formula (1), wherein the method includes: (i) deuterating an acyl pyridine of the Formula (2) in the presence of a metal catalyst and D 2 O, wherein the metal catalyst is active for hydrogen exchange in water, to produce a deuterated acyl compound of Formula (3); (ii) reducing the compound of Formula (3) with a deuterated reducing agent to convert the acyl group to an alcohol group, and (iii) dehydrating the compound produced in step (ii) with a dehydrating agent to afford the vinylpyridine compound of Formula (1). The resulting deuterated vinylpyridine compounds are also described.

  合成公式（1）的氘代乙烯吡啶化合物的方法，其中该方法包括：（i）在金属催化剂和D2O存在下，对公式（2）的酰基吡啶进行氘代反应，其中金属催化剂在水中活性交换氢，以生成公式（3）的氘代酰基化合物；（ii）用氘代还原剂还原公式（3）的化合物，将酰基转化为醇基；（iii）用脱水剂脱水步骤（ii）中产生的化合物，以生成公式（1）的乙烯吡啶化合物。还描述了所得到的氘代乙烯吡啶化合物。
• First-Row Transition Metal and Lithium Pyridine-ene-amide Complexes Exhibiting N- and C-Isomers and Ligand-Based Activation of Benzylic C–H Bonds
  作者：Brian M. Lindley、Peter T. Wolczanski、Thomas R. Cundari、Emil B. Lobkovsky

  DOI：10.1021/acs.organomet.5b00385

  日期：2015.10.12

  Ene-amines Z-3-(2-pyridyl)-1-aza(2,6-Pr-i(2)-Ph)propene, (pynac)H, and 2-(2-pyridy1)-1-aza(2,6-R,R'-Ph)propene, (pyEA-ArRR')H, were synthesized by condensation procedures; corresponding lithium or potassium ene-amides were prepared via standard deprotonation protocols. Addition of 2 equiv of (pynac)H to (Me3Si)(2)N}(2)Fe(THF) or 2 Li(pynac) to FeBr2(THF)(2) afforded (pynac)(2)Fe (1), while treatment of CrCl2(THE)(2), MnCl2, FeBr2(THF)(2), and CoCl(2)py(4) with 2 equiv of (pyEA-(ArPr2)-Pr-i)K afforded pseudotetrahedral (pyEA-(ArPr2)-Pr-i)(2)M (2-M, M = Cr, Mn, Fe) and (pyEA-(ArPr2)-Pr-i)(2)Co-py (2-Co-py). Diamagnetic (kappa-C,N-pyEA-(ArPr2)-Pr-i)(3)Co (3) was prepared in low yield (similar to 7%) from CoCl2, and its Co-C(sp(3)) linkages are unusually low in field strength. Reactivity studies yielded little clean reactivity, but thermolysis of 2-Co-py afforded the bis-indolamide derivative -kappa-N,N-N(C6H3(2-Pr-i)CMe2C(Me)(2-py)}(2)Co (5-Co), and related thermolyses of 2-M (M = Cr, Mn, Fe), conducted on NMA. tube scales, generated related 5-M (M = Cr, Mn, Fe) at roughly the same rates. This observation prompted thermolyses of (pyEA-ArRR')Li, which rearrange to their corresponding indolamides in >90% yields. Rate studies, accompanied by KLE and EIE observations, revealed that an initial hydrogen transfer is reversible and is likely to correspond to an anionic rearrangement, whereas C-C bond formation is rate-determining, as suggested by accompanying calculations. X-ray structure determinations of 1, 2-Fe, 2-Co-py, 3, and 5-Co were conducted.
• US8658802B2
  申请人：——

  公开号：US8658802B2

  公开（公告）日：2014-02-25
• US8933237B2
  申请人：——

  公开号：US8933237B2

  公开（公告）日：2015-01-13
• Anomeric Stereoauxiliary Cleavage of the C−N Bond of <scp>d</scp> ‐Glucosamine for the Preparation of Imidazo[1,5‐a]pyridines
  作者：Kui Zeng、Jin Ye、Xintong Meng、Sebastian Dechert、Martin Simon、Shuaiyu Gong、Ricardo A. Mata、Kai Zhang

  DOI：10.1002/chem.202200648

  日期：2022.5.19

  An α-anomeric stereoauxiliary strategy for the targeted cleavage of C−N bonds in d-glucosamine was achieved through a seven-membered ring transition-state intermediate and the simultaneous incorporation of amine moieties in imidazo[1,5-a]pyridines. This method provides a novel strategy for the C−N bond cleavage and unlocks efficient access to diverse imidazo[1,5-a]pyridines blocks bearing versatile

  通过七元环过渡态中间体和同时在咪唑并[1,5-a]吡啶中掺入胺部分，实现了一种 α-异头立体辅助策略，用于靶向裂解d-氨基葡萄糖中的 C-N 键。该方法为 C-N 键断裂提供了一种新的策略，并解锁了对具有多种官能团的各种咪唑并[1,5-a] 吡啶块的有效访问。