1-(methyl-d₃)-N-(quinolin-8-yl)cyclohexanecarboxamide | 1429896-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(methyl-d₃)-N-(quinolin-8-yl)cyclohexanecarboxamide
• 英文别名: 1-methyl-d3-N-(quinolin-8-yl)cyclohexanecarboxamide；N-quinolin-8-yl-1-(trideuteriomethyl)cyclohexane-1-carboxamide
• CAS: 1429896-65-0
• 化学式: C₁₇H₂₀N₂O
• 分子量: 271.335
• InChiKey: RRBHUZBSORILMF-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(methyl-d₃)-N-(quinolin-8-yl)cyclohexanecarboxamide 、 苯乙炔 在 乙酸-D3 、 sodium acetate 、 nickel diacetate 、 二苯基甲氧基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以6%的产率得到
  参考文献：
  名称：

  Nickel-Catalyzed Stereoselective Alkenylation of C(sp³)–H Bonds with Terminal Alkynes

  摘要：

  A nickel-catalyzed stereoselective alkenylation of an unactivated beta-C(sp(3))-H bond in aliphatic amide with terminal alkynes using 8-aminoquinoline auxiliary is reported for the first time. This reaction displays excellent functional group tolerance with respect to both aliphatic amides and terminal alkynes and features a cheap nickel catalytic system. The 8-aminoquinolyl directing group could be smoothly removed, and the resultant beta-styrylcarboxylic acid derivatives could serve as versatile building blocks for further transformation.

  DOI：

  10.1021/acs.orglett.6b03856
• 作为产物：
  描述：

  环己甲酸甲酯 在 正丁基锂 、 草酰氯 、 水 、 三乙胺 、 二异丙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(methyl-d₃)-N-(quinolin-8-yl)cyclohexanecarboxamide
  参考文献：
  名称：

  Nickel-Catalyzed Addition-Type Alkenylation of Unactivated, Aliphatic C–H Bonds with Alkynes: A Concise Route to Polysubstituted γ-Butyrolactones

  摘要：

  Through the nickel-catalyzed chelation-assisted C-H bond activation strategy, the addition-type -allcenylation of unreactive beta-C(sp(3))-H bonds of aliphatic amides with internal alkynes is developed for the first time to produce gamma/delta-unsaturated carboxylic amide derivatives. The resulting alkenylated products can further be transformed into polysubstituted gamma-butyrolactones with pyridinium chlorochromate (PCC).

  DOI：

  10.1021/acs.orglett.5b01128

文献信息

• Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst
  作者：Jitan Zhang、Hui Chen、Cong Lin、Zhanxiang Liu、Chen Wang、Yuhong Zhang

  DOI：10.1021/jacs.5b07424

  日期：2015.10.14

  A new method of cobalt-catalyzed synthesis of pyrrolidinones from aliphatic amides and terminal alkynes was discovered through a C-H bond functionalization process on unactivated sp(3) carbons with the silver cocatalyst using a bidentate auxiliary. For the first time, a broad range of easily accessible alkynes are exploited as the reaction partner in C(sp(3))-H bond activation to give the important

  通过使用双齿助剂的银助催化剂对未活化的 sp(3) 碳进行 CH 键功能化过程，发现了一种钴催化合成吡咯烷酮从脂肪族酰胺和末端炔烃的新方法。第一次，广泛的易于获得的炔烃被用作 C(sp(3))-H 键活化的反应伙伴，以位点选择性方式提供重要的 5-亚乙基-吡咯烷-2-酮。该反应耐受多种官能团，包括 -F、-Cl、-Br、-CF3、醚、环丙烷和噻吩。吡啶配体和芳香族溶剂都对促进反应性起着重要作用。这种钴催化的环化反应可以成功地扩展到各种芳香酰胺，以提供各种异吲哚啉酮。
• Nickel-Catalyzed Oxidative Coupling of Unactivated C(sp³)–H Bonds in Aliphatic Amides with Terminal Alkynes
  作者：Fei-Xian Luo、Zhi-Chao Cao、Hong-Wei Zhao、Ding Wang、Yun-Fei Zhang、Xing Xu、Zhang-Jie Shi

  DOI：10.1021/acs.organomet.6b00529

  日期：2017.1.9

  In this work, we demonstrated Ni-catalyzed oxidative coupling of unactivated C(sp(3))-H bonds with terminal alkynes for construction of C(sp(3))-C(sp) bonds to synthesize alkyl-substituted internal alkynes. Different amides exhibited good compatibility. Preliminary mechanistic studies were conducted to account for this alkynylation.
• β-Arylation of Carboxamides via Iron-Catalyzed C(sp³)–H Bond Activation
  作者：Rui Shang、Laurean Ilies、Arimasa Matsumoto、Eiichi Nakamura

  DOI：10.1021/ja402806f

  日期：2013.4.24

  A 2,2-disubstituted propionamide bearing an 8-aminoquinolinyl group as the amide moiety can be arylated at the beta-methyl position with an organozinc reagent in the presence of an organic oxidant, a catalytic amount of an iron salt, and a biphosphine ligand at 50 degrees C. Various features of selectivity and reactivity suggest the formation of an organometallic intermediate via rate-determining C-H bond cleavage rather than a free-radical-type reaction pathway.