cyclobutyl(piperidin-1-yl)methanone | 15911-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: cyclobutyl(piperidin-1-yl)methanone
• 英文别名: 1-(cyclobutylcarbonyl)piperidine
• CAS: 15911-03-2
• 化学式: C₁₀H₁₇NO
• mdl: MFCD13506895
• 分子量: 167.251
• InChiKey: ZSKKKXWEJSZUBT-UHFFFAOYSA-N

物化性质

• 沸点：
  297.6±9.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cyclobutyl(piperidin-1-yl)methanone 在 2,4,6-三甲基吡啶 、 三氟甲磺酸酐 、 (-)-diisopinocamphenylborane chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 26.75h， 生成 (5S,10S)-(+)-trispiro[3.0.0.3.2.2]tridecan-10-ol
  参考文献：
  名称：

  A new approach to helical primary structures of four-membered rings: (P)- and (M)-tetraspiro[3.0.0.0.3.2.2.2]hexadecane

  摘要：

  A new approach to helical primary structures of four-membered rings uses a cycloaddition of a trimethylenketeniminium salt to suitable tailored methylenecyclobutanes to assemble the desired carbon framework. The results are short and effective syntheses of (M)-trispiro[3.0.0.3.2.2]tridecane [(M-5], and (P)- and (M)-tetraspiro[3.0.0.0.3.2.2.2]hexadecane [(P)- and (M)-24]. Unlike helices of three-membered rings, the specific rotation decreases, as the length of the helix increases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.081
• 作为产物：
  描述：

  哌啶 、 环丁基甲酰氯 以 二氯甲烷 为溶剂， 反应 0.5h， 以97%的产率得到cyclobutyl(piperidin-1-yl)methanone
  参考文献：
  名称：

  A new approach to helical primary structures of four-membered rings: (P)- and (M)-tetraspiro[3.0.0.0.3.2.2.2]hexadecane

  摘要：

  A new approach to helical primary structures of four-membered rings uses a cycloaddition of a trimethylenketeniminium salt to suitable tailored methylenecyclobutanes to assemble the desired carbon framework. The results are short and effective syntheses of (M)-trispiro[3.0.0.3.2.2]tridecane [(M-5], and (P)- and (M)-tetraspiro[3.0.0.0.3.2.2.2]hexadecane [(P)- and (M)-24]. Unlike helices of three-membered rings, the specific rotation decreases, as the length of the helix increases. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.081

文献信息

• TNF -Alpha Modulating Benzimidazoles
  申请人：UCB Biopharma SPRL

  公开号：US20150152065A1

  公开（公告）日：2015-06-04

  A series of benzimidazole derivatives, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

  一系列苯并咪唑衍生物，作为人类肿瘤坏死因子α活性的强效调节剂，因此在治疗和/或预防各种人类疾病方面具有益处，包括自身免疫和炎症性疾病；神经和神经退行性疾病；疼痛和痛觉障碍；心血管疾病；代谢性疾病；眼科疾病；以及肿瘤学疾病。
• Imidazopyrazine Derivatives as Modulators of TNF Activity
  申请人：UCB Biopharma SPRL

  公开号：US20150191482A1

  公开（公告）日：2015-07-09

  A series of imidazo[1,2-α]pyrazine derivatives, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorder; and oncological disorders.

  一系列咪唑并[1,2-α]吡嗪衍生物，作为强效的人类TNFα活性调节剂，因此在治疗和/或预防各种人类疾病方面具有益处，包括自身免疫和炎症性疾病；神经学和神经退行性疾病；疼痛和伤害感知性疾病；心血管疾病；代谢性疾病；眼部疾病；以及肿瘤学疾病。
• [EN] IMIDAZOPYRAZINE DERIVATIVES AS MODULATORS OF TNF ACTIVITY<br/>[FR] DÉRIVÉS D'IMIDAZOPYRAZINE EN TANT QUE MODULATEURS DE L'ACTIVITÉ TNF
  申请人：UCB PHARMA SA

  公开号：WO2014009296A1

  公开（公告）日：2014-01-16

  A series of imidazo[1,2-α]pyrazine derivatives, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

  一系列咪唑并[1,2-α]吡嗪衍生物，作为强效的人类TNFα活性调节剂，因此在治疗和/或预防各种人类疾病方面具有益处，包括自身免疫和炎症性疾病；神经和神经退行性疾病；疼痛和伤害感知性疾病；心血管疾病；代谢性疾病；眼部疾病；以及肿瘤性疾病。
• Pd(II)-Catalyzed Enantioselective C(sp³)–H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines
  作者：Jesus Rodrigalvarez、Luke A. Reeve、Javier Miró、Matthew J. Gaunt

  DOI：10.1021/jacs.1c11921

  日期：2022.3.9

  simple N-acetyl amino acid ligand, which not only controls the enantioselectivity but also promotes γ-C–H activation of over other pathways. Computational analysis of the cyclopalladation step provides an understanding of how enantioselective C–H cleavage occurs and revealed distinct transition structures to our previous work on enantioselective desymmetrization of N-isobutyl tertiary alkylamines. This

  应变氨甲基环烷烃是药物化学中经常出现的支架，因为它们具有独特的结构特征，可产生一系列生物学特性。在这里，我们报道了钯催化的氨甲基环丙烷和环丁烷与芳基硼酸的对映选择性 C(sp 3 )-H 芳基化反应。一系列天然叔烷基胺基团能够指导 C-H 裂解并在应变环烷烃骨架上形成碳-芳基键作为单一非对映异构体并具有出色的对映异构体比率。该策略成功的核心是使用简单的N-乙酰氨基酸配体，不仅控制对映选择性，而且促进 γ-C-H 活化超过其他途径。环钯化步骤的计算分析提供了对对映选择性 C-H 裂解如何发生的理解，并揭示了我们之前关于N-异丁基叔烷基胺的对映选择性去对称化的不同过渡结构。这种直接且操作简单的方法简化了官能化氨甲基应变环烷烃的构建，我们相信这将在与生物活性小分子合成相关的学术和工业环境中得到广泛应用。
• Synthesis of Highly Substituted Cyclobutanones by a One‐Pot Keteniminium‐Enamine Process
  作者：Dylan Dagoneau、Amandine Kolleth、Pierre Quinodoz、Beyza Horoz、Saron Catak、Alexandre Lumbroso、Sarah Sulzer‐Mossé、Alain De Mesmaeker

  DOI：10.1002/hlca.202100022

  日期：2021.5

  synthesis of highly substituted cyclobutanones. This process relies on first a [2+2] cycloaddition involving a keteniminium salt intermediate with an alkene followed by isomerization of the resulting cyclobutaniminium salt into its cyclic enamine form and then reaction of the latter with an electrophile. The adduct can be either hydrolyzed or reduced to give the corresponding cyclobutanone or cyclobutanamine

  在本文中，我们描述了有效的一锅序列，用于高度取代的环丁酮的区域和立体选择性合成。该方法首先依赖于[2 + 2]环加成反应，该加成反应包括将烯酮铵盐中间体与烯键合，然后将所得的环丁铵盐异构化成其环状烯胺形式，然后使后者与亲电子试剂反应。可以将加合物水解或还原，分别得到相应的环丁酮或环丁胺，并具有出色的非对映异构控制能力。容许多种亲电试剂，从而允许将各种取代基和官能团结合到环丁基环上。此外，通过DFT研究研究了各种环烯胺的共面性。