4-氮杂螺[2.5]辛烷-5-酮 | 546114-04-9

• 物质功能分类: 有机原料 - 螺环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-氮杂螺[2.5]辛烷-5-酮
• 中文别名: 4-氮杂螺[2.5]辛-5-ONE
• 英文名称: 4-azaspiro[2.5]octan-5-one
• 英文别名: 8-azaspiro[2.5]octan-7-one
• CAS: 546114-04-9
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: CPONDIRBUHQHSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  4-氮杂螺[2.5]辛烷-5-酮 在 lithium aluminium tetrahydride 、 硼烷四氢呋喃络合物 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 2-(4-azaspiro[2.5]octan-4-yl)ethanamine
  参考文献：
  名称：

  [EN] PYRAZOLOPYRIMIDINES AND THEIR USES AS PDGFR INHIBITORS
  [FR] PYRAZOLOPYRIMIDINES ET LEURS UTILISATIONS EN TANT QU'INHIBITEURS DE PDGFR

  摘要：

  The disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprising compounds of formula (I), as well as methods of their use and preparation, are also described.

  公开号：

  WO2023007009A1
• 作为产物：
  描述：

  乙基4-氰基丁酸酯 、 乙基溴化镁 在 titanium(IV) isopropylate 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以63%的产率得到4-氮杂螺[2.5]辛烷-5-酮
  参考文献：
  名称：

  Ti-Mediated Chemoselective Conversion of Cyanoesters and Cyanoamides into β-Aminoesters and 1-Aza-spirolactams Bearing a Cyclopropane Ring.

  摘要：

  δ-氰基酯或三级δ-氰基酰胺与格氏试剂和 Ti(i-PrO)4 反应，分别生成带有环丙烷环的δ-氨基酯或酰胺。从 β- 或 γ- 氨基酯开始，通过原位环丙烷化-内酰胺化顺序形成螺环丙内酰胺。

  DOI：

  10.1055/s-2003-36785

文献信息

• Ti-Mediated Chemoselective Conversion of Cyanoesters and Cyanoamides into β-Aminoesters and 1-Aza-spirolactams Bearing a Cyclopropane Ring.
  作者：Jan Szymoniak、Philippe Bertus

  DOI：10.1055/s-2003-36785

  日期：——

  α-Cyanoesters or tertiary α-cyanoamides react with Grignard reagents and Ti(i-PrO)4 to afford respectively β-amino esters or amides, bearing a cyclopropane ring. Starting from β- or γ-cyanoesters, spirocyclopropanelactams are formed via an in situ cyclopropanation-lactamization sequence.

  δ-氰基酯或三级δ-氰基酰胺与格氏试剂和 Ti(i-PrO)4 反应，分别生成带有环丙烷环的δ-氨基酯或酰胺。从 β- 或 γ- 氨基酯开始，通过原位环丙烷化-内酰胺化顺序形成螺环丙内酰胺。
• Palladium-Catalyzed Ring Expansion of Spirocyclopropanes to Form Caprolactams and Azepanes
  作者：Olivier René、Iain A. Stepek、Alberto Gobbi、Benjamin P. Fauber、Simon Gaines

  DOI：10.1021/acs.joc.5b01846

  日期：2015.10.16

  A palladium(0)-catalyzed rearrangement of piperidones and piperidines bearing a spirocyclopropane ring was developed. The ring expansion reaction led to a variety of functionalized caprolactam and azepane products in good to excellent yields. Experimental and computational mechanistic studies revealed an initial oxidative addition of the distal carbon carbon bond of a cyclopropane ring to the palladium(0) catalyst and the relief of ring strain as a driving force for product formation.
• TARGETED DEGRADATION OF VAV1
  申请人：[en]MONTE ROSA THERAPEUTICS, INC.

  公开号：WO2024151547A1

  公开（公告）日：2024-07-18

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt thereof) that degrades Proto-oncogene VAV 1 protein (VAV1). The chemical entities are useful, e.g., for treating a subject (e.g., a human subject) having an inflammatory or autoimmune disorder.
• Studies on the titanium-catalyzed cyclopropanation of nitriles
  作者：Christophe Laroche、Dominique Harakat、Philippe Bertus、Jan Szymoniak

  DOI：10.1039/b508367b

  日期：——

  The Ti-mediated reaction of Grignard reagents with nitriles was investigated with sub-stoichiometric amounts of titanium isopropoxide. Cyanoesters were converted to spirocyclopropanelactams in good yields using as low as 0.05 eq of Ti(OiPr)4. Under similar conditions, cyanocarbonates led to spirocyclopropane oxazolidinones and/or aminocyclopropylcarbinols. A very short synthesis of the naturally occurring aminocyclopropanecarboxylic acid illustrates the usefulness of this methodology.

  用亚化学计量的异丙醇钛研究了格氏试剂与腈的钛介导反应。使用低至 0.05 当量的 Ti(OiPr)4，将氰酯转化为螺环丙内酰胺，收率良好。在类似条件下，氰基碳酸酯产生螺环丙烷恶唑烷酮和/或氨基环丙基甲醇。天然存在的氨基环丙烷甲酸的非常简短的合成说明了该方法的有用性。
• [EN] PYRAZOLOPYRIMIDINES AND THEIR USES AS PDGFR INHIBITORS<br/>[FR] PYRAZOLOPYRIMIDINES ET LEURS UTILISATIONS EN TANT QU'INHIBITEURS DE PDGFR
  申请人：[en]ACTELION PHARMACEUTICALS LTD

  公开号：WO2023007009A1

  公开（公告）日：2023-02-02

  The disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprising compounds of formula (I), as well as methods of their use and preparation, are also described.