双环[4.1.0]庚烷-4-酮 | 60582-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 双环[4.1.0]庚烷-4-酮
• 英文名称: bicyclo[4.1.0]heptan-3-one
• 英文别名: 3-norcaranone
• CAS: 60582-64-1
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: FNSLUWUWXKOLFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  双环[4.1.0]庚烷-4-酮 在 lithium hydroxide monohydrate 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 1,4,4a,5,5a,6-hexahydrocyclopropa[f]indazole-3-carboxylic acid
  参考文献：
  名称：

  Property- and Structure-Guided Discovery of a Tetrahydroindazole Series of Interleukin-2 Inducible T-Cell Kinase Inhibitors

  摘要：

  Interleukin-2 inducible T-cell kinase (ITK), a member of the Tec family of tyrosine kinases, plays a major role in T-cell signaling downstream of the T-cell receptor (TCR), and considerable efforts have been directed toward discovery of ITK-selective inhibitors as potential treatments of inflammatory disorders such as asthma. Using a previously disclosed indazole series of inhibitors as a starting point, and using X-ray crystallography and solubility forecast index (SFI) as guides, we evolved a series of tetrahydroindazole inhibitors with improved potency, selectivity, and pharmaceutical properties. Highlights include identification of a selectivity pocket above the ligand plane, and identification of appropriate lipophilic substituents to occupy this space. This effort culminated in identification of a potent and selective ITK inhibitor (GNE-9822) with good ADME properties in preclinical species.

  DOI：

  10.1021/jm500550e
• 作为产物：
  描述：

  3-cyclohexen-1-ol 在 chromium(VI) oxide 、 铜 、 锌 作用下， 生成 双环[4.1.0]庚烷-4-酮
  参考文献：
  名称：

  Relative rates and stereochemistry of the iodomethylzinc iodide methylenation of some hydroxy- and methoxy-substituted cyclic olefins

  摘要：

  DOI：

  10.1021/ja01025a028

文献信息

• [EN] PYRAZOLE CARBOXAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS PYRAZOLE CARBOXAMIDES, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014023258A1

  公开（公告）日：2014-02-13

  Provided herein are compounds of formula (AA): N N H HN O N N R R 6 A (R a ) p, (AA) stereoisomers or a pharmaceutically acceptable salt thereof, wherein A, R a, p, R and R 6 are defined herein, compositions including the compounds and methods of manufacturing and using the compounds for the treatment of diseases.

  本文提供了以下式（AA）的化合物：N N H HN O N N R R 6 A（R a）p，（AA）立体异构体或其药学上可接受的盐，其中A、R a、p、R和R 6在此处有定义，包括这些化合物的组合物以及用于治疗疾病的制备和使用这些化合物的方法。
• Products from Enzyme-Catalyzed Oxidations of Norcarenes
  作者：Martin Newcomb、Dharmika S. P. Lansakara-P.、Hye-Yeong Kim、R. Esala P. Chandrasena、Stephen J. Lippard、Laurance G. Beauvais、Leslie J. Murray、Viviana Izzo、Paul F. Hollenberg、Minor J. Coon

  DOI：10.1021/jo061865j

  日期：2007.2.1

  Recent studies revealed that norcarane (bicyclo[4.1.0]heptane) is oxidized to 2-norcarene (bicyclo[4.1.0]-hept-2-ene) and 3-norcarene (bicyclo[4.1.0]hept-3-ene) by iron-containing enzymes and that secondary oxidation products from the norcarenes complicate mechanistic probe studies employing norcarane as the substrate (Newcomb, M.; Chandrasena, R. E. P.; Lansakara-P., D. S. P.; Kim, H.-Y.; Lippard

  最近的研究表明，正戊烷（双环[4.1.0]庚烷）被氧化为2-降冰片烯（双环[4.1.0]-庚-2-烯）和3-降冰片烯（双环[4.1.0]庚烯-3-烯） ）和含正铁烷的次级氧化产物使以正二十烷为底物的机械探针研究复杂化（Newcomb，M .; Chandrasena，REP; Lansakara-P。，DSP; Kim，H.-Y .; Lippard， SJ;博韦，LG;默里，LJ;伊佐，V。; Hollenberg，PF;浣熊，MJ有机化学杂志。2007年，72，1121-1127）。在目前的工作中，确定了由几种酶氧化2-降冰片烯和3-降冰片烯的产物分布。大多数产品是通过GC和GC-质谱与独立生产的真实样品进行比较而鉴定的。在某些情况下，通过产物的2D NMR分析确定或确认了立体化学分配。在该工作中研究的酶是4种细胞色素P450酶，CYP2B1，CYPΔ2E1，CYPΔ2E1T303A，
• Bridged spiropentanes: Ring expansion
  作者：Kenneth B. Wiberg、John R. Snoonian

  DOI：10.1016/0040-4039(94)02489-x

  日期：1995.2

  Diazomethane ring expansion of tricyclo[4.1.0.01,3]heptan-4-one provides a convenient route to three carbon-bridged spiropentanes. The relative rates of reaction and the migratory preferences of cyclopropyl vs methylene were examined for several cyclopropyl alkyl ketones, and were correlated with the results of HF/6-31G∗ MO calculations.

  三环[4.1.0.0 1,3 ]庚烷-4-酮的重氮甲烷环扩环提供了通往三个碳桥联螺环戊烷的便捷途径。研究了几种环丙基烷基酮的相对反应速率以及环丙基与亚甲基的迁移偏好，并将其与HF / 6-31G * MO计算结果相关联。
• PYRAZOLE CARBOXAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：Genentech, Inc.

  公开号：US20150158851A1

  公开（公告）日：2015-06-11

  Provided herein are compounds of formula (AA): stereoisomers or a pharmaceutically acceptable salt thereof, wherein A, R a , p, R 5 and R 6 are defined herein, compositions including the compounds and methods of manufacturing and using the compounds for the treatment of diseases.

  本文提供了式（AA）的化合物：其立体异构体或其药学上可接受的盐，其中A、Ra、p、R5和R6在此定义，包括该化合物的组合物以及制造和使用该化合物治疗疾病的方法。
• Cage Escape Competes with Geminate Recombination during Alkane Hydroxylation by the Diiron Oxygenase AlkB
  作者：Rachel N. Austin、Kate Luddy、Karla Erickson、Marilla Pender‐Cudlip、Erin Bertrand、Dayi Deng、Ryan S. Buzdygon、Jan B. van Beilen、John T. Groves

  DOI：10.1002/anie.200801184

  日期：2008.6.27

  Three structurally analogous radical clock substrates with a 100-fold span in their rearrangement rates are hydroxylated by the diiron oxygenase AlkB to afford similar amounts of rearranged and unrearranged products. Such a result is predicted by a mechanistic scheme by which radical rebound competes with cage escape of the geminate substrate radical. The results show that radical clocks can measure both the radical life-time and the kinetics of cage escape.