1-环丙基丙-2-烯-1-酮 | 59819-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-环丙基丙-2-烯-1-酮
• 中文别名: 1-环丙基-2-丙烯酮
• 英文名称: cyclopropyl vinyl ketone
• 英文别名: 1-cyclopropylprop-2-en-1-one；Cyclopropylvinylketon；1-Cyclopropyl-2-propen-1-one
• CAS: 59819-62-4
• 化学式: C₆H₈O
• mdl: MFCD18975090
• 分子量: 96.1289
• InChiKey: TWFKEGONKTUVSX-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 60 Torr)
• 密度：
  1.000±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-环丙基丙-2-烯-1-酮 在 正丁基锂 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成
  参考文献：
  名称：

  Dissociated Nonsteroidal Glucocorticoid Receptor Modulators; Discovery of the Agonist Trigger in a Tetrahydronaphthalene−Benzoxazine Series

  摘要：

  The tetrahydronaphthalene-benzoxazine glucocorticoid receptor (GR) partial agonist 4b was optimized to produce potent full agonists of GR. Aromatic ring substitution of the tetrahydronaphthalene leads to weak GR antagonists. Discovery of an "agonist trigger" substituent on the saturated ring of the tetrahydronaphthalene leads to increased potency and efficacious GR agonism. These compounds are efficacy selective in an NFkB GR agonist assay ( representing transrepression effects) over an MMTV GR agonist assay ( representing transactivation effects). 52 and 60 have NFkB pIC(50) = 8.92 (105%) and 8.69 (92%) and MMTV pEC(50) = 8.20 (47%) and 7.75 (39%), respectively. The impact of the trigger substituent on agonism is modeled within GR and discussed. 36, 52, and 60 have anti-inflammatory activity in a mouse model of inflammation after topical dosing with 52 and 60, having an effect similar to that of dexamethasone. The original lead was discovered by a manual agreement docking method, and automation of this method is also described.

  DOI：

  10.1021/jm060302x
• 作为产物：
  描述：

  1-trimethylsilyloxy-1,1'-bicyclopropyl 在 四甲基乙二胺 、 四氯化锡 作用下， 生成 1-环丙基丙-2-烯-1-酮
  参考文献：
  名称：

  .beta.-Trichlorostannyl ketones and aldehydes. Preparation and facile amine-induced dehydrostannation leading to .alpha.-methylene ketones and aldehydes

  摘要：

  Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give beta-trichlorostannyl ketones and aldehydes 3 in high yields. The beta-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding alpha-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N',N'-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to alpha-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The H-1 NMR, C-13 NMR, Sn-119 NMR, and IR spectral properties of beta-stannyl ketones and aldehydes are also reported.

  DOI：

  10.1021/jo00027a008

文献信息

• Electrooxidative Coupling of Furans and Silyl Enol Ethers:  Application to the Synthesis of Annulated Furans
  作者：Jeffrey B. Sperry、Christopher R. Whitehead、Ion Ghiviriga、Ryan M. Walczak、Dennis L. Wright

  DOI：10.1021/jo049889i

  日期：2004.5.1

  The preparation of annulated furan systems as key synthetic intermediates through the application of a two-step annulation involving an electrochemical ring closure between a furan and a silyl enol ether has been studied. The reaction was shown to be quite general for the formation of six-membered rings in good yields and was tolerant of a variety of different functional groups. The ring closure was

  已经研究了通过在呋喃和甲硅烷基烯醇醚之间进行电化学闭环的两步环化法制备作为主要合成中间体的环呋喃体系。对于六元环的形成，以高产率形成该反应是相当普遍的，并且耐受各种不同的官能团。闭环是高度立体选择性的，导致形成顺式融合系统。循环伏安法和探针分子可用于深入了解反应。这些研究表明，关键环的闭合涉及甲硅烷基烯醇醚的初始氧化为自由基阳离子，然后呋喃终止的环化。
• The friedel-crafts reaction of acid chlorides with ethene ; Di-addition and molecular rearrangement
  作者：Francis X Bates、John A Donnelly、John R Keegan

  DOI：10.1016/s0040-4020(01)80962-5

  日期：1991.1

  Acid chlorides, complexed with excess aluminium chloride, reacted with ethene to form 3-methyl-2-buten-1-ones, i.e. rearranged di-addition products having a terminal isoprenoid skeleton, together with the usual β-chloropropanones. The latter were the sole products in the absence of excess catalyst. Acid chlorides containing a suitably situated π-system underwent intramolecular cyclization, e.g. 2-

  酰氯与过量的氯化铝络合，与乙烯反应形成3-甲基-2-丁烯-1-酮，即具有末端类异戊二烯骨架的重排二加成产物，以及通常的β-氯丙烷。后者是在没有过量催化剂的情况下的唯一产物。含有适当位置的π系统的酰氯进行了分子内环化，例如将2-苯基环丙烷羰基氯（10）环化为3,4-苯并双环[3.1.0]己-2-酮（11）。
• Synthesis of <i>N</i> -Nitroso CHF₂ -Pyrazolines and Their Transformation into CHF₂ -Isoxazolines and -Pyrazoles
  作者：Pavlo S. Lebed、Johan Fenneteau、Yong Wu、Janine Cossy、Pavel K. Mykhailiuk

  DOI：10.1002/ejoc.201700803

  日期：2017.11.9

  N-Nitroso CHF2-pyrazolines were synthesized from in situ generated difluoromethyldiazomethane (CF2HCHN2), tert-butyl isonitrite (tBuONO), and alkenes. The synthesis of representative CHF2-pyrazoles and CHF2-oxazolines was also performed.

  N-亚硝基 CHF2-吡唑啉由原位生成的二氟甲基重氮甲烷 (CF2HCHN2)、叔丁基异腈 (tBuONO) 和烯烃合成。还进行了代表性 -吡唑和 -恶唑啉的合成。
• Anti acid-fast bacterial agent containing pyridonecarboxylic acids as active ingredient
  申请人：——

  公开号：US20030119848A1

  公开（公告）日：2003-06-26

  1 Anti-acid-fast bacterial agents containing as the active ingredient compounds represented by the general formula (1), salts thereof or hydrates of the same. Namely, pyridonecarboxylic acid derivatives having an excellent antibacterial activity on tubercle bacillus and a typical acid-fast bacteria, favorable kinetics in vivo and a high safety.

  抗酸快细菌药剂包含以一般式（1）表示的化合物作为活性成分，其盐或水合物。即，对结核杆菌和典型酸快细菌具有出色抗菌活性、在体内具有良好的动力学特性和高安全性的吡啶酮羧酸衍生物。
• [EN] SUBSTITUTED OXAZINES AS GLUCOCORTICOID RECEPTOR MODULATORS<br/>[FR] OXAZINES SUBSTITUEES UTILISEES COMME MODULATEURS DU RECEPTEUR GLUCOCORTICOIDE
  申请人：GLAXO GROUP LTD

  公开号：WO2006000401A1

  公开（公告）日：2006-01-05

  The present invention is directed to compounds of formula (I), wherein R1 represents a C3-6cycloalkyl group; or a physiologically functional derivative thereof, pharmaceutical compositions comprising the compounds, the use of the compounds for the manufacture of medicaments particularly for the treatment of inflammatory and/or allergic conditions, processes for the preparation of the compounds, and chemical intermediates in the processes for the manufacture of the compounds.

  本发明涉及以下式（I）化合物，其中R1代表C3-6环烷基基团；或其生理功能衍生物，包括该化合物的药物组合物，该化合物用于制造特别用于治疗炎症和/或过敏症的药物，该化合物的制备方法，以及用于制造该化合物的过程中的化学中间体。