4-甲基-1-戊烯-3-酮 | 1606-47-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲基-1-戊烯-3-酮
• 英文名称: isopropyl vinyl ketone
• 英文别名: Isopropylvinylketon；4-methylpent-1-en-3-one；4-methyl-1-penten-3-one；4-Methyl-pent-1-en-3-on；3-oxo-4-methyl-1-pentene
• CAS: 1606-47-9
• 化学式: C₆H₁₀O
• mdl: MFCD00129062
• 分子量: 98.1448
• InChiKey: SNOYUTZWILESAI-UHFFFAOYSA-N

物化性质

• 沸点：
  50 °C(Press: 90 Torr)
• 密度：
  0.837 g/cm3
• 保留指数：
  830
• 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)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• 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

安全信息

• 海关编码：
  2914190090

反应信息

• 作为反应物：
  描述：

  4-甲基-1-戊烯-3-酮 在 吡啶 、 2-(2-hydroxyethyl)-3-methyl-4-benzylthiazolium chloride 、 溶剂黄146 、 三乙胺 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 3-[2-(4-Fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-butyronitrile
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 1. trans-6-(2-Pyrrol-1-ylethyl)-4-hydroxypyran-2-ones, a novel series of HMG-CoA reductase inhibitors. 1. Effects of structural modifications at the 2- and 5-positions of the pyrrole nucleus

  摘要：

  A novel series of trans-6-(2-pyrrol-1-ylethyl)-4-hydroxypyran-2-ones and their dihydroxy acid derivatives were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. A systematic study of substitution at the 2- and 5-positions of the pyrrole ring revealed that optimum potency was realized with the 2-(4-fluorophenyl)-5-isopropyl derivative 8x, which possessed 30% of the in vitro activity of the potent fungal metabolite compactin (I). A molecular modeling analysis led to the description of a pharmacophore model characterized by (A) length limits of 5.9 and 3.3 A for the 2- and 5-substituents, respectively, as well as an overall width limit of 10.6 A across the pyrrole ring from the 2- to the 5-substituent and (B) an orientation of the ethyl(ene) bridge to the 4-hydroxypyran-2-one ring nearly perpendicular to the planes of the parent pyrrole, hexahydronaphthalene, and phenyl rings of the structures examined (Figure 3, theta = 80-110 degrees). Attempts to more closely mimic compactin's polar isobutyric ester side chain with the synthesis of 2-phenylpyrroles containing polar phenyl substituents resulted in analogues with equal or slightly reduced potencies when compared to the 2-[(unsubstituted or 4-fluoro)phenyl]pyrroles, supporting the hypothesis that inhibitory potency is relatively insensitive to side-chain polarity or charge distribution in this area.

  DOI：

  10.1021/jm00163a005
• 作为产物：
  描述：

  顺式-4-甲基-2-戊烯 在 吡啶 、 4-二甲氨基吡啶 、 5,10,15,20-tetrakisphenylporphyrin 、 氧气 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以58%的产率得到4-甲基-1-戊烯-3-酮
  参考文献：
  名称：

  A one-pot conversion of olefins to .alpha.,.beta.-unsaturated carbonyl compounds. An easy synthesis of 2-cyclopentenone and related compounds

  摘要：

  DOI：

  10.1021/jo00170a060

文献信息

• Design and Enantioselective Synthesis of Cashmeran Odorants by Using “Enol Catalysis”
  作者：Irene Felker、Gabriele Pupo、Philip Kraft、Benjamin List

  DOI：10.1002/anie.201409591

  日期：2015.2.2

  syntheses involve a novel asymmetric Brønsted acid catalyzed Michael addition of unactivated α‐substituted ketones. This key transformation was realized by utilizing a new type of enol activation catalysis and affords different cyclic ketones bearing α‐quaternary stereocenters in good to excellent yields and with high enantioselectivity. Subsequent McMurry coupling and Saegusa–Ito oxidation furnished

  通过分子模型设计了新颖的Cashmeran增香剂。他们的简短合成涉及一种新的不对称布朗斯台德酸催化未活化的α-取代的酮的迈克尔加成反应。这种关键的转变是通过利用新型的烯醇活化催化来实现的，并提供了具有α-季立体中心的不同环状酮，产率高至优异，对映选择性高。随后的McMurry偶联和Saegusa-Ito氧化提供了对映纯目标气味，其中一种对映异构体确实具有Cashmeran的典型嗅觉特性。
• Synthesis of Fluoroalkyl Pyrazoles from In-Situ-Generated C₂F₅CHN₂and Electron-Deficient Alkenes
  作者：Pavel K. Mykhailiuk、Aleksandr Yu. Ishchenko、Viatcheslav Stepanenko、Janine Cossy

  DOI：10.1002/ejoc.201600947

  日期：2016.11

  C2F5-substituted pyrazolines were synthesized by [3+2]-cycloaddition between in-situ-generated C2F5CHN2 and electron-deficient alkenes. The addition of DBU led to the elimination of HF to give CF3CHF-substituted pyrazoles. Depending on the structure of the pyrazolines, different products were obtained.

  C2F5 取代的吡唑啉是通过原位生成的 C2F5CHN2 和缺电子烯烃之间的 [3+2]-环加成合成的。DBU 的加入导致 HF 的消除，得到 CF3CHF 取代的吡唑。根据吡唑啉的结构，获得不同的产物。
• Ruthenium–Lewis Acid Catalyzed Asymmetric Diels–Alder Reactions between Dienes and α,β-Unsaturated Ketones
  作者：Jenny Rickerby、Martial Vallet、Gerald Bernardinelli、Florian Viton、E. Peter Kündig

  DOI：10.1002/chem.200600851

  日期：2007.4.16

  The complex [Ru(Cp)(R,R-BIPHOP-F)(acetone)][SbF(6)], (R,R)-1 a, was used as catalyst for asymmetric Diels-Alder reactions between dienes (cyclopentadiene, methylcyclopentadiene, isoprene, 2,3-dimethylbutadiene) and alpha,beta-unsaturated ketones (methyl vinyl ketone (MVK), ethyl vinyl ketone, divinyl ketone, alpha-bromovinyl methyl ketone and alpha-chlorovinyl methyl ketone). The cycloaddition products

  络合物[Ru（Cp）（R，R-BIPHOP-F）（丙酮）] [SbF（6）]，（R，R）-1 a被用作二烯（环戊二烯）之间不对称Diels-Alder反应的催化剂，甲基环戊二烯，异戊二烯，2,3-二甲基丁二烯）和α，β-不饱和酮（甲基乙烯基酮（MVK），乙基乙烯基酮，二乙烯基酮，α-溴乙烯基甲基酮和α-氯乙烯基甲基酮）。获得环加成产物，产率为50-90％，对映选择性高达96％ee。乙基乙烯基酮，二乙烯基酮和卤代乙烯基酮效果最好，它们与无环二烯的反应始终为ee提供90％以上的产品。α-氯代乙烯基乙烯基酮的性能优于α-溴乙烯基甲基酮。该反应还通过分子内环加成反应在95％ee中提供了[4.3.1]双环系统。
• [EN] 2,3-BENZOXAZIN DERIVATIVES AS NON-STEROIDAL GLUCOCORTICOID RECEPTOR MODULATORS<br/>[FR] DERIVES DE 2,3-BENZOXAZINE UTILISES EN TANT QUE MODULATEURS NON STEROIDIENS DU RECEPTEUR GLUCOCORTICOIDE
  申请人：GLAXO GROUP LTD

  公开号：WO2006000398A1

  公开（公告）日：2006-01-05

  The present invention provides compounds of formula (I), wherein R1 represents 1-ethylpropyl, 1-methylethyl or 2-methylpropyl; 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.

  本发明提供了式(I)的化合物，其中R1代表1-乙基丙基、1-甲基乙基或2-甲基丙基；或其生理功能衍生物；包括这些化合物的药物组合物，这些化合物用于制造药物，特别用于治疗炎症和/或过敏症状，以及用于制备这些化合物的过程和制造这些化合物的化学中间体。
• Synthesis of 3-Methylenecyclohexan-1-ols by Lewis Acid Catalyzed Cyclization of (Epoxy-allyl)silanes
  作者：Francisco J. Pulido、Asunción Barbero、Pilar Castreño

  DOI：10.1002/ejoc.200901263

  日期：2010.3

  A new route for the synthesis of (epoxy-allyl)silanes bearing the PhMe 2 Si group has been developed and their acid-catalyzed cyclization studied. The so-called normal products derived from 5-exo or 6-endo attack were never obtained. On the contrary, an interesting tandem rearrangement/cyclization process was observed, which selectively led to 3-methylenecyclohexan-1-ols. A mechanism is proposed to

  已经开发了一种合成带有 PhMe 2 Si 基团的（环氧-烯丙基）硅烷的新途径，并研究了它们的酸催化环化。5-exo 或 6-endo 攻击衍生的所谓正常产物从未得到过。相反，观察到了一个有趣的串联重排/环化过程，它选择性地产生了 3-亚甲基环己-1-醇。提出了一种机制来解释这种串联反应。环化过程的立体选择性取决于催化剂的性质。

表征谱图