4-异丙基环己-2-烯-1-酮 | 500-02-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-异丙基环己-2-烯-1-酮
• 中文别名: 4-异丙基-2-环己基烯酮；4-(1-甲基乙基)-2-环己烯-1-酮
• 英文名称: cryptone
• 英文别名: crypton；4-isopropyl-2-cyclohexenone；(±)-cryptone；4-isopropyl-2-cyclohexen-1-one；4-isopropylcyclohex-2-enone；4-(1-methylethyl)-cyclohex-2-en-1-one；4-(1-methylethyl)-2-cyclohexen-1-one；4-isopropylcyclohex-2-en-1-one；4-propan-2-ylcyclohex-2-en-1-one
• CAS: 500-02-7
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: AANMVENRNJYEMK-UHFFFAOYSA-N

物化性质

• 沸点：
  98-100 °C(Press: 10 Torr)
• 密度：
  0.9472-0.9483 g/cm3(Temp: 15 °C)
• 溶解度：
  氯仿（微溶）、乙醇（微溶）、乙酸乙酯（微溶）
• LogP：
  1.82
• 物理描述：
  Colourless liquid; woody minty herbaceous
• 折光率：
  1.481-1.490
• 保留指数：
  1153;1156;1157;1169;1148;1157;1156;1150;1148;1165;1150;1148;1159;1159;1160;1160;1146;1158;1160;1152;1167;1155;1163;1140;1156;1165;1160;1159;1148;1151;1165;1159;1165;1165;1165;1161
• 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)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

制备方法与用途

制备方法

由1-(1-六氢吡啶)-3-甲基-1-丁烯制备。

合成制备方法

同样是由1-(1-六氢吡啶)-3-甲基-1-丁烯制备。

用途简介

（暂无内容）

反应信息

• 作为反应物：
  描述：

  4-异丙基环己-2-烯-1-酮 在 溴 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 以92%的产率得到2-bromo-4-isopropylcyclohex-2-enone
  参考文献：
  名称：

  Intramolecularly Competitive Ireland-Claisen Rearrangements:  Scope and Potential Applications to Natural Product Synthesis

  摘要：

  A variety of bis-allylic esters were prepared by vinylmetal addition to cycloalkenones followed by esterification either in situ or in a separate operation. For chiral cyclohexenones, the vinyl additions generally occurred with > 10:1 diastereoselectivity. Although in some cases the bis-allylic esters proved to be sensitive to silica gel or other adsorbents, all of the esters examined could be isolated in acceptable purity. The Ireland-Claisen rearrangement of the bis-allylic esters occurred with complete regioselectivity via the exocyclic alkene. The alkene stereochemistry and the stereochemistry at C-2 and C-3 of the pentenoic acid products were consistent with a chairlike transition state in the rearrangement. Substituents at the carbons adjacent to the allylic carbinol carbon (i.e., C-2 or C-6 in cyclohexenone-derived substrates) directed the stereochemical course of the rearrangement. The rearrangements generally proceeded so as to place the larger of the C-2 or C-6 substituents in the pseudoequatorial position with respect to the chairlike transition state. For a bis-allylic ester bearing both a C-2-CH3 and a C-6-OMEM substituent, the rearrangement product resulted from the nominally smaller OMEM substituent occupying a pseudoequatorial position with respect to the chairlike transition state.

  DOI：

  10.1021/jo010752r
• 作为产物：
  描述：

  (+/-)-4-isopropyl-2-phenylselenenylcyclohexanone 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以31%的产率得到4-异丙基环己-2-烯-1-酮
  参考文献：
  名称：

  Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers

  摘要：

  (S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (+/-)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.030

文献信息

• Lewis Acid Activation of Fragment-Coupling Reactions of Tertiary Carbon Radicals Promoted by Visible-Light Irradiation of EDA Complexes
  作者：Spencer P. Pitre、Tyler K. Allred、Larry E. Overman

  DOI：10.1021/acs.orglett.1c00023

  日期：2021.2.5

  The addition of tertiary carbon radicals generated from N-(acyloxy)phthalimide esters to cyclic α,β-unsaturated ketones and lactones is markedly enhanced by the addition of substoichiometric amounts of a Ln(OTf)3. The reaction is accomplished by irradiation with visible light in the absence of a photosensitizer and is suggested to proceed by excitation of a ternary electron donor–acceptor complex between

  通过添加亚化学计量的Ln（OTf）3，可以显着增强将N-（酰氧基）邻苯二甲酰亚胺酯生成的叔碳基团加到环状α，β-不饱和酮和内酯上。该反应通过在不存在光敏剂的情况下用可见光照射完成，并建议通过在NHPI酯，Hantzsch酯和Ln（OTf）3之间激发三元电子供体-受体配合物来进行。
• Ultrasonically improved reductive properties of an aqueous ZnNiCl2 system-1 selective reduction of α,β-unsaturated carbonyl compounds
  作者：Christian Petrier、Jean-Louis Luche

  DOI：10.1016/s0040-4039(00)96120-3

  日期：——

  Conjugate hydrogenation of several compounds is obtained with good to excellent yield in an aqueous medium using a reagent constituted by zinc dust and nickel chloride(9–1). ultrasounds are shown to improve the yields and reaction rates.

  使用由锌粉和氯化镍构成的试剂，可以在水性介质中以良好至极好的收率对几种化合物进行共轭氢化（9-1）。超声波可以提高产量和反应速度。
• Chemical synthons and intermediates
  申请人：——

  公开号：US20040138485A1

  公开（公告）日：2004-07-15

  The invention provides novel six and seven-carbon termini-differentiated polypropionate stereotetrads and stereopentads useful in syntheses of natural products. The invention also provides a novel alkylative sulfenylation-desulfonylation process that efficiently transforms enantiopure epoxyvinyl sulfones to syn and anti dienylsulfides in two operations.

  这项发明提供了新颖的六碳和七碳末端差异化的聚丙酸酯立体四聚体和立体五聚体，可用于合成天然产物。该发明还提供了一种新颖的烷基化磺化-去磺化过程，能够高效地将对映纯环氧乙烯基磺酮转化为syn和anti二烯基硫醚，只需两步操作。
• Copper Hydride-Catalyzed Tandem 1,4-Reduction/Alkylation Reactions
  作者：Bruce H. Lipshutz、Will Chrisman、Kevin Noson、Patrick Papa、Joseph A. Sclafani、Randall W. Vivian、John M. Keith

  DOI：10.1016/s0040-4020(00)00132-0

  日期：2000.4

  Exposure of an enone to a catalytic quantity of [CuH(PPh3)]6 in the presence of one of several silyl hydrides (PhMe2SiH, PMHS, HMe2SiOSiMe2H) leads to conjugate reduction with concomitant formation of the corresponding silyl enol ether. Without isolation, treatment of these intermediates with a Lewis acid at low temperatures in the presence of an aldehyde, or with fluoride ion together with an activated

  在几种硅烷氢化物（PhMe 2 SiH，PMHS，HMe 2 SiOSiMe 2 H）之一存在下，将烯酮暴露于催化量的[CuH（PPh 3）] 6会导致共轭还原并伴随形成相应的甲硅烷基烯醇醚。在不分离的情况下，在醛存在下在低温下用路易斯酸或氟化物离子与活化的卤化物一起对这些中间体进行处理，可在单次操作中获得良好的三组分偶联（3-CC）产物收率。反应瓶。
• [EN] FUSED RING COMPOUNDS<br/>[FR] COMPOSÉS CYCLIQUES CONDENSÉS
  申请人：GENENTECH INC

  公开号：WO2020035031A1

  公开（公告）日：2020-02-20

  Provided are fused ring compounds of Formula (I), Formula (II), or Formula (III), as further detailed herein, which are used for the inhibition of Ras proteins, as well as compositions comprising these compounds and methods treatment by their administration.

  提供的是公式(I)、公式(II)或公式(III)的融合环化合物，具体细节如下，这些化合物用于抑制Ras蛋白，以及包含这些化合物的组合物和通过其给药的治疗方法。

表征谱图