3-甲基-5-乙基-2-环戊烯-1-酮 | 40920-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲基-5-乙基-2-环戊烯-1-酮
• 中文别名: 5-乙基-3-甲基环己-2-烯酮
• 英文名称: 3-methyl-5-ethylcyclohex-2-en-1-one
• 英文别名: 5-ethyl-3-methyl-2-cyclohexenone；5-ethyl-3-methylcyclohex-2-enone；5-ethyl-3-methylcycohex-2-enone；5-ethyl-3-methyl-cyclohex-2-enone；5-Aethyl-3-methyl-cyclohex-2-enon；3-Methyl-5-ethyl-2-cyclohexen-1-on；5-ethyl-3-methylcyclohex-2-en-1-one
• CAS: 40920-68-1
• 化学式: C₉H₁₄O
• mdl: MFCD07780565
• 分子量: 138.21
• InChiKey: XULZXXRNQOYNIW-UHFFFAOYSA-N

物化性质

• 沸点：
  212 °C
• 密度：
  0.910
• 闪点：
  84 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000
• 储存条件：
  存储条件：2-8°C，干燥且密封。

反应信息

• 作为反应物：
  描述：

  3-甲基-5-乙基-2-环戊烯-1-酮 在 palladium on activated charcoal 作用下， 以 乙醇 为溶剂， 生成 3-methyl-5-ethyl-cyclohexanone
  参考文献：
  名称：

  质谱的立体化学分配：3,5-二烷基环己叉基乙酸酯和3-烷基-2-链烯酸酯的双键几何异构体

  摘要：

  质谱是的构任务的最佳物理方法ë -和Z-3,5- dialkylcyclohexylidene乙酸酯1和ë -和ž -3-烷基-2-烯酸酯2。导致从1丢失C-3和C-5烷基以及从2丢失两个δ-烷基的均烯丙基裂解是立体有择的过程：与羰基相邻的基团的丢失是特别优选的。该断裂的立体特异性是根据碳-碳键裂解之前的隐藏氢转移来解释的。

  DOI：

  10.1016/s0040-4020(01)96456-7
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 3-甲基-5-乙基-2-环戊烯-1-酮
  参考文献：
  名称：

  Wallach, Justus Liebigs Annalen der Chemie, 1902, vol. 323, p. 145

  摘要：

  DOI：

文献信息

• Dienediolates of unsaturated carboxylic acids in synthesis. Synthesis of cyclohexenones and polycyclic ketones by tandem Michael-Dieckmann decarboxylative annulation of unsaturated carboxylic acids.
  作者：María J. Aurell、Pablo Gaviña、Ramon Mestres

  DOI：10.1016/s0040-4020(01)86973-8

  日期：1994.2

  Substituted 2-cyclohexenones 4 to 7 and hexaxydronaphthalenones and hexahydroindenones 13 to 18 are prepared by tandem Michael-Dieckmann addition of lithium dienediolates of acyclic and alicyclic unsaturated carboxylic acids to the lithium salts of the same or other unsaturated carboxylic acids.

  通过将无环和脂环式不饱和羧酸的二烯二醇锂串联加入相同或其他不饱和羧酸的锂盐中来制备取代的2-环己烯酮4至7和六氢萘二烯酮和六氢茚并酮13至18。
• Reaction of CH-acids with Michael acceptors in the presence of potassium carbonate. Syntheses of 6-acetyl- and 3,5-dialkylcyclohex-2-enones
  作者：D. S. Khachatryan、A. A. Vardapetyan、N. M. Morlyan、A. L. Razinov、K. R. Matevosyan

  DOI：10.1007/s11172-015-0873-y

  日期：2015.2

  The reaction of acetylacetone with α,β-enones in the presence of potassium carbonate affords 6-acetylcyclohex-2-enones. The assembly of two acetoacetate and one alkanal molecules gives 3,5-dialkylcyclohex-2-enones. Facile one-pot procedures for these reactions were developed.

  在碳酸钾存在下，乙酰丙酮与 α、β-烯酮反应生成 6-乙酰基环己-2-烯酮。将两个乙酰乙酸酯分子和一个烷烃分子组装在一起可得到 3,5-二烷基环己-2-烯酮。为这些反应开发了简便的一锅反应程序。
• Ground state sigmatropic and electrocyclic rearrangements in some monoterpenes
  作者：K.J. Crowley、S.G. Traynor

  DOI：10.1016/0040-4020(78)88420-8

  日期：1978.1

  Alloocimene 7, obtained via ocimene 6 by heating α-pinene 2, was further pyrolysed to a complex mixture of products derived primarily from antarafacial 1,7- and suprafacial 1,5-hydrogen migrations, and 6-eleetron disrotatory electrocyclizations.

  通过加热α- pine烯2经由香菜烯6获得的同种香菜烯7，进一步热解成主要来自对苯二酸1，7-和超1，5-氢迁移以及6-电子旋解电环化的产物的复杂混合物。
• Feeding deterrence of pests such as Hemiptera, Lepidoptera and Coleoptera
  申请人：BEDOUKIAN RESEARCH, INC.

  公开号：US11224223B2

  公开（公告）日：2022-01-18

  Compounds are used as agents that deter feeding by insect pests, such as Hemiptera, Lepidoptera and Coleoptera. Feeding deterrence is obtained by contact of the insect pests with at least one of the compounds of the structure (I) wherein R is —OH, ═O, —OC(O)R4, —OR6, or —(OR6)2, each R6 is independently an alkyl group containing from 1 to 4 carbon atoms and R4 is a branched or straight chain, saturated or unsaturated, hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms; X is O or CH2 with the proviso that when X is O, R can only be ═O; each Z is independently (CH) or (CH2); y is a numeral selected from 1 and 2; R1 is H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to two double bonds and from 1 to 15 carbon atoms; R2 is H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms; R3 is selected from H, a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms, —(CH2)nOH, —C(O)OR5, —CH2C(O)OR7, —CH2C(O)R8, —C(O)NR9R10, and —CH2C(O)NR11R12 where each of R5, R7, R8, R9, R10, R11 and R12 is independently selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 15 carbon atoms and n is an integer of from 1 to 12; the bond between the 2 and 3 positions in the ring structure may be a single or a double bond; and wherein the compounds of structure (I) contain from 9 to 20 total carbon atoms in the compounds.

  化合物可用作阻止半翅目、鳞翅目和鞘翅目等害虫取食的制剂。通过害虫与至少一种结构式为 (I) 的化合物接触，可阻止害虫取食。 其中 R 是 -OH、═O、-OC(O)R4、-OR6 或 -(OR6)2，每个 R6 独立地是含有 1 至 4 个碳原子的烷基，R4 是具有 0 至 2 个双键和 1 至 15 个碳原子的支链或直链、饱和或不饱和的烃基；X 是 O 或 CH2，但当 X 是 O 时，R 只能是═O；每个 Z 独立地是（CH）或（CH2）； y 是选自 1 和 2 的数字； R1 是 H 或具有 0 至 2 个双键和 1 至 15 个碳原子的支链或直链、饱和或不饱和烃基； R2 是 H 或具有 0 至 3 个双键和 1 至 15 个碳原子的支链或直链、饱和或不饱和烃基；R3 选自 H、具有 0 至 3 个双键和 1 至 15 个碳原子的支链或直链、饱和或不饱和烃基、-(CH2)nOH、-C(O)OR5、-CH2C(O)OR7、-CH2C(O)R8、-C(O)NR9R10 和-CH2C(O)NR11R12，其中 R5、R7、R8、R9、R10 和 R11R12 各自R7、R8、R9、R10、R11 和 R12 都独立选自 H 和具有 0 至 3 个双键和 1 至 15 个碳原子的支链或直链、饱和或不饱和烃基，且 n 为 1 至 12 的整数；环结构中 2 位和 3 位之间的键可以是单键或双键；结构（I）的化合物中总共含有 9 至 20 个碳原子。
• Dienediolates of Unsaturated Carboxylic Acids in Synthesis. Tandem Michael Diechmann Synthesis of Substituted 2-Cyclohexenones
  作者：M. J. Aurell、P. Gaviña、S. Gil、A. Tortajada、R. Mestres

  DOI：10.1080/00397919108021772

  日期：1991.9

  3,5-Disubstituted 2-Cyclohexenones are prepared by tandem Michael-Dieckmann addition of lithium dienediolates of dimethylacrylic and beta-methylcinnamic acids to lithium carboxylates of unsaturated carboxylic acids.

表征谱图