3-甲基-5-己基-2-环己烯-1-酮 | 3720-17-0

• 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-己基-2-环己烯-1-酮
• 英文名称: 3-methyl-5-hexyl-2-cyclohexen-1-one
• 英文别名: 3-methyl-5-hexylcyclohex-2-en-1-one；3-methyl-5-hexyl-2-cyclohexenone；5-hexyl-3-methyl-cyclohex-2-enone；5-Hexyl-3-methyl-cyclohex-2-enon；5-Hexyl-3-methylcyclohex-2-enon；5-hexyl-3-methylcyclohex-2-en-1-one
• CAS: 3720-17-0
• 化学式: C₁₃H₂₂O
• mdl: MFCD09263631
• 分子量: 194.317
• InChiKey: ZIUUAIVSQOVUNK-UHFFFAOYSA-N

物化性质

• 沸点：
  286.2±10.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.769
• 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

反应信息

• 作为反应物：
  描述：

  3-甲基-5-己基-2-环己烯-1-酮 在 五氯化磷 作用下， 生成 3-chloro-5-hexyl-1-methyl-cyclohexa-1,3-diene
  参考文献：
  名称：

  Gundlich; Knoevenagel, Chemische Berichte, 1896, vol. 29, p. 171

  摘要：

  DOI：
• 作为产物：
  描述：

  6-hexyl-2-methyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 生成 3-甲基-5-己基-2-环己烯-1-酮
  参考文献：
  名称：

  2-甲基-4-氧代环己基-2-烯甲酸乙酯（哈格曼酯）作为烷基取代的3-甲基环己烯酮的前体

  摘要：

  由2-甲基-4-氧代环己基-2-烯基羧酸乙酯（哈格曼酯）经以下步骤制备4-烷基-3-甲基环己基-2-烯酮乙二醇缩醛的烷基化。已经探索了从哈格曼酯制得6-烷基-3-甲基环己-2-烯酮的各种途径。制备这些不饱和酮的一种特别方便的途径是使用异构的酮酯，4-甲基-2-氧代环己基-3-烯丙基羧酸乙酯作为起始原料。2-甲基-4-吡咯烷基环己-1,3-二烯羧酸乙酯（衍生自哈格曼酯的完全共轭二烯胺）的烷基化反应在水解和脱乙氧基羰基化后生成2-烷基-3-甲基环己-2-烯酮。据报道，哈格曼酯的制备方法有所改进。4-烷基-和6-烷基-3-甲基环己-2-烯酮的制备补充了现有方法，以2-烷基-和5-烷基-3-甲基环己-2-烯酮。

  DOI：

  10.1039/p19790001837

文献信息

• Formulations for control and repellency of biting arthropods
  申请人：BEDOUKIAN RESEARCH, INC.

  公开号：US10172349B2

  公开（公告）日：2019-01-08

  This disclosure relates to a method for the control or repellency of biting arthropods. The method comprises bringing the biting arthropods into contact with a biting arthropod repellent formulation. The biting arthropod repellent formulation comprises an alkoxy nootkatone separate from, or in combination, or in synergistic combination, with skin or plant derived compounds and compounds structurally similar to them (e.g., ketones, cyclic ketones, esters, gamma or delta lactones, and branched and/or unsaturated carboxylic acids), and/or one or more repellents selected from the group consisting of DEET®, para-menthane-3,8-diol (PMD), Picaridin, ethyl 3-[acetyl(butyl)amino]propanoate (IR3535), and other nitrogen-containing repellents including amines, amides, and nitrogen-containing heterocyclic compounds. This disclosure also relates to a biting arthropod repellent formulation comprising an alkoxy nootkatone separate from, or in combination, or in synergistic combination, with the skin or plant derived compounds and compounds structurally similar to them, and/or the one or more repellents.

  本公开涉及一种控制或驱赶咬人节肢动物的方法。该方法包括使咬人节肢动物与咬人节肢动物驱避制剂接触。该驱咬性节肢动物制剂包括一种烷氧基诺卡酮，它与皮肤或植物提取的化合物以及结构类似的化合物（如：酮、环酮、烷氧基诺卡酮）分开使用，或结合使用，或协同使用、酮、环酮、酯、γ 或 δ 内酯，以及支链和/或不饱和羧酸），和/或一种或多种驱避剂，这些驱避剂选自 DEET®、对位门烷-3,8-二醇 (PMD)、Picaridin、3-[乙酰（丁基）氨基]丙酸乙酯 (IR3535) 和其他含氮驱避剂，包括胺、酰胺和含氮杂环化合物。本公开还涉及一种驱咬节肢动物制剂，该制剂包含一种烷氧基诺卡酮，它与皮肤或植物提取的化合物以及结构类似的化合物和/或一种或多种驱避剂分开使用，或结合使用，或协同使用。
• Formulations for killing agricultural pests
  申请人：BEDOUKIAN RESEARCH, INC.

  公开号：US10624341B2

  公开（公告）日：2020-04-21

  Killing one or more agricultural pests is accomplished by bringing the agricultural pests into contact with a toxic amount of a formulation comprising: (I) one or more compounds selected from the group consisting of: (1) one or more compounds of structure (A), wherein the compounds of structure (A) comprise: wherein R is selected from the group consisting of —OH, ═O, —OC(O)R4, —OR6, —(OR6)2, wherein each R6 is independently selected from an alkyl group containing from 1 to 4 carbon atoms and R 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, then R can only be ═O; each Z is independently selected from the group consisting of (CH) and (CH2); y is a numeral selected from 1 and 2; R1 is selected from the group consisting of 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 selected from the group consisting of 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; R3 is selected from the group consisting of 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, —(CH2)nOH, —C(O)OR5, —CH2C(O)OR7, —CH2C(O)R8, —C(O)NR9R10, —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 (A) contain from 11 to 20 total carbon atoms; and (2) one or more sesquiterpenes selected from the group consisting of acyclic, monocyclic, bicyclic and tricyclic sesquiterpenes and derivatives thereof; and (II) one or more toxicant compounds selected from the group consisting of carbamates, organochlorines, pyrethroids, sulfoximines, neonicotinoids, pyridine azomethines, diamides, organophosphates, phenylpyrazoles, oxadiazines, and ketoenols. The formulation can be a synergistic formulation.

  杀灭一种或多种农业害虫的方法是使农业害虫接触有毒量的制剂，该制剂包括：(I)一种或多种选自以下组别的化合物：(1)一种或多种结构(A)的化合物，其中结构(A)的化合物包括： 其中R选自由-OH、═O、-OC(O)R4、-OR6、-(OR6)2组成的组，其中每个R6独立地选自含有1至4个碳原子的烷基，R是具有0至2个双键和1至15个碳原子的支链或直链、饱和或不饱和烃基；X是O或CH2，但当X是O时，则R只能是═O；每个 Z 独立地选自 (CH) 和 (CH2) 所组成的组； y 是选自 1 和 2 的数字； R1 选自 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 所组成的组； R2 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 所组成的组；R3 选自由 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、-(CH2)nOH、-C(O)OR5、-CH2C(O)OR7、-CH2C(O)R8、-C(O)NR9R10 所组成的组、-CH2C(O)NR11R12，其中 R5、R7、R8、R9、R10、R11 和 R12 各自独立选自 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，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；其中结构（A）的化合物总共含有 11 至 20 个碳原子；以及 (2) 一种或多种倍半萜，选自由无环、单环、双环和三环倍半萜及其衍生物组成的组；(II) 一种或多种有毒化合物，选自由氨基甲酸酯类、有机氯类、拟除虫菊酯类、亚砜类、新烟碱类、吡啶偶氮甲烷类、二酰胺类、有机磷酸酯类、苯基吡唑类、噁二嗪类和酮烯醇类组成的组。制剂可以是增效制剂。
• Formulations for killing biting arthropods
  申请人：BEDOUKIAN RESEARCH, INC.

  公开号：US10631536B2

  公开（公告）日：2020-04-28

  Killing one or more biting arthropods selected from the group consisting of mosquitoes, bed bugs and ticks is accomplished by bringing the biting arthropods into contact with a toxic amount of a formulation comprising: (1) one or more compounds of structure (I), wherein the compounds of structure (I) comprise: wherein R is selected from the group consisting of —OH, ═O, —OC(O)R4, —OR6, —(OR6)2, wherein each R6 is independently selected from 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, then R can only be ═O; each Z is independently selected from the group consisting of (CH) and (CH2); y is a numeral selected from 1 and 2; R1 is selected from the group consisting of 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 selected from the group consisting of 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; R3 is selected from the group consisting of 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, —(CH2)nOH, —C(O)OR5, —CH2C(O)OR7, —CH2C(O)R8, —C(O)NR9R10, —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 11 to 20 total carbon atoms; and (2) one or more toxicant compounds selected from the group consisting of pyrethroids, carbamates, and organophosphates. The formulation can be a synergistic formulation.

  杀灭一种或多种咬人节肢动物的方法是从蚊子、臭虫和蜱组成的组中选出的一种或多种咬人节肢动物，其方法是使咬人节肢动物接触有毒量的制剂，该制剂包括：(1) 一种或多种结构(I)的化合物，其中结构(I)的化合物包括： 其中R选自由-OH、═O、-OC(O)R4、-OR6、-(OR6)2组成的组，其中每个R6独立地选自含有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、饱和或不饱和烃基：X是O或CH2，但当X是O时，R只能是═O；每个Z独立地选自(CH)和(CH2)组成的组；y是选自1和2的数字；R1 选自 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 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；R3 选自由 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、-(CH2)nOH、-C(O)OR5、-CH2C(O)OR7、-CH2C(O)R8、-C(O)NR9R10 所组成的组、-CH2C(O)NR11R12，其中 R5、R7、R8、R9、R10、R11 和 R12 各自独立选自 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，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；其中结构（I）的化合物总共含有 11 至 20 个碳原子；以及 (2) 一种或多种从拟除虫菊酯、氨基甲酸酯和有机磷组成的组中选出的毒性化合物。制剂可以是增效制剂。
• Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs
  申请人：BEDOUKIAN RESEARCH, INC.

  公开号：US10785978B2

  公开（公告）日：2020-09-29

  Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs is obtained by contact of the insects with at least one of the compounds of the structure (I) wherein R is —OH, ═O, —OC(O)R4, —OR6, or —(OR6)2, wherein 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 and 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 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, or —CH2C(O)NR11R12 where each of R5, R7, R8, R9, R10, R11 and R12 is independently 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, and n is n 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 11 to 20 carbon atoms except where R is ═O, X═CH2 and y is 1 the compounds of structure (I) contain from 13 to 20 carbon atoms, with the proviso that when R3 is —CH2C(O)OR7 R1 and R2 must be H or a saturated hydrocarbyl group with zero double bonds. The invention also includes optical isomers, diastereomers and enantiomers of the compounds of structure (I).

  通过昆虫与至少一种结构式（I）的化合物接触，可控制和驱赶咬人的苍蝇、家蝇、蜱虫、蚂蚁、跳蚤、咬人的蠓虫、蟑螂、蜘蛛和臭虫。 其中 R是-OH、═O、-OC(O)R4、-OR6或-(OR6)2，其中每个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 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； R3 是 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、 或-CH2C(O)NR11R12，其中 R5、R7、R8、R9、R10、R11 和 R12 各自独立地为 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，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；以及 其中结构(I)的化合物含有11至20个碳原子，但当R为═O、X═CH2和y为1时，结构(I)的化合物含有13至20个碳原子，但当R3为-CH2C(O)OR7时，R1和R2必须为H或饱和烃基，且双键为零。本发明还包括结构（I）化合物的光学异构体、非对映异构体和对映体。
• Synergistic biting arthropod repellent formulations
  申请人：BEDOUKIAN RESEARCH, INC.

  公开号：US11252959B2

  公开（公告）日：2022-02-22

  This disclosure relates to a method for the control or repellency of biting arthropods. The method comprises bringing the biting arthropods into contact with a biting arthropod repellent formulation. The biting arthropod repellent formulation comprises nootkatone in combination, or in synergistic combination, with skin or plant derived compounds and compounds structurally similar to them (e.g., ketones, cyclic ketones, esters, gamma or delta lactones, and branched and/or unsaturated carboxylic acids), and/or one or more repellents selected from the group consisting of DEET®, para-menthane-3,8-diol (PMD), Picaridin, ethyl 3-[acetyl(butyl)amino]propanoate (IR3535), and other nitrogen-containing repellents including amines, amides, and nitrogen-containing heterocyclic compounds. This disclosure also relates to a biting arthropod repellent formulation comprising nootkatone in combination, or in synergistic combination, with the skin or plant derived compounds and compounds structurally similar to them, and/or the one or more repellents.

  本公开涉及一种控制或驱赶咬人节肢动物的方法。该方法包括使咬人节肢动物与咬人节肢动物驱避制剂接触。咬人节肢动物驱避制剂包括与皮肤或植物提取的化合物以及结构类似的化合物（例如酮、环酮、酯、γ 或 δ 内酯，以及支链和/或不饱和羧酸），和/或一种或多种选自以下组别的驱虫剂：DEET®、对位门烷-3,8-二醇（PMD）、Picaridin、3-[乙酰（丁基）氨基]丙酸乙酯（IR3535），以及其他含氮驱虫剂，包括胺、酰胺和含氮杂环化合物。本公开还涉及一种驱咬节肢动物制剂，该制剂由诺卡通与皮肤或植物衍生化合物以及结构类似的化合物和/或一种或多种驱避剂组合而成，或协同组合而成。