1,4,4,5-Tetramethyl-3-hydroxymethyl-1-cyclopenten

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,4,4,5-Tetramethyl-3-hydroxymethyl-1-cyclopenten
• 英文别名: (3,4,5,5-Tetramethylcyclopent-2-enyl)methanol；3,4,5,5-tetramethyl-2-cyclopentene-1-methanol；(3,4,5,5-Tetramethylcyclopent-2-en-1-yl)methanol
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: KMSIDXMGNKQFNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4,4,5-Tetramethyl-3-hydroxymethyl-1-cyclopenten 、 异丁酸酐 在 4-二甲氨基吡啶 作用下， 以94 %的产率得到α-necrodylisobutyrate
  参考文献：
  名称：

  WO2023/96997

  摘要：

  公开号：
• 作为产物：
  描述：

  3,3,4,5-tetramethyl-2-vinylhex-5-en-1-ol 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 1,4,4,5-Tetramethyl-3-hydroxymethyl-1-cyclopenten
  参考文献：
  名称：

  WO2023/96997

  摘要：

  公开号：

文献信息

• [EN] COMPOSITIONS AND METHODS FOR MEALYBUG MONITORING AND CONTROL<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE SURVEILLANCE ET DE LUTTE CONTRE LES COCHENILLES
  申请人：THE STATE OF ISRAEL MINISTRY OF AGRICULTURE & RURAL DEVELOPMENT AGRICULTURAL RES ORGANIZATION ARO VO

  公开号：WO2021064719A1

  公开（公告）日：2021-04-08

  A preparation comprising gamma-necrodyl isobutyrate and an agriculturally acceptable carrier is disclosed for the monitoring and control of mealybugs. Methods of synthesizing the preparation and other mealybug pheromones that feature a necrodane structure are also disclosed.

  本发明揭示了一种包含γ-死亡脂肪酸异丁酯和农业可接受载体的制剂，用于监测和控制粉虱。还揭示了合成该制剂和其他具有死亡脂肪酸酯结构的粉虫信息素的方法。
• Synthesis of the Grape Mealybug Pheromone trans-alpha-Necrodyl Isobutyrate
  申请人：Trécé Inc.

  公开号：US20210206711A1

  公开（公告）日：2021-07-08

  Methods are provided for synthesizing the grape mealybug pheromone, trans-α-necrodyl isobutyrate, starting with essential plant oils that contain trans-α-necrodyl acetate. The synthesis method, in two steps, converts the trans-α-necrodyl acetate to trans-α-necrodol and then converts the trans-α-necrodol to the desired trans-α-necrodyl isobutyrate. The first step can be achieved by either of a hydrolysis reaction or a reduction reaction. In the hydrolysis reaction, the essential oil is mixed in an alcohol solvent with a hydroxide base, or by mixing the essential oil in an aqueous acid. A reduction reaction can instead by performed in an organic solvent in the presence of a reducing agent. The trans-α-necrodol is converted to the desired trans-α-necrodyl isobutyrate by an esterification reaction with a carboxylic acid, an acyl halide, or an acid anhydride.
• [DE] SYNERGISTEN ZUR VERSTÄRKUNG DER WIRKUNG VON REPELLENTIEN<br/>[EN] SYNERGISTS FOR BOOSTING THE ACTION OF REPELLENTS<br/>[FR] SYNERGISTES SERVANT A RENFORCER L'EFFET DE REPULSIFS
  申请人：MERCK PATENT GMBH

  公开号：WO2006105842A1

  公开（公告）日：2006-10-12

  [EN] The invention relates to the use of at least one cycloaliphatic compound selected from the group of cycloaliphatic carboxylic acid, ester of a cycloaliphatic carboxylic acid, amide of a cycloaliphatic carboxylic acid, cycloaliphatic alcohol and cycloaliphatic ketone as a synergist for boosting the action of repellents in cosmetic and dermatological formulations for repelling and/or protecting against arthropods on the skin or on a surface, and also to corresponding new preparations and their production.
  [FR] L'invention concerne l'utilisation d'au moins un composé cycloaliphatique sélectionné dans le groupe comprenant l'acide carboxylique cycloaliphatique, un ester d'un acide carboxylique cycloaliphatique, un amide d'un acide carboxylique cycloaliphatique, un alcool cycloaliphatique et une cétone cycloaliphatique, comme synergiste pour renforcer l'effet de répulsifs dans des formulations cosmétiques et dermatologiques, appliquées sur la peau ou une surface, permettant de se protéger contre les arthropodes et/ou de repousser ces derniers. L'invention concerne également de nouvelles préparations correspondantes ainsi que leur production.
  [DE] Die Erfindung betrifft die Verwendung mindestens einer cycloaliphatischen Verbindung ausgewählt aus der Gruppe cycloaliphatische Carbonsäure, Ester einer cycloaliphatischen Carbonsäure, Amid einer cycloaliphatischen Carbonsäure, cycloaliphatischer Alkohol und cycloaliphatisches Keton, als Synergist zur Verstärkung der Wirkung von Repellenten in kosmetischen und dermatologischen Formulierungen zur Abwehr und/oder Abschreckung von Arthropoden auf der Haut oder einer Oberfläche sowie entsprechende neue Zubereitungen und deren Herstellung.
• [EN] SYNTHESIS OF THE GRAPE MEALYBUG PHEROMONE TRANS-ALPHA-NECRODYL ISOBUTYRATE<br/>[FR] SYNTHÈSE DE LA PHÉROMONE DES COCHENILLES DE LA VIGNE, L'ISOBUTYRATE TRANS-ALPHA-NÉCRODYLE
  申请人：TRECE INC

  公开号：WO2021137994A1

  公开（公告）日：2021-07-08

  Methods are provided for synthesizing the grape mealybug pheromone, trans-alpha-necrodyl isobutyrate, starting with essential plant oils that contain trans-alpha-necrodyl acetate. The synthesis method, in two steps, converts the trans-alpha-necrodyl acetate to trans-alpha-necrodol and then converts the trans-alpha-necrodol to the desired trans-alpha-necrodyl isobutyrate. The first step can be achieved by either of a hydrolysis reaction or a reduction reaction. In the hydrolysis reaction, the essential oil is mixed in an alcohol solvent with a hydroxide base, or by mixing the essential oil in an aqueous acid. A reduction reaction can instead by performed in an organic solvent in the presence of a reducing agent. The trans-alpha-necrodol is converted to the desired trans-alpha-necrodyl isobutyrate by an esterification reaction with a carboxylic acid, an acyl halide, or an acid anhydride.