[(R)-2,2-dimethyl-3-(1-methylethylidene)cyclobutyl]methyl (S)-2-methylbutanoate

• 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: [(R)-2,2-dimethyl-3-(1-methylethylidene)cyclobutyl]methyl (S)-2-methylbutanoate
• 英文别名: (R)-maconelliyl (S)-2-methybutanoate；[(1R)-2,2-dimethyl-3-propan-2-ylidenecyclobutyl]methyl (2S)-2-methylbutanoate
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: HVQKRWVVKAOHNS-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  熏衣草醇 、 (S)-(+)-2-甲基丁酸 、 [(R)-2,2-dimethyl-3-(1-methylethylidene)cyclobutyl]methyl (S)-2-methylbutanoate 以 甲醇 为溶剂， 以gave 75 mg (75% yield) of 1a as clear oil的产率得到(R)-2-isopropenyl-5-methylhex-4-enyl (S)-2-methylbutanoate
  参考文献：
  名称：

  Attractant pheromone for the male pink hibiscus mealybug, Maconellicoccus hirsutus (Green) (Homoptera: Pseudococcidae)

  摘要：

  一种吸引雄性粉色木槿粉介壳虫的组合物，包含载体材料或载体以及有效量的(R)-薰衣草醇(S)-2-甲基丁酸酯和(R)-马科内利醇(S)-2-甲基丁酸酯。还公开了一种吸引雄性粉色木槿粉介壳虫到物体或区域的方法，该方法涉及使用有效量的(R)-薰衣草醇(S)-2-甲基丁酸酯和(R)-马科内利醇(S)-2-甲基丁酸酯处理该物体或区域。环丁烷，2,2-二甲基-3-(1-甲基乙烯基)环丁烷，其化学式为：其中R1是氢，C1-11直链或支链醇，醛，烷基，醚（例如甲醇，乙醛，4-甲基己烷，庚氧甲烷）或其与C1-10饱和或不饱和，直链或支链酸（例如甲酸，乙酸，2-甲基丁酸，3-甲基-2-丁烯酸）的酯，R2是氢，甲基，C1-10饱和或不饱和，直链或支链烷基（例如己烷，异丙烯基，4-甲基-4-戊烯）。一种干扰雄性粉色木槿粉介壳虫与雌性粉色木槿粉介壳虫交配的方法，涉及将粉色木槿粉介壳虫种群暴露于含有(R)-薰衣草醇(S)-2-甲基丁酸酯和(R)-马科内利醇(S)-2-甲基丁酸酯的粉色木槿粉介壳虫交配干扰有效量的组合物中，以及可选的载体材料或载体。

  公开号：

  US08062651B1
• 作为产物：
  描述：

  (+)-cis-pinononoic acid 在 吡啶 、 lithium aluminium tetrahydride 、 甲基锂 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 50.75h， 生成 [(R)-2,2-dimethyl-3-(1-methylethylidene)cyclobutyl]methyl (S)-2-methylbutanoate
  参考文献：
  名称：

  粉色芙蓉Mealybug，Maconellicoccus hirsutus雌性信息素的对映体选择性合成。

  摘要：

  粉色芙蓉粉虱（Maconellicoccus hirsutus，绿色）是一种外来害虫，最近入侵南加州和佛罗里达州。雌性hirsutus释放一种新型的环丁烷单萜醇（马可奈醇）的2-甲基丁酸，它与2-甲基丁酸的lavandulyl一起构成性信息素，以吸引远距离的雄性。据报道，来自α-pine烯的主要成分的四种不同立体异构体的对映异构体合成是1，2-甲基丁酸Macellelliyl 2-methylbutanoate。已经建立了天然存在的2-甲基丁酸马来烯基酯1和次要成分2-甲基丁酸lavandulyl 2的绝对构型。

  DOI：

  10.1021/jf048198k

文献信息

• Process for Production of Polysubstituted Cyclobutanes and Polysubstituted Cyclobutenes
  申请人：Takasu Kiyosei

  公开号：US20080051598A1

  公开（公告）日：2008-02-28

  The prior art required specialized substrates or reaction conditions to be used to manufacture polysubstituted cyclobutane compounds and polysubstituted cyclobutene compounds, and the method had poor generality. The type or quantity of the catalyst or solvent used was also problematic in the industrial manufacture of polysubstituted cyclobutane compounds. The present invention provides a method for manufacturing a polysubstituted cyclobutane compound with high stereoselectivity that has low environmental load (is ecologically advantageous) and is applicable to industrial manufacturing from the standpoint of operation, substrate generality, catalyst, solvent, and efficiency. A polysubstituted cyclobutane, a cyclobutene, and a bicyclo[4.2.0]octane compound can be manufactured efficiently, stereoselectively, and in an ecologically advantageous manner by causing a Brønsted acid to act on a mixture of an enol ether compound or 2-siloxydiene compound with an alkene or alkyne compound in which a carbonyl group is substituted at the 1-position in a non-aqueous solvent or without a solvent.

  先前的技术要求使用专门的基质或反应条件来制造多取代环丁烷化合物和多取代环丁烯化合物，该方法的普适性较差。在工业生产多取代环丁烷化合物时，所使用的催化剂或溶剂的类型或数量也存在问题。本发明提供了一种制造高立体选择性、环境负荷低（具有生态优势）且从操作、基质普适性、催化剂、溶剂和效率的角度适用于工业生产的多取代环丁烷化合物的方法。通过使Brønsted酸作用于烯醚化合物或2-硅氧基二烯化合物与烯烃或炔烃化合物的混合物，其中在1位取代了羰基基团，可以在非水溶剂或无溶剂的情况下高效、立体选择性地、具有生态优势地制造多取代环丁烷、环丁烯和双环[4.2.0]辛烷化合物。
• METHOD FOR EFFECTIVELY CONTROLLING COCCOIDEA INSECT PESTS
  申请人：Ecologia Y Proteccion Agricola, S.L.

  公开号：EP3732964A1

  公开（公告）日：2020-11-04

  The present invention relates to a method for determining the effective flow rate of at least one semiochemical for controlling at least one coccoid insect pest using an artificial semiochemical matrix, and use of the effective flow rate for effectively controlling at least one coccoid insect pest through the diffusion of at least one semiochemical.

  本发明涉及一种利用人工半化学物质基质确定至少一种半化学物质的有效流速以控制至少一种茧翅目害虫的方法，以及利用该有效流速通过至少一种半化学物质的扩散有效控制至少一种茧翅目害虫的方法。
• METHOD FOR EFFECTIVELY CONTROLLING COCCOID INSECT PESTS
  申请人：Ecología y Protección Agrícola, S.L.

  公开号：US20210059246A1

  公开（公告）日：2021-03-04

  The present invention relates to a method for determining the effective flow rate of at least one semiochemical for controlling at least one coccoid insect pest using an artificial semiochemical matrix, and use of the effective flow rate for effectively controlling at least one coccoid insect pest through the diffusion of at least one semiochemical.
• US8062651B1
  申请人：——

  公开号：US8062651B1

  公开（公告）日：2011-11-22
• Attractant pheromone for the male pink hibiscus mealybug, Maconellicoccus hirsutus (Green) (Homoptera: Pseudococcidae)
  申请人：The United States of America as represented by the Secretary of Agriculture

  公开号：US08062651B1

  公开（公告）日：2011-11-22

  A composition for attracting male pink hibiscus mealybugs which contains a carrier material or carrier and effective amount of (R)-lavandulyl (S)-2-methylbutanoate and (R)-maconelliyl (S)-2-methylbutanoate. Also a method for attracting male pink hibiscus mealybugs to an object or area, which method involves treating said object or area with effective amount of (R)-lavandulyl (S)-2-methylbutanoate and (R)-maconelliyl (S)-2-methylbutanoate. Cyclobutanes, 2,2-dimethyl-3-(1-methylethylidene)cyclobutanes, having the formula: wherein R1 is hydrogen, a C1-11 straight or branched alcohol, aldehyde, alkyl, ether (e.g. methanol, ethanal, 4-methylhexane, heptyloxymethane), or esters thereof with a C1-10 saturated or unsaturated, straight or branched acid (e.g., formic acid, acetic acid, 2-methylbutyric acid, 3-methyl-2-butenoic acid) and R2 is hydrogen, methyl, C1-10 saturated or unsaturated, straight or branched alkyl (e.g. hexane, isopropenyl, 4-methyl-4-pentene). A method of disrupting male pink hibiscus mealybug mating with female pink hibiscus mealybugs, involving exposing a pink hibiscus mealybug population to a composition containing a pink hibiscus mealybug mating disrupting effective amount of (R)-lavandulyl (S)-2-methylbutanoate and (R)-maconelliyl (S)-2-methylbutanoate, and optionally a carrier material or carrier.

  一种吸引雄性粉红木槿介壳虫的组合物，包含载体材料或载体以及(R)-薰衣草醇(S)-2-甲基丁酸酯和(R)-马科内醇(S)-2-甲基丁酸酯的有效量。还涉及一种将雄性粉红木槿介壳虫吸引到物体或区域的方法，该方法涉及用(R)-薰衣草醇(S)-2-甲基丁酸酯和(R)-马科内醇(S)-2-甲基丁酸酯的有效量处理所述物体或区域。环丁烷，2,2-二甲基-3-(1-甲基乙烯基)cyclobutanes，具有以下结构式：其中R1为氢，C1-11直链或支链醇，醛，烷基，醚（例如甲醇，乙醛，4-甲基己烷，庚氧甲烷）或其酯与C1-10饱和或不饱和，直链或支链酸（例如甲酸，乙酸，2-甲基丁酸，3-甲基-2-丁烯酸）和R2为氢，甲基，C1-10饱和或不饱和，直链或支链烷基（例如己烷，异丙烯基，4-甲基-4-戊烯）。一种打乱雄性粉红木槿介壳虫与雌性粉红木槿介壳虫交配的方法，涉及将粉红木槿介壳虫群体暴露在含有(R)-薰衣草醇(S)-2-甲基丁酸酯和(R)-马科内醇(S)-2-甲基丁酸酯的粉红木槿介壳虫交配干扰有效量的组合物中，并可选择性地包含载体材料或载体。