[(1R)-3-异亚丙基-2,2-二甲基环丁基]甲醇 | 754227-26-4

• 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
• 中文名称: [(1R)-3-异亚丙基-2,2-二甲基环丁基]甲醇
• 中文别名: 5(4H)-异噻唑酮并,3-(1-乙基环丙基)-(9CI)
• 英文名称: (R)-(-)-[2,2-dimethyl-3-(1-methylethylidene)cyclobytyl] methanol
• 英文别名: [(R)-(-)-2,2-dimethyl-3-(1-methylethylidene)cyclobutyl]methanol；(R)-maconelliol；(R)-(-)-maconelliol；maconelliol；[(1R)-2,2-dimethyl-3-propan-2-ylidenecyclobutyl]methanol
• CAS: 754227-26-4
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: QFTXQVXOZUNRNH-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：

  (S)-2-甲基丁酰氯 、 [(1R)-3-异亚丙基-2,2-二甲基环丁基]甲醇 在 吡啶 作用下， 以 苯 为溶剂， 生成 [(R)-2,2-dimethyl-3-(1-methylethylidene)cyclobutyl]methyl (R)-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
• 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 49.75h， 生成 [(1R)-3-异亚丙基-2,2-二甲基环丁基]甲醇
  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

• 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。
• Structure–Function Studies of <i>Artemisia tridentata</i> Farnesyl Diphosphate Synthase and Chrysanthemyl Diphosphate Synthase by Site-Directed Mutagenesis and Morphogenesis
  作者：J. Scott Lee、Jian-Jung Pan、Gurusankar Ramamoorthy、C. Dale Poulter

  DOI：10.1021/jacs.7b07608

  日期：2017.10.18

  chain-elongation activity, while similar mutations in the active site of FPPase failed to significantly promote formation of significant amounts of irregular monoterpenes. Our results indicate that CPPase, a promiscuous enzyme, is more plastic toward acquiring new activities, whereas FPPase is more resistant. Mutations of residues outside of the α terpene synthase fold are important for acquisition of FPPase

  来自 Artemisia tridentata ssp 的法呢基二磷酸合酶 (FPPase) 和菊基二磷酸合酶 (CPPase) 的氨基酸序列。Spiciformis，减去它们的叶绿体靶向区域，71% 相同，90% 相似。FPPase 通过将异戊烯基二磷酸 (IPP) 与二甲基烯丙基二磷酸 (DMAPP) 偶联，然后再与香叶基二磷酸 (GPP) 偶联，有效且选择性地合成“常规”倍半萜类法呢基二磷酸 (FPP)。相比之下，CPPase 是一种低效的混杂酶，它从两个分子的 DMAPP 中合成“不规则”单萜菊酯二磷酸 (CPP)、薰衣草二磷酸 (LPP) 和微量的马可二磷酸 (MPP)，并将 IPP 与 DMAPP 偶联以形成给 GPP。A. tridentata FPPase 和 CPPase 属于链延长蛋白家族 (PF00348)，萜类合酶超家族 (CL0613) 的一个亚群，其成员具有特征性
• Chiral synthesis of maconelliol: a novel cyclobutanoid terpene alcohol from pink hibiscus mealybug, Maconellicoccus hirsutus
  作者：Aijun Zhang、Junying Nie、Ashot Khrimian

  DOI：10.1016/j.tetlet.2004.10.131

  日期：2004.12

  The chiral synthesis of maconelliol, [2,2-dimethyl-3-(1-methylethylidene)cyclobutyl] methanol, the alcohol moiety of the major sex pheromone component isolated from the pink hibiscus mealybug, Maconellicoccus hirsutus, is described. The compound was synthesized in six steps from alpha-pinene and the key step is dehydration of 5 to 7 through the intermediate 6. The absolute configuration of the naturally occurring maconelliol was determined as R. (C) 2004 Elsevier Ltd. All rights reserved.
• A Common Mechanism for Branching, Cyclopropanation, and Cyclobutanation Reactions in the Isoprenoid Biosynthetic Pathway
  作者：Hirekodathakallu V. Thulasiram、Hans K. Erickson、C. Dale Poulter

  DOI：10.1021/ja0771282

  日期：2008.2.1

  Four reactions-chain elongation, cyclopropanation, branching, and cyclobutanation-are used in nature to join isoprenoid units for construction of the carbon skeletons for over 55 000 naturally occurring isoprenoid compounds. Those molecules produced by chain elongation have head-to-tail (regular) carbon skeletons, while those from cyclopropanation, branching, or cyclobutanation have non-head-to-tail (irregular) skeletons. Although wild type enzymes have not been identified for the branching and cyclobutanation reactions, chimeric proteins constructed from farnesyl diphosphate synthase (chain elongation) and chrysanthemyl diphosphate synthase (cyclopropanation) catalyze all four of the known isoprenoid coupling reactions to give a mixture of geranyl diphosphate (chain elongation), chrysanthemyl diphosphate (cyclopropanation), lavandulyl diphosphate (branching), and maconelliyl and planococcyl diphosphate (cyclobutanation). Replacement of the hydrogen atoms at C1 or C2 or hydrogen atoms in the methyl groups of dimethylallyl diphosphate by deuterium alters the distribution of the cyclopropanation, branching, and cyclobutanation products through primary and secondary kinetic isotope effects on the partitioning steps of common carbocationic intermediates. These experiments establish the sequence in which the intermediates are formed and indicate that enzyme-mediated control of the carbocationic rearrangement and elimination steps determines the distribution of products.
• US8062651B1
  申请人：——

  公开号：US8062651B1

  公开（公告）日：2011-11-22