(3S,6RS)-3-methyl-6-(1-methylethenyl)-9-decenyl acetate | 64309-03-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,6RS)-3-methyl-6-(1-methylethenyl)-9-decenyl acetate
• 英文别名: (3S,6RS) 3-methyl6-isopropenyl-9-decen-1-yl acetate；9-Decen-1-ol, 3-methyl-6-(1-methylethenyl)-, acetate；[(3S)-3-methyl-6-prop-1-en-2-yldec-9-enyl] acetate
• CAS: 64309-03-1；67601-04-1；67601-06-3；67601-07-4；67601-10-9；71424-34-5；73395-36-5
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: UJJKWQRTTYLTQL-LBAUFKAWSA-N

物化性质

• 沸点：
  320.8±31.0 °C(Predicted)
• 密度：
  0.879±0.06 g/cm3(Predicted)
• LogP：
  5.850 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2915390090

反应信息

• 作为产物：
  描述：

  (3S)-1-(benzyloxy)-3,7-dimethyloct-6-ene 在 palladium on activated charcoal 吡啶 、 氢气 、 aluminum isopropoxide 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 (3S,6RS)-3-methyl-6-(1-methylethenyl)-9-decenyl acetate
  参考文献：
  名称：

  Calo, Vincenzo; Lopez, Luigi; Fiandanese, Vito, Gazzetta Chimica Italiana, 1990, vol. 120, # 9, p. 577 - 579

  摘要：

  DOI：

文献信息

• Efficient Synthesis of the Aonidiella aurantii (Mask.) Sex Pheromone Component: (3S,6RS)-3-Methyl-6-(1-Methylethenyl)-9-decenyl Acetate
  作者：Panagiotis Kefalas、Nikitas Ragoussis

  DOI：10.1055/s-1995-3966

  日期：1995.6

  The title compound, active component of the sex pheromone of Aonidiella aurantii (California Red Scale), was synthesized in three steps starting from S-citronellyl acetate with a 30% overall yield. The key feature of the synthesis is a copper salt assisted, highly regioselective attack of the 4-butenyl bromide Grignard reagent on the γ-site of the chloroallylic system of (S)-8-chloro-3,7-dimethyl-6-octenyl acetate (8a).

  标题化合物，即加州红锈粉虱（Aonidiella aurantii）性信息素的活性成分，经过三步合成，自S-柠檬烯醇乙酸酯起始，总体产率为30%。合成的关键特征是铜盐辅助下，4-丁烯基溴化格氏试剂对（S）-8-氯-3,7-二甲基-6-辛烯基乙酸酯（8a）的氯烯基体系γ位的高度区域选择性攻击。
• PROCESS FOR PREPARING 6-ISOPROPENYL-3-METHYL-9-DECENYL ACETATE, AND INTERMEDIATES THEREFOR
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20220017447A1

  公开（公告）日：2022-01-20

  The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ 1 , ZnZ 1 , Cu, CuZ 1 , or CuLiZ 1 , wherein Z 1 represents a halogen atom or a CH 2 CH 2 CH(CH 3 )CH 2 CH 2 OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

  本发明提供了一种制备6-异丙烯基-3-甲基-9-癸烯基醋酸酯（5）的方法：其中Ac代表乙酰基，该方法包括以下步骤：将在位置1具有一个离去基X的2-甲基-2,6-庚二烯化合物（1）进行亲核取代反应，其中X代表一个含有1至10个碳原子的乙酰氧基，一个含有1至10个碳原子的烷基磺酰氧基，一个含有6至20个碳原子的芳基磺酰氧基，或一个卤素原子；与在位置5具有被保护羟基的3-甲基戊基亲核试剂（2）进行亲核取代反应，其中M代表Li、MgZ1、ZnZ1、Cu、CuZ1或CuLiZ1，其中Z1代表卤素原子或CH2CH2CH(CH3)CH2CH2OR基团，R代表羟基的保护基团，形成具有在位置1处保护羟基的6-异丙烯基-3-甲基-9-癸烯化合物（3）；将具有在位置1处保护羟基的6-异丙烯基-3-甲基-9-癸烯化合物（3）进行去保护反应，形成6-异丙烯基-3-甲基-9-癸烯醇（4）；将6-异丙烯基-3-甲基-9-癸烯醇（4）醋酰化，形成6-异丙烯基-3-甲基-9-癸烯基醋酸酯（5）。
• PROCESS FOR PREPARING 6-ISOPROPENYL-3-METHYL-9-DECENYL ACETATE AND INTERMEDIATES THEREOF
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20210323903A1

  公开（公告）日：2021-10-21

  A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M 1 represents Li, MgZ 1 , ZnZ 1 , Cu, CuZ 1 , or CuLiZ 1 , wherein Z 1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X 1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).

  以下是该过程的中文翻译：制备下列式（3）的6-异丙烯基-3-甲基-9-癸烯基醋酸酯的制备过程，其中Ac代表乙酰基，该过程包括以下步骤：制备亲核试剂，下列一般式（1）的5-异丙烯基-2-甲基-8-壬烯基化合物：其中M1代表Li，MgZ1，ZnZ1，Cu，CuZ1或CuLiZ1，其中Z1代表卤素原子或5-异丙烯基-2-甲基-8-壬烯基基团，从下列一般式（4）的5-异丙烯基-2-甲基-8-壬烯基卤化物化合物制备：其中X1代表卤素原子；将亲核试剂（1）5-异丙烯基-2-甲基-8-壬烯基化合物与选择自甲醛、多聚甲醛和1,3,5-三噁烷的至少一种亲电试剂进行加成反应，随后进行水解反应以形成下列式（2）的6-异丙烯基-3-甲基-9-癸烯醇；并对6-异丙烯基-3-甲基-9-癸烯醇（2）进行乙酰化以形成6-异丙烯基-3-甲基-9-癸烯基醋酸酯（3）。
• 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。
• CALO, VINCENZO;LOPEZ, LUIGI;FIANDANESE, VITO, GAZZ. CHIM. ITAL., 120,(1990) N, C. 577-579
  作者：CALO, VINCENZO、LOPEZ, LUIGI、FIANDANESE, VITO

  DOI：——

  日期：——