(+/-)-anti-4-Methyl-5-nonanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-anti-4-Methyl-5-nonanol
• 英文别名: (4S,5R)-4-methylnonan-5-ol
• 化学式: C₁₀H₂₂O
• 分子量: 158.284
• InChiKey: MBZNNOPVFZCHID-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基-5-壬酮 在 lithium aluminium tetrahydride 作用下， 以2.439%的产率得到
  参考文献：
  名称：

  β-甲醇的合成：烷基链长对铁锈红线虫非对映选择性和新引诱剂的影响

  摘要：

  通过 Felkin-Anh 模型的加成反应中加合物的非对映选择性受大体积基团的空间效应显着影响。然而，尚未研究空间烷基链长度对非对映选择性的影响。在这项工作中，我们提出了一种用于β-甲醇外消旋合成的新策略，以使用 Felkin-Anh 模型获得各种非对映异构体比例。将烷基格氏试剂添加到 α-甲基醛中提供了非对映异构体比率为threo/erythro ≈ 2:1，而使用 LiAlH 4减少结构相关的酮提供了threo/erythro比率≈ 1:1。实验数据表明，任一侧的烷基链长度对加合物的立体选择性没有影响。对所有合成的类似物在田间对Rhynchophorus ferrugineus象鼻虫的吸引力进行了评估。在田间试验中发现五种新型衍生物，包括两种醇和三种酮，可以吸引象鼻虫。其中，3-methyldecan-4-one ( 5b ) 和 4-methyldecan-5-ol ( 11a ) 对昆虫的吸引力最大。

  DOI：

  10.1021/acs.jafc.1c01875

文献信息

• PROCESSES FOR PREPARING 4-METHYL-5-NONANONE AND 4-METHYL-5-NONANOL
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20200199053A1

  公开（公告）日：2020-06-25

  The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3), the process comprising at least a step of subjecting pentanoic anhydride of the following formula (1) and a 2-pentyl nucleophilic reagent of the following general formula (2), in which M represents Li, MgZ 1 , or ZnZ 1 , wherein Z 1 represents a halogen atom or a 2-pentyl group, to a nucleophilic substitution reaction to produce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (7), the process comprising at least steps of preparing 4-methyl-5-nonanone and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (7).

  本发明提供了一种制备下式（3）的4-甲基-5-壬酮的方法，该方法包括至少一步，即将下式（1）的戊酸酐和下式（2）的2-戊基亲核试剂进行亲核取代反应，以产生4-甲基-5-壬酮（3），以及一种制备下式（7）的4-甲基-5-壬醇的方法，该方法包括至少以下步骤：制备4-甲基-5-壬酮并将所得的4-甲基-5-壬酮和还原剂进行还原反应以产生4-甲基-5-壬醇（7）。
• Processes for preparing 4-methyl-5-nonanone and 4-methyl-5-nonanol
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US10882805B2

  公开（公告）日：2021-01-05

  The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3): the process comprising at least a step of subjecting 2-methylpentanoic anhydride of the following formula (1) and an n-butyl nucleophilic reagent of the following general formula (2) in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or an n-butyl group, to a nucleophilic substitution. reaction Coproduce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (5), the process comprising at least steps of preparing 4-methyl-5-nonanone; and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (5).

  本发明提供一种制备下式(3)的 4-甲基-5-壬酮的工艺：该工艺至少包括以下步骤：将下式(1)的 2-甲基戊酸酐和下式通式(2)的正丁基亲核试剂进行亲核取代，其中 M 代表 Li、MgZ1 或 ZnZ1，其中 Z1 代表卤原子或正丁基。反应 合成 4-甲基-5-壬酮（3），以及制备下式（5）的 4-甲基-5-壬醇的工艺，该工艺至少包括以下步骤：制备 4-甲基-5-壬酮；以及将得到的 4-甲基-5-壬酮和还原剂进行还原反应，生成 4-甲基-5-壬醇（5）。
• Structure, chirality, and field testing of a male-produced aggregation pheromone of Asian palm weevilRhynchophorus bilineatus (Montr.) (Coleoptera: Curculionidae)
  作者：A. Cameron Oehlschlager、R. N. B. Prior、Alice L. Perez、Regine Gries、Gerhard Gries、Harold D. Pierce、Sam Laup

  DOI：10.1007/bf02035156

  日期：1995.10

  4-Methyl-5-nonanol is a male-produced aggregation pheromone of the Asian palm weevil, Rhynchophorus bilineatus (Montr.). The pheromone was identified by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectrometric (MS) analyses of male- and female-produced volatiles. Analyses by GC-EAD and GC-MS of weevil-produced and stereoselectively synthesized isomers of 4-methyl-5-nonanol on a Cyclodex B column, which separated isomers with baseline resolution, revealed that only (4S,5S)-4-methyl-5-nonanol is EAD active and produced by the males. In field experiments in Papua New Guinea, (4S,SS)-4-methyl-5-nonanol and a racemic mixture of disatereoisomers of it enhanced attraction of male and female weevils to sugarcane-baited traps. (4S,5S)-4-Methyl-5-nonanol is also an aggregation pheromone of two other Asian palm weevils, R. ferrugineus (Oliv.) and R. vulneratus (Panz.). The stereoisomeric mixture of 4-methyl-5-nonanol is currently used to manage populations of R. bilineatus in Papua New Guinea.
• Synthesis of β-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of <i>Rhynchophorus ferrugineus</i>
  作者：Van-Dung Le、Chi-Hien Dang、Cong-Hao Nguyen、Hong-Ung Nguyen、Thanh-Danh Nguyen

  DOI：10.1021/acs.jafc.1c01875

  日期：2021.6.2

  significantly by the steric effect of bulky groups. However, the influence of steric alkyl chain length has not been studied for the diastereoselectivity. In this work, we present a new strategy for the racemic synthesis of β-methyl alcohols to obtain various diastereomer ratios using the Felkin–Anh model. The addition of alkyl Grignard reagents to α-methyl aldehydes afforded diastereomer ratios of threo/erythro

  通过 Felkin-Anh 模型的加成反应中加合物的非对映选择性受大体积基团的空间效应显着影响。然而，尚未研究空间烷基链长度对非对映选择性的影响。在这项工作中，我们提出了一种用于β-甲醇外消旋合成的新策略，以使用 Felkin-Anh 模型获得各种非对映异构体比例。将烷基格氏试剂添加到 α-甲基醛中提供了非对映异构体比率为threo/erythro ≈ 2:1，而使用 LiAlH 4减少结构相关的酮提供了threo/erythro比率≈ 1:1。实验数据表明，任一侧的烷基链长度对加合物的立体选择性没有影响。对所有合成的类似物在田间对Rhynchophorus ferrugineus象鼻虫的吸引力进行了评估。在田间试验中发现五种新型衍生物，包括两种醇和三种酮，可以吸引象鼻虫。其中，3-methyldecan-4-one ( 5b ) 和 4-methyldecan-5-ol ( 11a ) 对昆虫的吸引力最大。