trans-5-methyloct-4-ol | 59734-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-5-methyloct-4-ol
• 英文别名: (+/-)-erythro-5-Methyl-4-octanol；(4RS,5SR)-5-methyl-octan-4-ol；(4r,5s)-5-Methyl-octan-4-ol；(4R,5S)-5-methyloctan-4-ol
• CAS: 59734-23-5
• 化学式: C₉H₂₀O
• 分子量: 144.257
• InChiKey: YLTHHPQUTLMNIF-DTWKUNHWSA-N

物化性质

• 熔点：
  6.15°C (estimate)
• 沸点：
  192.9°C (estimate)
• 密度：
  0.8160

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  5
• 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

• 作为反应物：
  描述：

  trans-5-methyloct-4-ol 在 氢氧化钾 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲醇 、 苯 为溶剂， 生成 cruentol
  参考文献：
  名称：

  Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

  摘要：

  There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil, Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil, Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by male R. phoenicis and male R. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, with R. phoenicis in Cote d'Ivoire and R. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,SS)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.

  DOI：

  10.1007/bf02036199
• 作为产物：
  描述：

  (2S,3S)-(-)-3-丙基环氧乙烷甲醇 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 8.0h， 生成 trans-5-methyloct-4-ol
  参考文献：
  名称：

  Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

  摘要：

  There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil, Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil, Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by male R. phoenicis and male R. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, with R. phoenicis in Cote d'Ivoire and R. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,SS)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.

  DOI：

  10.1007/bf02036199

文献信息

• 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。
• R₃Al−R‘₃SiOTf:  Novel and Powerful Reagent System for Stereospecific Alkylation−Silylation Reactions of Epoxides
  作者：Ponnusamy Shanmugam、Masaaki Miyashita

  DOI：10.1021/ol035075x

  日期：2003.9.1

  [reaction: see text] A novel and powerful reagent system R(3)Al-R'(3)SiOTf for the one-pot alkylation-silylation reaction of epoxides was discovered, and the reactions of various epoxides with the new reagent system have been demonstrated to occur stereospecifically giving rise to the corresponding alkylation-silylation products in excellent yields.

  [反应：参见正文]发现了一种新型且功能强大的试剂体系R（3）Al-R'（3）SiOTf，用于环氧化物的一锅烷基化-甲硅烷基化反应，并且各种环氧化物与新试剂体系的反应具有证明了立体定向发生以优异的产率产生了相应的烷基化-甲硅烷基化产物。
• The Stereochemistry of Additions to Olefins. III. The Prins Reaction with cis- and trans-4-Octene
  作者：Norman A. LeBel、Ronald N. Liesemer、Enver Mehmedbasich

  DOI：10.1021/jo01038a003

  日期：1963.3
• Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)
  作者：Alice L. Perez、Gerhard Gries、Regine Gries、Robin M. Giblin-Davis、A. Cameron Oehlschlager

  DOI：10.1007/bf02036199

  日期：1994.10

  There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil, Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil, Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by male R. phoenicis and male R. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, with R. phoenicis in Cote d'Ivoire and R. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,SS)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.