(2R,3R,7R,9S)-3,7,9-Trimethyltridecan-2-ol | 249746-09-6

• 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: (2R,3R,7R,9S)-3,7,9-Trimethyltridecan-2-ol
• CAS: 249746-09-6
• 化学式: C₁₆H₃₄O
• 分子量: 242.445
• InChiKey: CYWPZFWYONZUAG-ZJIFWQFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  17
• 可旋转键数：
  10
• 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：

  (2R,3R,7R,9S)-3,7,9-Trimethyltridecan-2-ol 在 氢氧化钾 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (2S,3R,7R,9S)-3,7,9-trimethyl-2-tridecyl acetate
  参考文献：
  名称：

  Sex Pheromone of the Pine Sawfly, Macrodiprion nemoralis. Stereoselective Synthesis of the Sixteen Stereoisomers of 3,7,9-Trimethyl-2-tridecyl Acetate.

  摘要：

  The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-gamma-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.

  DOI：

  10.3891/acta.chem.scand.53-0620
• 作为产物：
  描述：

  (2S,4S)-2,4-dimethyl-1-octanol 在 氢氧化钾 、 lithium 、 一水合肼 、 三苯基膦 作用下， 以 四氯化碳 、 正己烷 、 二乙二醇 为溶剂， 反应 7.42h， 生成 (2R,3R,7R,9S)-3,7,9-Trimethyltridecan-2-ol
  参考文献：
  名称：

  Sex Pheromone of the Pine Sawfly, Macrodiprion nemoralis. Stereoselective Synthesis of the Sixteen Stereoisomers of 3,7,9-Trimethyl-2-tridecyl Acetate.

  摘要：

  The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-gamma-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.

  DOI：

  10.3891/acta.chem.scand.53-0620

文献信息

• Pheromones of Pine Sawflies: Synthesis of a Pure (2S,3R)-3-Methylalkan-2-ol Stereoisomer via an Asymmetric 1,3-Dipolar Cycloaddition; Preparation of a Pheromone Component of Macrodiprion nemoralis
  作者：Staffan Karlsson、Hans-Erik Högberg

  DOI：10.1055/s-2000-8221

  日期：——

  paper presents a new approach to the preparation of enantiomerically pure (2S,3R)-3-methylalkan-2-ols, the esters of which are sex pheromones of several pine sawflies. Thus, an asymmetric 1,3-dipolar cycloaddition between a sulfur containing 1,3-dipole and a dipolarophile attached to (1R)-camphorsultam containing a vinyl ether functionality furnished a 90 : 10 diastereomeric mixture of trans-3,4-disubstituted

  本文提出了一种制备对映体纯 (2S,3R)-3-methylalkan-2-ols 的新方法，其酯类是几种松叶蜂的性信息素。因此，含硫的 1,3-偶极子和连接到含有乙烯基醚官能团的 (1R)-樟脑磺胺的亲偶极试剂之间的不对称 1,3-偶极环加成反应提供了 90:10 的反式 3,4-二取代四氢噻吩的非对映异构体混合物酰胺。主要的转化为对映体纯的四氢噻吩基甲基溴，其与单烷基化二噻烷单元偶联。经雷尼镍还原(2S,3R,7R,9S)-3,7,9-trimethyltridecan-2-ol，其乙酸酯即为Macrodiprion nemoralis的引诱性信息素成分。