(R)-2-methyl-octyl toluene-4-sulfonate | 254435-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-methyl-octyl toluene-4-sulfonate
• 英文别名: (R)-2-methyloctyl tosylate；[(2R)-2-methyloctyl] 4-methylbenzenesulfonate
• CAS: 254435-67-1
• 化学式: C₁₆H₂₆O₃S
• 分子量: 298.447
• InChiKey: JGHNKVLIRYVZGS-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-octyl toluene-4-sulfonate 在 六甲基磷酰三胺 、 sodium amalgam 、 正丁基锂 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 52.0h， 生成 (meso-7,11)-7,11-dimethylheptadecane
  参考文献：
  名称：

  7-甲基十七烷和 7,11-二甲基十七烷的所有立体异构体的合成、春铁杉活套钩和松木活套钩的雌性信息素成分

  摘要：

  7-甲基十七烷 (1) 和 7,11-二甲基十七烷 (2) 的所有立体异构体都是从香茅醇 (3) 和 3-羟基-2-甲基丙酸甲酯 (8) 的对映异构体开始合成的。从内消旋 2,6-二甲基庚二酸 [(2R,6S)-21] 开始，实现了内消旋 7,11-二甲基十七烷 [(7R,11S)-2] 的短时间合成。(S)-1 和 (7R,11S)-2 的混合物是春天铁杉弯钩蛾 (Lambdina athasaria) 和松树弯针蛾 (L. pellucidaria) 的信息素。

  DOI：

  10.1002/(sici)1099-0690(199911)1999:11<3139::aid-ejoc3139>3.0.co;2-8
• 作为产物：
  描述：

  (R)-2-methyloctanal 在 dimethyl sulfide borane 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 20.75h， 生成 (R)-2-methyl-octyl toluene-4-sulfonate
  参考文献：
  名称：

  7,11-二甲基十七烷和7-甲基十七烷的所有立体异构体，春季铁杉弯钩和弯形松木弯钩的雌信息素成分的不对称合成

  摘要：

  描述了使用SAMP / RAMP method方法通过α-烷基化不对称合成7,11-二甲基十七烷（1）和7-甲基十七烷（2）的立体异构体，具有高的不对称诱导和良好的总收率。（7 S，11 R）-1和（S）-2的混合物是女性生产的春季铁杉弯loop蛾（Lambdina athasaria）和松柏弯pine蛾（Lambdina pellucidaria）的性信息素。它们都是北美东北部的森林害虫。

  DOI：

  10.1016/s0040-4039(02)00595-6

文献信息

• Synthesis of the (5S,9R)-isomer of 5,9-dimethylpentadecane, the major component of the female sex pheromone of the coffee leaf miner moth, Leucoptera coffeella
  作者：Kenji Mori

  DOI：10.1016/j.tetasy.2008.03.016

  日期：2008.4

  (5S,9R)-5,9-Dimethylpentadecane, one of the stereoisomers of the major component of the female sex pheromone of the coffee leaf miner moth (Leucoptera coffeella), was synthesized by starting from (R)-3-methyl-4-butanolide and (S)-citronellal. (C) 2008 Elsevier Ltd. All rights reserved.

  （5S,9R)-5,9-二甲基十五烷是一种立体异构体，属于咖啡黑果蠹蛾（Leucoptera coffeella）雌性性外激素的主要成分，该化合物通过以（R)-3-甲基-4-丁氧基乙酸内酯和（S)-香叶醛为起始原料进行合成。© 2008 Elsevier Ltd. 保留所有权利。
• Sex pheromone of the pine sawflyDiprion pini (Hymenoptera: Diprionidae): Chemical identification, synthesis and biological activity
  作者：G. Bergström、A. -B. Wassgren、O. Anderbrant、J. Fägerhag、H. Edlund、E. Hedenström、H. -E. Högberg、C. Geri、M. A. Auger、M. Varama、B. S. Hansson、J. Löfqvist

  DOI：10.1007/bf01928898

  日期：1995.4

  The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (> 99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R) -3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a nonchiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 mu g of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 mu g in France and 50 mu g in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.
• The Synthesis of Deoxyfusapyrone. 2. Preparation of the Bis-Trisubstituted Olefin Fragment and Its Attachment to the Pyrone Moiety
  作者：Michael G. Organ、Junquan Wang

  DOI：10.1021/jo034371k

  日期：2003.7.1

  A convergent and modular synthesis has been devised to construct the eight diastereoisomers of deoxyfusapyrone (1). In this paper the synthesis of the complex polyene chain is reported as is its connection to the pyrone moiety that is in the middle of the structure of the final target molecule. This route has been fully worked out for one of the isomers and will now be applied in a parallel synthesis format to make all the stereoisomers of 1.