(S)-2-methyloctyl tosylate | 117555-29-0

• 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: (S)-2-methyloctyl tosylate
• 英文别名: (S)-2-Methyl-1-octanol tosylate；(S)-2-methyloctyl 4-methylbenzenesulfonate；[(2S)-2-methyloctyl] 4-methylbenzenesulfonate
• CAS: 117555-29-0
• 化学式: C₁₆H₂₆O₃S
• 分子量: 298.447
• InChiKey: JGHNKVLIRYVZGS-HNNXBMFYSA-N

物化性质

• 沸点：
  401.3±14.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

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：

  (S)-2-methyloctyl tosylate 在 lithium bromide 作用下， 以 丙酮 为溶剂， 生成 (S)-(+)-1-bromo-2-methyloctane
  参考文献：
  名称：

  松锯齿的性信息素。分离自新双pr虫的一些活性次要成分的手性合成和乙酸二吡啶酯的一些手性类似物的手性合成。

  摘要：

  一些类似物的手性合成，2 - 7，3,7-二甲基-2-十五烷醇，的1（diprionol），以及相应的乙酸酯的描述。1的乙酸盐是Neodiprion属（Diprionidae）的性信息素中的主要引诱剂。化合物2/2-4被鉴定为分离自新双孢虫雌性雌性的次要成分。从手性起始原料，要么制备的合成中间体，通过不对称合成，或通过面包酵母减少。

  DOI：

  10.1016/s0040-4020(01)92255-0
• 作为产物：
  描述：

  (S)-1-amino-2-(methoxymethyl)pyrrolidine 在 盐酸 、 dimethyl sulfide borane 、 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 正戊烷 为溶剂， 反应 54.0h， 生成 (S)-2-methyloctyl tosylate
  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 All the Stereoisomers of 7-Methylheptadecane and 7,11-Dimethylheptadecane, the Female Sex Pheromone Components of the Spring Hemlock Looper and the Pitch Pine Looper
  作者：Yasuo Shirai、Masanori Seki、Kenji Mori

  DOI：10.1002/(sici)1099-0690(199911)1999:11<3139::aid-ejoc3139>3.0.co;2-8

  日期：1999.11

  the stereoisomers of 7-methylheptadecane (1) and 7,11-dimethylheptadecane (2) were synthesized by starting from the enantiomers of citronellol (3) and methyl 3-hydroxy-2-methylpropanonate (8), respectively. A short synthesis of meso-7,11-dimethylheptadecane [(7R,11S)-2] was achieved starting from meso-2,6-dimethylheptanedioic acid [(2R,6S)-21]. A mixture of (S)-1 and (7R,11S)-2 is the pheromone of the

  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。
• Sex Pheromone of pine sawflies. Chiral syntheses of some active minor components isolated from neodiprion sertifer and of some chiral analogues of diprionyl acetate.
  作者：Erik Hedenström、Hans-Erik Högberg、Ann-Britt Wassgren、Gunnar Bergström、Jan Löfqvist、Bill Hansson、Olle Anderbrant

  DOI：10.1016/s0040-4020(01)92255-0

  日期：1992.4

  some analogues, 2 – 7, of 3,7-dimethyl-2-pentadecanol, 1 (diprionol), and of the corresponding acetates are described. The acetate of 1 is the main attractant in the sex pheromone of the Neodiprion genus (Diprionidae). Compounds 2 /2- 4 were identified as minor components isolated from females of Neodiprion sertifer. Synthetic intermediates were prepared either from chiral starting materials, via asymmetric

  一些类似物的手性合成，2 - 7，3,7-二甲基-2-十五烷醇，的1（diprionol），以及相应的乙酸酯的描述。1的乙酸盐是Neodiprion属（Diprionidae）的性信息素中的主要引诱剂。化合物2/2-4被鉴定为分离自新双孢虫雌性雌性的次要成分。从手性起始原料，要么制备的合成中间体，通过不对称合成，或通过面包酵母减少。
• Mori, Kenji; Horikiri, Hiromasa, Liebigs Annalen, 1996, # 4, p. 501 - 505
  作者：Mori, Kenji、Horikiri, Hiromasa

  DOI：——

  日期：——
• US2023/10658
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.