(E)-2-octen-1-yl methanesulfonate | 119306-15-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (E)-2-octen-1-yl methanesulfonate
• 英文别名: (E)-2-octenyl methanesulfonate；[(E)-oct-2-enyl] methanesulfonate
• CAS: 119306-15-9
• 化学式: C₉H₁₈O₃S
• 分子量: 206.306
• InChiKey: MUPFNLHYEZHYQR-BQYQJAHWSA-N

物化性质

• 沸点：
  310.8±21.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (E)-2-octen-1-yl methanesulfonate 在 sodium periodate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 34.0h， 生成 (E)-2-octenyl p-tolyl sulfone
  参考文献：
  名称：

  Hiroi, Kunio; Makino, Kunitaka, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1727 - 1737

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基磺酰氯 、 2-octenol 在 2,3,5-三甲基吡啶 作用下， 以50%的产率得到(E)-2-octen-1-yl methanesulfonate
  参考文献：
  名称：

  摘要：

  Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50 mug) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.

  DOI：

  10.1023/a:1021005517389

文献信息

• Carbamate-Catalyzed Enantioselective Bromolactamization
  作者：Yi An Cheng、Wesley Zongrong Yu、Ying-Yeung Yeung

  DOI：10.1002/anie.201504724

  日期：2015.10.5

  A highly facile, efficient, and enantioselective bromolactamization of olefinic amides was effected by a carbamate catalyst and ethanol additive. The amide substrates underwent N‐cyclization predominantly to give a diverse range of enantioenriched bromolactam products containing up to two stereogenic centers.

  氨基甲酸酯催化剂和乙醇添加剂可实现烯烃酰胺的高度简便，高效和对映选择性的溴内酰胺化。酰胺底物主要经过N环化作用，以产生多种对映体富集的溴内酰胺产品，其中最多包含两个立体异构中心。