2,6-dimethyl-8-(3-methyl-3-sulfolen-2-yl)-2,6E-octadiene | 94987-60-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,6-dimethyl-8-(3-methyl-3-sulfolen-2-yl)-2,6E-octadiene
• 英文别名: (2'E)-2-(3',7'-dimethylocta-2',6'-dienyl)-3-methyl-2,5-dihydrothiophen 1,1-dioxide；2-<(2E)-3,7-dimethyl-2,6-octadienyl>-3-methyl-3-thiolene 1,1-dioxide；2-geranyl-3-methylsulpholene；2-(E-3,7-dimethyl-2,6-octadienyl)-3-methylsulfolene；(E)-2-(3,7-Dimethyl-2,6-octadienyl)-2,5-dihydro-3-methyl-thiophene 1,1-Dioxide；2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-methyl-2,5-dihydrothiophene 1,1-dioxide
• CAS: 94987-60-7
• 化学式: C₁₅H₂₄O₂S
• 分子量: 268.42
• InChiKey: RONBRCFGNCVGHQ-MDWZMJQESA-N

物化性质

• 沸点：
  407.2±34.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷；二甲基亚砜；乙酸乙酯;甲苯

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-8-(3-methyl-3-sulfolen-2-yl)-2,6E-octadiene 在 3,5-二甲基吡唑 、 chromium(VI) oxide 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 2.0h， 生成 6-甲基-5-庚烯-2-酮
  参考文献：
  名称：

  Spicer, Julie A.; Brimble, Margaret A.; Rowan, Daryl D., Australian Journal of Chemistry, 1993, vol. 46, # 12, p. 1929 - 1940

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-2,5-二氢噻吩-1,1-二氧化物 、 (Z)-neryl bromide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到2,6-dimethyl-8-(3-methyl-3-sulfolen-2-yl)-2,6E-octadiene
  参考文献：
  名称：

  Desai, Shailesh R.; Gore, Vinayak K.; Bhat, Sujata V., Synthetic Communications, 1990, vol. 20, # 4, p. 523 - 533

  摘要：

  DOI：

文献信息

• Stereoselective one-step syntheses of trans-β-ocimene and α-farnesene
  作者：Ta-Shue Chou、His-Hwa Tso、Lee-Jean Chang

  DOI：10.1039/c39840001323

  日期：——

  Protected forms of trans-β-ocimene and α-farnesene where synthesized in one step by direct deprotonation of 2,5-dihydro-3-methylthiophene-1,1-dioxide (6) followed by alkylation with suitable allylic bromides; this approach provides a regioselective and stereoselective introduction of an isoprene unit onto a pre-existing skeleton.

  通过直接将2，5-二氢-3-甲基噻吩-1，1-二氧化物（6）去质子化，然后用合适的烯丙基溴烷基化，一步合成合成反式-β-西门烯和α-法呢烯的保护形式；该方法提供了异戊二烯单元的区域选择性和立体选择性的引入到预先存在的骨架上。
• [EN] FUNCTIONALISATION OF 1,3-ALPHA-DIENES (II)<br/>[FR] FONCTIONNALISATION DE 1,3-ALPHA-DIÈNES (II)
  申请人：DSM IP ASSETS BV

  公开号：WO2021130059A1

  公开（公告）日：2021-07-01

  The present invention relates to the functionalisation of specific 1,3-alpha-dienes (by hydroboration). These functionalized 1,3-alpha-dienes are important intermediates in organic synthesis (especially in the synthesis of carotenoids, vitamin A and/or vitamin A derivatives).

  本发明涉及特定的1,3-α-二烯的功能化（通过氢硼化）。这些功能化的1,3-α-二烯是有机合成中的重要中间体（尤其是在类胡萝卜素、维生素A和/或维生素A衍生物的合成中）。
• The synthesis of d6-α-farnesene
  作者：Simon Fielder、Daryl D. Rowan

  DOI：10.1002/jlcr.2580341111

  日期：1994.11

  D6-α-Farnesene (3,7-dimethyl-11-2H3-methyl-12,12,12-2H3-dodeca-1,3E,6E,10-tetraene) has been synthesised by two routes. Thermolysis of 2-geranyl-3-methylsulpholene (5) yielded unlabelled α-farnesene (93%) which was epoxidized at Δ10 in 31% yield. Oxidative cleavage of the epoxide (42%) and Wittig elaboration of the resultant trienal with d6-isopropyl triphenylphosphorane gave d6-α-farnesene (73%). Alternatively, selective epoxidation of (5) gave the terminal 6′,7′ mono-epoxide in 74% yield. Oxidative cleavage (73%) and Wittig elaboration of the resultant aldehyde yielded deuterated 2-geranyl-3-methylsulpholene (46%). Thermal elimination of sulphur dioxide afforded the title compound in 91% yield.

  D6-α-法呢烯（3,7-二甲基-11-2H3-甲基-12,12,12-2H3-十二碳-1,3E,6E,10-四烯）可通过两种途径合成。2-香叶基-3-甲基硫醇（5）的热解可生成未标记的α-法呢烯（93%），后者在Δ10处发生环氧化反应，产率为31%。环氧化物的氧化裂解（42%）和Wittig反应生成的三烯醇与d6-异丙基三苯基膦的反应可生成d6-α-法呢烯（73%）。另一种方法是选择性地使（5）发生环氧化反应，生成末端6′,7′单环氧化物，产率为74%。氧化裂解（73%）和Wittig反应生成的醛可生成氘代2-香叶基-3-甲基硫醇（46%）。二氧化硫的热消除反应可生成标题化合物，产率为91%。
• Polunin, E. V.; Kharchevnikov, A. P.; Kashin, A. N., Russian Journal of Organic Chemistry, 1995, vol. 31, # 5, p. 717 - 720
  作者：Polunin, E. V.、Kharchevnikov, A. P.、Kashin, A. N.

  DOI：——

  日期：——
• Revisiting the Male-Produced Aggregation Pheromone of the Lesser Mealworm,<i>Alphitobius diaperinus</i>(Coleoptera, Tenebrionidae): Identification of a Six-Component Pheromone from a Brazilian Population
  作者：Marla J. Hassemer、Josué Sant’Ana、Miguel Borges、David Withall、John A. Pickett、Márcio W. M. de Oliveira、Raul A. Laumann、Michael A. Birkett、Maria C. Blassioli-Moraes

  DOI：10.1021/acs.jafc.6b02235

  日期：2016.9.14

  The lesser mealworm, Alphitobius diaperinus Panzer 1797 (Coleoptera: Tenebrionidae), is a cosmopolitan insect pest affecting poultry production. Due to its cryptic behavior, insecticide control is usually not efficient. Thus, sustainable and effective methods would have an enormous and positive impact in poultry production. The aim of this study was to confirm the identity of the male-produced aggregation pheromone for a Brazilian population of A. diaperinus and to evaluate its biological activity in behavioral assays. Six male-specific compounds were identified: (R)-limonene (1), (E)-ocimene (2), 2-nonanone (3), (S)-linalool (4), (R)-daucene (5), all described before in an American population, and a sixth component, (E,E)-alpha-farnesene (6), which is apparently exclusive to a Brazilian population. Y-Tube bioassays confirmed the presence of a male-produced aggregation pheromone and showed that all components need to be present in a similar ratio and concentration as emitted by male A. diaperinus to produce a positive chemotactic response.

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