(6Z,9S,10R)-9,10-epoxy-6-henicosene | 108034-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (6Z,9S,10R)-9,10-epoxy-6-henicosene
• 英文别名: 9R,10S-Epoxy-6Z-heneicosene；(2S,3R)-2-[(Z)-oct-2-enyl]-3-undecyloxirane
• CAS: 108034-04-4
• 化学式: C₂₁H₄₀O
• 分子量: 308.548
• InChiKey: FUYHMWQJTBTPIW-NWXHSOSZSA-N

物化性质

• 沸点：
  388.4±11.0 °C(Predicted)
• 密度：
  0.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (9S,10S)-9-hydroxy-10-tosyloxyheneicosadec-6-yne 在 Lindlar's catalyst 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (6Z,9S,10R)-9,10-epoxy-6-henicosene
  参考文献：
  名称：

  A facile synthetic method for chiral 1,2-epoxides and the total synthesis of chiral pheromone epoxides

  摘要：

  Chiral 1,2-epoxy-3-alkanol tosylates were successfully synthesized from alkynols in three steps using the Sharpless AD reaction as a key step in good yields. Two chiral insect pheromone epoxides were smoothly obtained from the corresponding key intermediate. (C) 1999 Elsevier Science Ltd. All rig;hts reserved.

  DOI：

  10.1016/s0957-4166(99)00082-8

文献信息

• Access to unsaturated chiral epoxides. Part II. Synthesis of a component of the sex pheromone of Phragmatobia fuliginosa
  作者：J Soulié、T Boyer、J.Y Lallemand

  DOI：10.1016/0957-4166(95)00046-r

  日期：1995.2

  A general method for the synthesis of chiral cis-epoxides substituted bearing a saturated chain and an unsaturated chain is described. This method is used to synthesize both enantiomers of compound 1.

  描述了合成带有饱和链和不饱和链的被取代的手性顺式环氧化物的一般方法。该方法用于合成化合物1的两种对映异构体。
• Synthesis of the Four Components of the Female Sex Pheromone of the Painted Apple Moth,<i>Teia anartoides</i>
  作者：Shin-etsu MUTO、Kenji MORI

  DOI：10.1271/bbb.67.1559

  日期：2003.1

  Four pheromone components of the female painted apple moth (Teia anartoides), an Australian insect pest, were synthesized. These were (Z)-6-henicosen-11-one (1), (6Z, 8E)-6,8-henicosadien-11-one (2), (Z)-cis-9,10-epoxy-6-henicosene (3), and (Z)-cis-9,10-epoxy-6-icosene (4). 2-Dodecanone was converted to 1 and 2, and both the enantiomers of 3 and 4 were synthesized from the enantiomers of 4-tert-bu

  合成了澳大利亚害虫苹果雌蛾（Teia anartoides）的四个信息素成分。这些是（Z）-6-henicosen-11-one（1），（6Z，8E）-6,8-henicosadien-11-one（2），（Z）-cis-9,10-epoxy-6-亚油（3）和（Z）-顺-9,10-环氧-6-二十烷（4）。将2-十二烷酮转化为1和2，并且由4-叔丁基二甲基甲硅烷氧基-顺式2，3-环氧-1-丁醇的对映体合成3和4的对映体。
• Pheromone Synthesis; CXXXIX.¹Enzymatic Preparation of (2<i>S</i>,3<i>R</i>)-4-Acetoxy-2,3-epoxybutan-1-ol and Its Conversion to the Epoxy Pheromones of the Gypsy Moth and the Ruby Tiger Moth
  作者：Jean-Luc Brevet、Kenji Mori

  DOI：10.1055/s-1992-26290

  日期：——

  Pig pancreatic lipase-catalyzed asymmetric hydrolysis of 1, 4-diacet-oxy-cis-2,3-epoxybutane yielded (2S,3R) -4-acetoxy-2,3-epoxybu-tan-1-ol, which was converted to two naturally occurring epoxides: the gypsy moth pheromone, disparlure [(7R,8S)-7,8-epoxy-2-methyloctadecane] and the ruby tiger moth pheromone [(6Z,9S,10R) -9,10-epoxy-6-henicosene].

  在猪胰脂肪酶催化下，1, 4-二乙酰氧基-顺式-2,3-环氧丁烷发生不对称水解，生成 (2S,3R) -4-乙酰氧基-2,3-环氧布坦-1-醇，并转化为两种天然环氧化物： 吉普赛蛾信息素 disparlure [(7R,8S)-7,8-epoxy-2-methyloctadecane] 和红宝石虎蛾信息素 [(6Z,9S,10R)-9,10-epoxy-6-henicosene]。
• Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth
  作者：Yun Zhou、Jianan Wang、Beijing Tian、Yanwei Zhu、Yujuan Zhang、Jinlong Han、Jiangchun Zhong、Chenggang Shan

  DOI：10.3390/molecules29092136

  日期：——

  A concise synthesis of the sex pheromones of elm spanworm as well as painted apple moth has been achieved. The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown’s P2-Ni reduction. This approach provided the sex pheromone of the elm spanworm (1) in 31% total yield and those of the painted apple moth (2, 3) in 26% and 32% total yields. The ee values of three final

  实现了榆树蛾和苹果蛾性信息素的简明合成。关键步骤是乙炔离子的烷基化、Sharpless不对称环氧化和Brown's P2-Ni还原。该方法提供的榆树蛾 (1) 的性信息素总产量为 31%，苹果蛾 (2, 3) 的性信息素总产量为 26% 和 32%。三种最终产品的ee值均达到99%。合成的信息素在管理和控制这些害虫方面具有广阔的应用前景。
• Ebata, Takashi; Mori, Kenji, Agricultural and Biological Chemistry, 1989, vol. 53, # 3, p. 801 - 804
  作者：Ebata, Takashi、Mori, Kenji

  DOI：——

  日期：——