(±)-(3-nonyloxiran-2-yl)methanol

• 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: (±)-(3-nonyloxiran-2-yl)methanol
• 英文别名: rac-(cis)-3-nonyloxiranemethanol；[(2R,3S)-3-nonyloxiran-2-yl]methanol
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: WFHRKQDHNGOVPA-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-(3-nonyloxiran-2-yl)methanol 在 Lindlar's catalyst 2,6-二甲基吡啶 、 喹啉 、 正丁基锂 、 氢气 、 环己烯 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 rac-(cis)-(2Z,5Z-octadienyl)-3-nonyloxirane
  参考文献：
  名称：

  Improved Synthesis and Deployment of (2S,3R)-2-(2Z,5Z-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth, Lymantria mathura

  摘要：

  We report two new syntheses of (2S,3R)-2-(2Z5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled in the final step with 2-iodomethyl-3-nonyloxirane 4 via a Grignard reaction. The second approach employed alkylation of 1,4-heptadiynyllithium with epoxy triflates 7 in ether/hexane and provided the pheromone in greater than or equal to37% overall yield from alcohol 2. The 4:1 ratio of pheromone enantiomers, reportedly the most attractive to pink moth males, can be directly crafted from appropriately selected Sharpless asymmetric epoxidation conditions.

  DOI：

  10.1021/jf035506q
• 作为产物：
  描述：

  1-十一炔 在 sodium tetrahydroborate 、 正丁基锂 、 氢气 、 nickel(II) acetate tetrahydrate 、 乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 42.17h， 生成 (±)-(3-nonyloxiran-2-yl)methanol
  参考文献：
  名称：

  Scalable synthesis of the pink gypsy moth Lymantria mathura sex pheromone (–)-mathuralure

  摘要：

  Mathuralure(1)是粉色鬼蛾Lymantria mathura的主要性信息素成分，这是一种对北美地区可能具有毁灭性的入侵物种。为了支持对这种蛾的种群监测，开发了克级合成（-）-mathuralure(1)的方法。该过程依赖于将炔基锂物种与氯环氧烷偶联，并在10步反应中以10%的收率提供天然产物。

  DOI：

  10.1139/cjc-2012-0376

文献信息

• 10.3390/molecules29092136
  作者：Zhou, Yun、Wang, Jianan、Tian, Beijing、Zhu, Yanwei、Zhang, Yujuan、Han, Jinlong、Zhong, Jiangchun、Shan, Chenggang

  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。
• Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin
  作者：Anthony G. M. Barrett、John Head、Marie L. Smith、Nicholas S. Stock、A. J. P. White、D. J. Williams

  DOI：10.1021/jo9905672

  日期：1999.8.1

  The total synthesis of (+)-pramanicin (41b) is reported, thereby establishing the relative and absolute stereochemistry of the naturally occurring antifungal agent. The key steps involve (i) conjugate addition of the diethyl((diethylamino)diphenylsilyl)zincate to a suitably protected gamma-lactam 3 and quenching of the resultant enolate with the alpha,beta-unsaturated gamma,delta-epoxy aldehyde 2 (X = H), (ii) Ni(acac)(2)-catalyzed hydroxylation of a beta-dicarbonyl array, and (iii) Fleming-Tamao oxidation to reveal the masked C-3 hydroxyl group.
• ROUSH, WILLIAM R.;ANDO, KAORI;POWERS, DANIEL B.;PALKOWITZ, ALAN D.;HALTER+, J. AMER. CHEM. SOC., 112,(1990) N7, C. 6339-6348
  作者：ROUSH, WILLIAM R.、ANDO, KAORI、POWERS, DANIEL B.、PALKOWITZ, ALAN D.、HALTER+

  DOI：——

  日期：——
• Improved Synthesis and Deployment of (2<i>S</i>,3<i>R</i>)-2-(2<i>Z</i>,5<i>Z</i>-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth, <i>Lymantria mathura</i>
  作者：Ashot Khrimian、James E. Oliver、Roger C. Hahn、Nikki H. Dees、Jeff White、Victor C. Mastro

  DOI：10.1021/jf035506q

  日期：2004.5.1

  We report two new syntheses of (2S,3R)-2-(2Z5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled in the final step with 2-iodomethyl-3-nonyloxirane 4 via a Grignard reaction. The second approach employed alkylation of 1,4-heptadiynyllithium with epoxy triflates 7 in ether/hexane and provided the pheromone in greater than or equal to37% overall yield from alcohol 2. The 4:1 ratio of pheromone enantiomers, reportedly the most attractive to pink moth males, can be directly crafted from appropriately selected Sharpless asymmetric epoxidation conditions.
• Scalable synthesis of the pink gypsy moth <i>Lymantria mathura</i> sex pheromone (–)-mathuralure
  作者：Jeffrey Mowat、James Senior、Baldip Kang、Robert Britton

  DOI：10.1139/cjc-2012-0376

  日期：2013.3

  Mathuralure (1) is the major sex pheromone component of the pink gypsy moth Lymantria mathura, a potentially devastating invasive species to North America. To support population monitoring of this moth, a gram-scale synthesis of (–)-mathuralure (1) was developed. This process relies on coupling an alkynyl lithium species with a chloroepoxide and provides access to the natural product in a 10% yield over 10 steps.

  Mathuralure(1)是粉色鬼蛾Lymantria mathura的主要性信息素成分，这是一种对北美地区可能具有毁灭性的入侵物种。为了支持对这种蛾的种群监测，开发了克级合成（-）-mathuralure(1)的方法。该过程依赖于将炔基锂物种与氯环氧烷偶联，并在10步反应中以10%的收率提供天然产物。