((2S,3R)-3-nonyloxiran-2-yl)methanol | 148407-32-3

• 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: ((2S,3R)-3-nonyloxiran-2-yl)methanol
• 英文别名: (+)-(2R,3R)-2,3-epoxydodecan-1-ol；(2S,3R)-3-nonyloxiranemethanol；(2S-cis)-3-nonyloxiranemethanol；(2S-cis)-3-Nonyloxirane methanol；[(2S,3R)-3-nonyloxiran-2-yl]methanol
• CAS: 148407-32-3
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: WFHRKQDHNGOVPA-NEPJUHHUSA-N

物化性质

• 沸点：
  283.5±8.0 °C(predicted)
• 密度：
  0.927±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：

  ((2S,3R)-3-nonyloxiran-2-yl)methanol 在 copper(l) iodide 、 正丁基锂 、 氯化二乙基铝 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 (2R,3S)-2-nonyl-3-(octa-2,5-diynyl)oxirane
  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
• 作为产物：
  描述：

  反式-2-十二烯-1-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到((2S,3R)-3-nonyloxiran-2-yl)methanol
  参考文献：
  名称：

  Fleming−Tamao Oxidation and Masked Hydroxyl Functionality:  Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin

  摘要：

  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.

  DOI：

  10.1021/jo9905672

文献信息

• 2,3-epoxy derivatives as anti retrovital chemotherapeutic agents
  申请人：The United States of America as represented by the Secretary of the

  公开号：US05190969A1

  公开（公告）日：1993-03-02

  The present invention is related to compounds, compositions and methods of treating viral infections. Compounds of the present invention have the following general formula: ##STR1## wherein R is selected from --CH.sub.2 OH, --CO.sub.2 R.sup.2, --CONR.sup.3 R.sup.4, or COR.sup.5, wherein R.sup.2 is hydrogen or a lower alkyl group, R.sup.3 and R.sup.4 are each independently hydrogen or a lower alkyl group, R.sup.5 is an amino acid residue bound via a terminal nitrogen or peptide having at least two amino acid residues; and wherein R.sup.1 is C.sub.5 -C.sub.13 alkyl, aryl, aralkyl, aralkyl(lower alkyl) ether, or C.sub.5 -C.sub.13 alkyl (lower alkyl)ether.

  本发明涉及化合物、组合物和治疗病毒感染的方法。本发明的化合物具有以下一般式：##STR1## 其中R从--CH.sub.2 OH，--CO.sub.2 R.sup.2，--CONR.sup.3 R.sup.4或COR.sup.5中选择，其中R.sup.2是氢或较低的烷基基团，R.sup.3和R.sup.4分别独立地是氢或较低的烷基基团，R.sup.5是通过末端氮原子结合的氨基酸残基或至少具有两个氨基酸残基的肽；其中R.sup.1为C.sub.5 -C.sub.13烷基，芳基，芳基烷基，芳基烷基(较低烷基)醚，或C.sub.5 -C.sub.13烷基(较低烷基)醚。
• 2,3-epoxy alcohols, acids and derivatives as anti retroviral
  申请人：The United States of America as represented by the Department of Health

  公开号：US06153589A1

  公开（公告）日：2000-11-28

  The present invention is related to compounds, compositions and methods of treating viral infections. Compounds of the present invention have the following general formula: ##STR1## wherein R is selected from --CH.sub.2 OH, --CO.sub.2 R.sup.2, --CONR.sup.3 R.sup.4, or COR.sup.5, wherein R.sup.2 is hydrogen or a lower alkyl group, R.sup.3 and R.sup.4 are each independently hydrogen or a lower alkyl group, R.sup.5 is an amino acid residue bound via a terminal nitrogen or peptide having at least two amino acid residues; and wherein R.sup.1 is C.sub.5 -C.sub.13 alkyl, aryl, aralkyl, aralkyl(lower alkyl)ether, or C.sub.5 -C.sub.13 alkyl(lower alkyl)ether.

  本发明涉及化合物、组合物和治疗病毒感染的方法。本发明的化合物具有以下一般式：##STR1## 其中，R从--CH.sub.2 OH、--CO.sub.2 R.sup.2、--CONR.sup.3 R.sup.4或COR.sup.5中选择，其中R.sup.2为氢或低碳基，R.sup.3和R.sup.4各自独立地为氢或低碳基，R.sup.5为通过末端氮键合的氨基酸残基或至少具有两个氨基酸残基的肽；其中R.sup.1为C.sub.5-C.sub.13烷基、芳基、芳基烷基、芳基烷基（低碳基）醚或C.sub.5-C.sub.13烷基（低碳基）醚。
• 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。
• 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.
• US5190969A
  申请人：——

  公开号：US5190969A

  公开（公告）日：1993-03-02