((2S,3S)-3-ethyloxiran-2-yl)methanol | 104530-72-5

• 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,3S)-3-ethyloxiran-2-yl)methanol
• 英文别名: (-)-(2S,3S)-2,3-Epoxy-1-pentanol；3,4-anhydro-1,2-dideoxypentitol；(2S,3S)-2,3-Epoxy-pentan-1-ol；(2S,3S)-2,3-epoxy-1-pentanol；3-(ethyloxiran-2-yl)methanol；[(2S,3S)-3-ethyloxiran-2-yl]methanol
• CAS: 104530-72-5
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: XEVKRTIYWSUXHP-WHFBIAKZSA-N

物化性质

• 沸点：
  171.3±8.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  2
• 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,3S)-3-ethyloxiran-2-yl)methanol 在 偶氮二异丁腈 三正丁基氢锡 、 magnesium iodide 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 1,2-戊二醇
  参考文献：
  名称：

  Regioselective opening of epoxy alcohols: mild chemo- and stereoselective preparation of iodohydrins and 1,2-diols

  摘要：

  Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.

  DOI：

  10.1021/jo00021a045
• 作为产物：
  描述：

  反-2-戊酸甲酯 在 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 ((2S,3S)-3-ethyloxiran-2-yl)methanol
  参考文献：
  名称：

  Mulzer, Johann; Lammer, Ortrud, Chemische Berichte, 1986, vol. 119, # 7, p. 2178 - 2190

  摘要：

  DOI：

文献信息

• Synthesis of Stegobiol and Its Oxidation to Stegobinone, the Components of the Female-Produced Sex Pheromone of the Drugstore Beetle
  作者：Kenji Mori、Satoshi Sano、Yusuke Yokoyama、Masahiko Bando、Masaru Kido

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1135::aid-ejoc1135>3.0.co;2-k

  日期：1998.6

  Crystalline (–)-stegobinone [(2S,3R,1′R)]-2,3-dihydro-2,3,5-trimethyl-6-(1′-methyl-2′-oxobutyl)-4H-pyran-4-one (1)], the major component of the female-produced sex pheromone of the drugstore beetle (Stegobium paniceum L.), was synthesized by oxidation of crystalline and the minor component (–)-stegobiol [(2S,3R,1′S,2′S)-2,3-dihydro-2,3,5-trimethyl-6-(2′-hydroxy-1′-methylbutyl)-4H-pyran-4-one (2)] under

  结晶 (-)-stegobinone [(2S,3R,1'R)]-2,3-dihydro-2,3,5-trimethyl-6-(1'-methyl-2'-oxobutyl)-4H-pyran- 4-一 (1)] 是药房甲虫 (Stegobium paniceum L.) 雌性性信息素的主要成分，通过结晶和次要成分 (-)-stegobiol [(2S,3R, 1'S,2'S)-2,3-dihydro-2,3,5-trimethyl-6-(2'-hydroxy-1'-methylbutyl)-4H-pyran-4-one (2)]使用 Jones 铬酸、Dess-Martin 过碘烷或 Ley 钌试剂的适当条件。后者 (2) 是通过使用脂肪酶和 Sharpless 环氧化来合成的，以引入适当的手性中心。通过X射线分析确认了1的立体结构。
• Studies towards the Identification of the Sex Pheromone of<i>Thyrinteina arnobia</i>
  作者：Jardel A. Moreira、Tiago Neppe、Marcelo M. de Paiva、Anna M. Deobald、Luciane G. Batista-Pereira、Marcio W. Paixão、Arlene G. Corrêa

  DOI：10.5935/0103-5053.20130241

  日期：——

  pest in Brazilian native plants, e.g. Psidium guajava, and exotic plants, such as Eucalyptus species. In this work we describe the isolation of the pheromone components of T. arnobia, using glands extract and solid phase micro extraction (SPME) of virgin females. The samples were analyzed by gas chromatography with an electroantennographic detector (GC-EAD), and mass spectrometry (GC-MS). Two reproducible

  紫罗兰（Algarta parda）thyrinteina arnobia（鳞翅目：Geometridae），巴西重要植物，巴西番石榴（Psidium guajava），异国情调，桉树等。阿根廷雀巢的雀巢trabalho e relatado o isolamento dos的组成部分，微粉尘外表层（SPME）的女性特征。作为通气孔菌的通气孔，作为气体质谱仪（CG-EAD）和电子质谱仪（CG-EM）。CG-EM sugeriram和3,4-epoxi-6,9-eneicosadieno como组成部分的分析物，作为电镜观察台。排在第10位的印尼总得主，占全球总收入的28％。孔雀斑菌或季戊四醇酯类环氧化合物。桉树棕环黄胸腺（Lepidoptera：Geometridae）被认为是巴西本土植物（如番石榴）和外来植物（如桉树）的重要害虫。在这项工作中，我们描述了使用原始女性的腺体提取物和固相微
• A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
  作者：Felix Urbitsch、Bryony L. Elbert、Josep Llaveria、Penelope E. Streatfeild、Edward A. Anderson

  DOI：10.1021/acs.orglett.0c00089

  日期：2020.2.21

  Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama-Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations

  Resolvins D3和E1是解决炎症的重要信号分子。在这里，我们报告了一种收敛和灵活的策略，使用五元和六元环状烯基硅氧烷的Hiyama-Denmark偶联制备这些天然产物，以连接三个resolvin片段，并控制天然产物（Z）-烯烃的立体化学。这种方法的模块化性质使得能够合成新颖的RESOLVIN杂种，为进行RESOLVIN生物学的更广泛的研究提供了机会。
• Cyclic Sulfur Ylides Derived from Gleason-Type Chiral Auxiliaries for the Asymmetric Synthesis of Epoxy Amides
  作者：Francisco Sarabia、Carlos Vivar-García、Miguel García-Castro、Jorge Martín-Ortiz

  DOI：10.1021/jo1025964

  日期：2011.5.6

  Gleason-type chiral auxiliaries were used for the synthesis of a novel class of sulfonium salts, obtained via methylation of the sulfide with Meerwein's salt. The salts were reacted with aldehydes under basic conditions to provide epoxy amides, which were reduced to their corresponding epoxy alcohols in excellent enantiomeric excesses. Interestingly, it was feasible to synthesize both enantiomeric

  格里森型手性助剂用于合成一类新型的salts盐，该via盐是通过用Meerwein盐将硫化物甲基化而获得的。该盐在碱性条件下与醛反应，得到环氧酰胺，将其以优异的对映体过量还原为相应的环氧醇。有趣的是，它是合成两个对映异构体的环氧醇，这取决于所述锍盐的可行的，从制备升α-氨基酸（6和9从升-缬氨酸或15和16从升-丝氨酸）中的溶液使用。
• A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide
  作者：Francisco Sarabia、Samy Chammaa、Miguel García-Castro、Francisca Martín-Gálvez

  DOI：10.1039/b912070j

  日期：——

  A new type of chiral sulfur ylides has been synthesized and their reactivities against carbonyl compounds tested, showing a high degree of stereoselectivity in the formation of transepoxyamides under very mild reaction conditions.

  一种新型手性硫叶立德被合成，并测试了其对羰基化合物的反应活性，结果表明在非常温和的反应条件下，生成transepoxy酰胺具有高度的立体选择性。