[(2S,3S)-3-(4-methoxyphenyl)oxiran-2-yl]methanol | 931385-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2S,3S)-3-(4-methoxyphenyl)oxiran-2-yl]methanol
• CAS: 931385-40-9
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: WWEWCYHYHOYFKO-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-3-(4-methoxyphenyl)oxiran-2-yl]methanol 在 sodium azide 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以84%的产率得到(2R,3R)-3-Azido-3-(4-methoxy-phenyl)-propane-1,2-diol
  参考文献：
  名称：

  NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa

  摘要：

  The NaIO4-mediated asymmetric bromohydroxylation of alpha,beta-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral alpha-bromo-beta-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and L-threo-DOPS (droxidopa). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.109
• 作为产物：
  描述：

  [(4R)-2,2-dimethyl-4-(2-methylsulfanylethyl)-1,3-oxazolidin-3-yl]-[(2R,3S)-3-(4-methoxyphenyl)oxiran-2-yl]methanone 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到[(2S,3S)-3-(4-methoxyphenyl)oxiran-2-yl]methanol
  参考文献：
  名称：

  A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide

  摘要：

  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。

  DOI：

  10.1039/b912070j

文献信息

• 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。
• NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (−)-cytoxazone and droxidopa
  作者：Shyla George、Srinivasarao V. Narina、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2006.12.109

  日期：2007.2

  The NaIO4-mediated asymmetric bromohydroxylation of alpha,beta-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral alpha-bromo-beta-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and L-threo-DOPS (droxidopa). (c) 2007 Elsevier Ltd. All rights reserved.
• A Highly Stereoselective Synthesis of Glycidic Amides Based on a New Class of Chiral Sulfonium Salts: Applications in Asymmetric Synthesis
  作者：Francisco Sarabia、Carlos Vivar-García、Miguel García-Castro、Cristina García-Ruiz、Francisca Martín-Gálvez、Antonio Sánchez-Ruiz、Samy Chammaa

  DOI：10.1002/chem.201201332

  日期：2012.11.19

  A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α‐amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans‐epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The

  由α-氨基酸设计并合成了一种新型的具有双环体系特征的手性sulf盐。通过对treatment盐进行碱性处理而制备的它们相应的酰基化物，可与各种简单的手性醛平稳地反应，以合理至非常高的收率和出色的立体选择性（> 98％）提供反式环氧酰胺。发现获得的环氧酰胺可用作合成构件。因此，它们被还原成相应的环氧醇，并与不同类型的亲核试剂进行环氧乙烷开环反应。