trans-(R(S))-2-hydroxy-1-phenylethyl nitrate | 75561-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-(R(S))-2-hydroxy-1-phenylethyl nitrate
• 英文别名: (RS)-2-hydroxy-1-phenylethyl nitrate；1-phenyl-2-hydroxy-1-ethyl nitrate；1-hydroxy-2-phenylethyl nitrate；2-phenyl-2-nitratoethanol；(2-Hydroxy-1-phenylethyl) nitrate
• CAS: 75561-14-7
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: HJZAIMHRCPGGNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 trans-(R(S))-2-hydroxy-1-phenylethyl nitrate
  参考文献：
  名称：

  使用CAN的环氧化合物的硝酸酯衍生物：4-烷氧基三嗪合成中关键中间体的高效制备

  摘要：

  描述了在非质子溶剂中环氧化物与CAN（0.5当量）的区域和立体选择性打开反应。这种新颖的反应使得可以制备通用的硝酸酯衍生物，作为有用的中间体，用于合成在C-4位广泛取代的三叉戟。

  DOI：

  10.1016/s0040-4039(97)00670-9

文献信息

• Tetranitromethane as an efficient reagent for the conversion of epoxides into β-hydroxy nitrates
  作者：Yuliya A. Volkova、Olga A. Ivanova、Ekaterina M. Budynina、Elena B. Averina、Tamara S. Kuznetsova、Nikolai S. Zefirov

  DOI：10.1016/j.tetlet.2008.04.050

  日期：2008.6

  A convenient regioselective method for the preparation of β-hydroxy nitrates based on the ring opening reaction of epoxides by tetranitromethane in the presence of triethylamine is described. A series of substituted β-hydroxy nitrates were obtained in high yields under mild conditions.

  描述了一种方便的区域选择性方法，该方法基于在三乙胺存在下四硝基甲烷与环氧化物的开环反应制备β-羟基硝酸盐。在温和的条件下以高收率获得了一系列取代的β-羟基硝酸盐。
• Efficient Regio- and Stereoselective Conversions of Oxiranes and Aziridines intoβ-(Nitrooxy)-Substituted Alcohols and Amines by Using Bismuth Nitrate
  作者：Biswanath Das、Maddeboina Krishnaiah、Katta Venkateswarlu、Vtukuri Saidi Reddy

  DOI：10.1002/hlca.200790002

  日期：2007.1

  Oxiranes and aziridines efficiently undergo ring opening with bismuth nitrate at room temperature to furnish the corresponding β-(nitrooxy)-substituted alcohols and amines respectively. The conversions are highly regio- and stereoselective and afford the nitrooxy-compounds in excellent yields within a short period of time.

  环氧乙烷和氮丙啶在室温下通过硝酸铋有效地开环，分别提供相应的β-（硝基氧基）取代的醇和胺。所述转化是高度区域选择性和立体选择性的，并且在短时间内以优异的产率提供了硝基氧基化合物。
• Micellar media for the efficient ring opening of epoxides with CN–, N3–, NO3–, NO2–, SCN–, Cl– and Br– catalyzed with Ce(OTf)4
  作者：Nasser Iranpoor、Habib Firouzabadi、Marzieh Shekarize

  DOI：10.1039/b211697a

  日期：2003.2.11

  Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN−, N3−, NO3−, NO2−, SCN−, Br− and Cl−, catalyzed with Ce(OTf)4. This method is an efficient procedure for the synthesis of different β-substituted alcohols under mild reaction conditions. The reaction with SCN− is an easy procedure for the high yielding preparation of epoxy sulfides.

  引入胶束介质以高效地打开环氧化物，使用如CN⁻、N3⁻、NO3⁻、NO2⁻、SCN⁻、Br⁻和Cl⁻等亲核盐，并用Ce(OTf)₄催化。这种方法是在温和反应条件下合成不同β-取代醇的高效程序。与SCN⁻的反应是一种简单的程序，用于高产率制备环氧硫化物。
• Thallium nitrate as a reagent for the conversion of epoxides into α-hydroxynitrate esters and for the cleavage of aliphatic ethers
  作者：E. Mincione、F. Lanciano

  DOI：10.1016/s0040-4039(01)83936-8

  日期：——

  Simple as well as steroidal oxiranes are converted into the corresponding α-hydroxy nitrate esters by treatment with Tl(NO3)3 in hexane solution. Moreover aliphatic ethers react with Tl(NO3)3 in acetic anhydride via cleavage of the ethereal bond and formation of the corresponding acetoxy derivatives.

  通过在己烷溶液中用Tl（NO 3）3处理，将简单的以及甾族的环氧乙烷转化为相应的α-羟基硝酸酯。此外，脂族醚通过裂解醚键并形成相应的乙酰氧基衍生物而与乙酸酐中的Tl（NO 3）3反应。
• Iron(III) Trifluoroacetate as an Efficient Catalyst for Solvolytic and Nonsolvolytic Nucleophilic Ring Opening of Epoxides
  作者：Nasser Iranpoor、Hadi Adibi

  DOI：10.1246/bcsj.73.675

  日期：2000.3

  Iron(III) trifluoroacetate was used as an efficient and nonhygroscopic catalyst for the alcoholysis, hydrolysis, and acetolysis of epoxides. The addition of chloride, bromide, iodide, and nitrate ions to epoxides to produce the corresponding 2-halo and 2-nitratoalkanols and also the conversion of epoxides to acetonides and thiiranes were also performed efficiently in the presence of this catalyst.

  三氟乙酸铁（III）被用作一种高效且不吸湿的催化剂，用于环氧化物的醇解、水解和乙酰分解。在该催化剂的作用下，氯离子、溴离子、碘离子和硝酸根离子与环氧化物的加成反应可生成相应的 2-卤代烷醇和 2-硝基烷醇，环氧化物与丙酮和硫代烷烃的转化反应也可高效进行。

表征谱图