(Z)-2-hydroxy-3-(4-nitrophenyl)-propenal | 116204-36-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (Z)-2-hydroxy-3-(4-nitrophenyl)-propenal
• 英文别名: (Z)-2-hydroxy-3-(4-nitrophenyl)prop-2-enal
• CAS: 116204-36-5
• 化学式: C₉H₇NO₄
• 分子量: 193.159
• InChiKey: VKDMHVGBEQABHB-UITAMQMPSA-N

物化性质

• 熔点：
  173-175 °C
• 沸点：
  386.4±42.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-hydroxy-3-(4-nitrophenyl)-propenal 在 3 A molecular sieve 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 Acetic acid (Z)-1-dimethoxymethyl-2-(4-nitro-phenyl)-vinyl ester
  参考文献：
  名称：

  Selective Protection of the Functionalities of α-Hydroxy Unsaturated Aldehydes

  摘要：

  多官能化的标题化合物δ-烯醇醛可选择性地以乙烯醛乙酸酯、乙烯醛磺酸盐、乙烯缩醛磺酸盐或氧代缩醛衍生物的形式进行保护。

  DOI：

  10.1055/s-1994-25652
• 作为产物：
  描述：

  (Z)-2-methoxy-3-(4-nitrophenyl)propenal 在 盐酸 、 水 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以56%的产率得到(Z)-2-hydroxy-3-(4-nitrophenyl)-propenal
  参考文献：
  名称：

  Hydrolysis of (Z)-2-alkoxy-3-arylpropenals as a short-cut to benzylglyoxals

  摘要：

  Hydrolysis of the C=C bond in 2-alkoxy-3-aryl(hetaryl)propenals, depending upon substituents in the molecule, can proceed according to Markovnikov or Michael rule or with heterolytic opening of the cycle (in the case of 2-alkoxy-3-furylpropenal). Hydrolysis of 3-phenyl substituted alkoxypropenals bearing electron-withdrawing substituents (Cl, NO2) in the p-position has allowed a method for the preparation of corresponding benzylglyoxals (stable in enol form) to be developed.

  DOI：

  10.1016/j.mencom.2016.09.023

文献信息

• A simple and direct synthesis of α-hydroxy unsaturated aldehydes from α-cyano-α-hydroxymethyl epoxides
  作者：Layachi Khamliche、Albert Robert

  DOI：10.1039/c39870001869

  日期：——

  The ring opening of α-cyano-α-hydroxymethyl epoxides by a solution of the complex Li2NiBr4 in tetrahydrofuran leads to α-bromo-α′-hydroxy ketones which in treatment with pyridine give good yields of α-hydroxy unsaturated aldehydes.

  通过配合物Li 2 NiBr 4在四氢呋喃中的溶液使α-氰基-α-羟甲基环氧化物开环，得到α-溴-α'-羟基酮，用吡啶处理可得到良好产率的α-羟基不饱和醛。
• Synthèse de cétones α, α′-fonctionnalisées puis d'aldéhydes α-énols par ouverture des α-cyano α-hydroxyméthyl époxydes.
  作者：K. Layachi、I. Ariès-Gautron、M. Guerro、A. Robert

  DOI：10.1016/s0040-4020(01)88717-2

  日期：1992.2

  Two synthetic routes to alpha-enol aldehydes are described. Monosubstituted alpha-enol aldehydes are obtained via Li2NiBr4/THF, ring opening of the trisubstituted alpha-cyano alpha-hydroxymethyl epoxides while disubstituted alpha-enol aldehydes are prepared through HX opening of the corresponding tetrasubstituted epoxide alcohols protected as acetate, followed by Ni(OAc)2 decyanation of the intermediate cyanhydrins and by NaOAc deprotection of the formed alpha,alpha'-functionalized ketones.
• KHAMLICHE, LAYACHI;ROBERT, ALBERT, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 24, 1869-1870
  作者：KHAMLICHE, LAYACHI、ROBERT, ALBERT

  DOI：——

  日期：——
• Selective Protection of the Functionalities of α-Hydroxy Unsaturated Aldehydes
  作者：L. Khamliche、S. Bakkas、A. Robert

  DOI：10.1055/s-1994-25652

  日期：——

  The polyfunctionalized title compounds α-enol aldehydes are selectively protected either as ethylenic aldehyde acetates, ethylenic aldehyde sulfonates, ethylenic acetal sulfonates, or oxo acetal derivatives.

  多官能化的标题化合物δ-烯醇醛可选择性地以乙烯醛乙酸酯、乙烯醛磺酸盐、乙烯缩醛磺酸盐或氧代缩醛衍生物的形式进行保护。
• Hydrolysis of (Z)-2-alkoxy-3-arylpropenals as a short-cut to benzylglyoxals
  作者：Natalia A. Keiko、Nadezhda V. Vchislo、Ekaterina A. Verochkina、Yurii A. Chuvashev、Lyudmila I. Larina

  DOI：10.1016/j.mencom.2016.09.023

  日期：2016.9

  Hydrolysis of the C=C bond in 2-alkoxy-3-aryl(hetaryl)propenals, depending upon substituents in the molecule, can proceed according to Markovnikov or Michael rule or with heterolytic opening of the cycle (in the case of 2-alkoxy-3-furylpropenal). Hydrolysis of 3-phenyl substituted alkoxypropenals bearing electron-withdrawing substituents (Cl, NO2) in the p-position has allowed a method for the preparation of corresponding benzylglyoxals (stable in enol form) to be developed.