methyl 2,2-dichloro-3-hydroxy-3-phenylpropanoate | 16715-03-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 2,2-dichloro-3-hydroxy-3-phenylpropanoate
• 英文别名: methyl 2,2-dichloro-3-hydroxy-3-phenylpropionate；methyl 2,2-dichloro-3-hydroxy-3-phenylpropenoate；2,2-Dichlor-3-hydroxy-3-phenyl-propionsaeure-methylester
• CAS: 16715-03-0
• 化学式: C₁₀H₁₀Cl₂O₃
• 分子量: 249.094
• InChiKey: UKKPUIWLJZJEJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,2-dichloro-3-hydroxy-3-phenylpropanoate 在 lithium dimethylcuprate 作用下， 以 乙醚 为溶剂， 生成 methyl 2-chloro-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Action du dimethylcuprate de lithium sur les composés carbonylés α,α-dichlorés

  摘要：

  DOI：

  10.1016/s0022-328x(00)86598-5
• 作为产物：
  描述：

  二氯乙酸甲酯 、 苯甲醛 在 三氯乙酸甲酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以48%的产率得到methyl 2,2-dichloro-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Electroorganic chemistry. 88. Chain reactions induced by cathodic reduction

  摘要：

  DOI：

  10.1021/jo00214a025

文献信息

• Addition of halogenoacetic esters to aldehydes and ketones in the presence of Fe(CO)5
  作者：A. B. Terentiev、T. T. Vasilieva、N. A. Kuz'mina、O. V. Chakhovskaya、E. S. Brodsky、Yu. N. Belokon'

  DOI：10.1007/bf02495489

  日期：2000.4

  The use of complex-forming solvents and variations in the reaction temperature made it possible to prepare α-halogeno β-hydroxy carboxylic esters upon addition of halogenoacetic esters to aldehydes and ketones promoted by iron pentacarbonyl.

  使用形成络合物的溶剂和改变反应温度使得在五羰基铁促进下将卤代乙酸酯加成到醛和酮中制备 α-卤代 β-羟基羧酸酯成为可能。
• Synthesis of dihalohydrins and tri- and tetra-substituted olefins
  申请人：Board of Regents, The University of Texas System

  公开号：US20040143125A1

  公开（公告）日：2004-07-22

  A novel synthesis reaction for highly stereospecific tri- and tetra-substituted olefins is described. A single stereoisomer of stable &agr;-halo-&agr;,&bgr;-ester is produced in high yield by the reaction of aldehyde or ketone with a trihalogenated compound such as trichloroacetate in the presence of CrCl 2 in a solvent. By varying the amount of CrCl 2 used, the stable dihalohydrin intermediate may be obtained as well.

  描述了一种用于高度立体特异性三取代和四取代烯烃的新合成反应。通过醛或酮与三卤代化合物（如三氯乙酸盐）在溶剂中在CrCl2存在下的反应，可以高产率地产生稳定的α-卤代-α，β-酯的单立体异构体。通过改变使用的CrCl2量，也可以获得稳定的二卤水合物中间体。
• ——
  作者：A. B. Terent'ev、T. T. Vasil'eva、N. A. Kuz'mina、N. E. Mysova、O. V. Chakhovskaya

  DOI：10.1023/a:1013175403637

  日期：——

  Pentacarbonyliron promotes addition of alpha-halocarboxylic acid esters at the carbonyl group of benzaldehyde and its para-substituted analogs. The substituent in the benzene ring strongly affects the process.
• A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine–bromine complexes
  作者：Zhen-Wu Mei、Takumi Omote、Mounir Mansour、Hiroyuki Kawafuchi、Yutaka Takaguchi、Anny Jutand、Sadao Tsuboi、Tsutomu Inokuchi

  DOI：10.1016/j.tet.2008.08.051

  日期：2008.11

  A new TEMPO-mediated catalytic oxidation method in combination with Py center dot HBr3 (stoichiometric) is developed for oxidation of secondary alcohols to the corresponding ketones. The performance of this oxidizing system is better compared with that of TEMPO method combined with R4NBr3 center dot Poly(4-vinylpyridine) HBr3 can be used in place of Py center dot HBr3. The electron-withdrawing substituent at the C-4 position of TEMPO increases the reactivity of TEMPO significantly in the oxidation of electron-deficient alcohols Such as polyhaloalkylmethanols. Inductive effect of the substituent of TEMPO is discussed through the characterization of the redox potential of N-O radical by cyclic voltammetry. (C) 2008 Elsevier Ltd. All rights reserved.
• Hayon, Annie-Flore; Fehrentz, Jean-Alain; Chapleur, Yves, Bulletin de la Societe Chimique de France, 1983, vol. 2, # 7-8, p. 207 - 210
  作者：Hayon, Annie-Flore、Fehrentz, Jean-Alain、Chapleur, Yves、Castro, Bertrand

  DOI：——

  日期：——