2-methyl-3-(4-fluorophenyl)-1,3-propane diol | 928840-61-3

• 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: 2-methyl-3-(4-fluorophenyl)-1,3-propane diol
• 英文别名: 1-(4-Fluorophenyl)-2-methylpropane-1,3-diol
• CAS: 928840-61-3
• 化学式: C₁₀H₁₃FO₂
• 分子量: 184.21
• InChiKey: VVYOUSHUOIDWOX-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：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(4-fluorophenyl)-1,3-propane diol 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 3.0h， 以83%的产率得到1-(4-氟-苯基)-丙烷-1,2-二酮
  参考文献：
  名称：

  2-碘氧基苯甲酸通过 CC 键的氧化裂解介导 1,3-二醇轻松转化为 1,2-二酮

  摘要：

  1,3-二醇在 2-碘氧基苯甲酸 (IBX) 存在下顺利氧化裂解 CC 键，在温和条件下以优异的产率生成 1,2-二酮。

  DOI：

  10.1055/s-2006-950372
• 作为产物：
  描述：

  3-(4-fluorophenyl)-3-hydroxy-2-methylpropanal 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 syn-1-(4-fluorophenyl)-2-methylpropane-1,3-diol 、 2-methyl-3-(4-fluorophenyl)-1,3-propane diol 、 (1S,2R)-1-(4-fluorophenyl)-2-methylpropane-1,3-diol
  参考文献：
  名称：

  Chiral Primary Amine Organocatalysts for Syn-selective Asymmetric Cross-Aldol Reactions

  摘要：

  Based on the "acid-base" interaction strategy, organocatalysts for the asymmetric cross-aldol reaction were synthesized by the in situ combination of chiral primary amines with protonic acids. Unlike general secondary amine catalysts that give anti-selective products, as-prepared primary amine catalysts can give syn-selcctive cross-aldol products with high yield and high selectivity (up to 90% yield, 90:10 syn/anti ratio, 90% ee). Compared with the complex synthesis of the reported catalysts, the primary amine catalyst that gave the best results was easily prepared using commercial available (1S,2S)-(+)-cyclohexanediamine.

  DOI：

  10.1016/s1872-2067(10)60237-9

文献信息

• Domino Hydroformylation/Enantioselective Cross-Aldol Addition
  作者：Olivier Abillard、Bernhard Breit

  DOI：10.1002/adsc.200700216

  日期：2007.8.6

  A domino hydroformylation/enantioselective cross-aldol reaction sequence is reported. Starting from simple alkenes enantiomerically pure aldol addition products, which represent valuable building blocks for polypropionate construction, can be obtained in a one-pot operation.

  报道了多米诺加氢甲酰化/对映选择性交叉羟醛反应序列。从简单的烯烃开始，对映体纯的羟醛加成产物可以代表一锅操作，代表了丙酸酯构建的重要组成部分。
• 2-Iodoxybenzoic Acid Mediated Facile Conversion of 1,3-Diols to 1,2-Diketones by Oxidative Cleavage of the C-C Bond
  作者：J. Yadav、Swapan Biswas、R. Srinivas

  DOI：10.1055/s-2006-950372

  日期：——

  1,3-Diols undergo smooth oxidative cleavage of the C-C bond in the presence of 2-iodoxybenzoic acid (IBX) affording 1,2-diketones in excellent yields under mild conditions.

  1,3-二醇在 2-碘氧基苯甲酸 (IBX) 存在下顺利氧化裂解 CC 键，在温和条件下以优异的产率生成 1,2-二酮。
• Chiral Primary Amine Organocatalysts for Syn-selective Asymmetric Cross-Aldol Reactions
  作者：Qiang GAO、Yan LIU、Shengmei LU、Can LI

  DOI：10.1016/s1872-2067(10)60237-9

  日期：2011.1

  Based on the "acid-base" interaction strategy, organocatalysts for the asymmetric cross-aldol reaction were synthesized by the in situ combination of chiral primary amines with protonic acids. Unlike general secondary amine catalysts that give anti-selective products, as-prepared primary amine catalysts can give syn-selcctive cross-aldol products with high yield and high selectivity (up to 90% yield, 90:10 syn/anti ratio, 90% ee). Compared with the complex synthesis of the reported catalysts, the primary amine catalyst that gave the best results was easily prepared using commercial available (1S,2S)-(+)-cyclohexanediamine.