di-tert-butyl (S)-1-(1-amino-3-ethoxy-2-(4-fluorophenyl)-1,3-dioxopropan-2-yl)hydrazine-1,2-dicarboxylate | 1231929-54-6

• 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: di-tert-butyl (S)-1-(1-amino-3-ethoxy-2-(4-fluorophenyl)-1,3-dioxopropan-2-yl)hydrazine-1,2-dicarboxylate
• CAS: 1231929-54-6
• 化学式: C₂₁H₃₀FN₃O₇
• 分子量: 455.484
• InChiKey: CUPQMRHYZHLOKV-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  137.26
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  偶氮二甲酸二叔丁酯 、 ethyl 3-amino-2-(4-fluorophenyl)-3-oxopropanoate 在 lanthanum(III) nitrate hexahydrate 、 L-缬氨酸叔丁酯盐酸盐 、 (RS)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide 作用下， 以 乙酸乙酯 、 异丙醇 为溶剂， 反应 16.5h， 以95%的产率得到di-tert-butyl (S)-1-(1-amino-3-ethoxy-2-(4-fluorophenyl)-1,3-dioxopropan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Solvent-Dependent Self-Discrimination of Bis(2-hydroxyphenyl)diamides

  摘要：

  AbstractSolvent‐dependent, self‐discrimination of diamides is described. Mixing a solution of (R)‐1 a and (S)‐1 a, which are valine‐derived, bis(2‐hydroxyphenyl)diamide‐bearing, multiple hydrogen‐bonding modules, in dichloromethane immediately led to the formation of a thick suspension comprising a 1:1 heterochiral aggregate of 1 a. The solubility of heterochiral 1 a was substantially lower in halogenated solvents than in ethyl acetate. A perusal of racemic crystal structures obtained from chloroform and ethyl acetate revealed a significant difference in the crystal‐packing pattern, which is likely to be the basis for the pronounced difference in solubility. Specific self‐discrimination of 1 a in an ensemble of eight structurally related molecules showcased the specific aggregation through the hydrogen‐bonding network of the bis(2‐hydroxyphenyl)diamide framework. The low solubility of heterochiral 1 a in halogenated solvent was exploited to achieve high stereoselectivity in a catalytic asymmetric reaction by using a low enantiomeric excess sample of 1 a.

  DOI：

  10.1002/chem.201000321