N,N'-dibenzyl-N,N'-ethylenetartramide | 112897-01-5

• 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: N,N'-dibenzyl-N,N'-ethylenetartramide
• 英文别名: (R,R)-N,N'-Dibenzyl-N,N'-ethylenetartramide；(6R,7R)-1,4-dibenzyl-6,7-dihydroxy-1,4-diazocane-5,8-dione
• CAS: 112897-01-5
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: KRWOCFGDPHLIFQ-QZTJIDSGSA-N

物化性质

• 熔点：
  202-203 °C
• 沸点：
  645.9±55.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.08
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N'-dibenzyl-N,N'-ethylenetartramide 在 Rh/Al₂O₃ 氢气 作用下， 以 乙醇 为溶剂， 以90%的产率得到(R,R)-N,N'-Bis(cyclohexylmethyl)-N,N'-ethylenetartramide
  参考文献：
  名称：

  N,N'-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide: An Improved Chiral Auxiliary for the Asymmetric Allylboration Reaction

  摘要：

  N,N-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide (8), synthesized by a simple four-step sequence from ethylenediamine and benzylidenetartaric acid, was designed in anticipation that the derived allylboronates 9-11 would display enhanced reactivity owing to the inductive effect of the N-trifluoroethyl substituents that would increase the Lewis acidity of the boron atom of the B-allyl-1,3,2-dioxaborolanes. Reagents 9-11 were synthesized by transesterification of 8 with the crystalline and easily purified allylboronate diethanolamine complexes 13, 19, and 25. Allylboronate 9 is ca. 100-fold more reactive than 6 and is also substantially more useful than the previously reported allyboronate 4, which suffers from very poor solubility in toluene at -78 degrees C. Most importantly, allylboronates 9-11 are significantly more enantioselective than the parent tartrate allylboronates 1-3 and rank among the most highly enantioselective allylboron reagents yet reported. Reactions of 9-11 with aldehydes are performed in THF at- -78 or -55 degrees C for 5-12 h periods. The enantioselectivity realized in reactions with achiral aldehydes is 92-95% ee (Table 2), and excellent diastereoselectivity is achieved in double asymmetric reactions with chiral aldehydes 15a, 15b, and 33 (Tables 3 and 4). For example, 16 and 28 are now available with a minimum selectivity of 92% from reactions of 15a and 15b with allylboronate 9, while the crotylboration products 29, 30, and 31 are available with a minimum selectivity of 90% (usually greater than or equal to 95%) from reactions of 15a and 15b with crotylboronates 10 and 11; the fourth isomer, 32a, is available with 83% selectivity. Chiral reagents 9-11 thus appear well suited for application to complex problems in organic synthesis.

  DOI：

  10.1021/jo00117a036
• 作为产物：
  描述：

  2,3-O-苄烯酒石酸二甲酯 以 水 、 溶剂黄146 为溶剂， 反应 17.0h， 以87%的产率得到N,N'-dibenzyl-N,N'-ethylenetartramide
  参考文献：
  名称：

  N,N'-二苄基-N,N'-乙撑酒石酰胺：一种合理设计的烯丙基硼化反应手性助剂

  摘要：

  Reaction du compose du titre avec des propanals, cyclohexanals et benzaldehyde: obtention d'alcools homoallyliques

  DOI：

  10.1021/ja00220a041

文献信息

• ROUSH, WILLIAM R.;BANFI, LUCA, J. AMER. CHEM. SOC., 110,(1988) N 12, 3979-3982
  作者：ROUSH, WILLIAM R.、BANFI, LUCA

  DOI：——

  日期：——