(16R,21R)-1,9,15,22-tetrazapentacyclo[22.3.1.13,7.19,13.016,21]triaconta-3(30),4,6,10,13(29),24(28),26-heptaene-14,23-dione | 142959-85-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (16R,21R)-1,9,15,22-tetrazapentacyclo[22.3.1.13,7.19,13.016,21]triaconta-3(30),4,6,10,13(29),24(28),26-heptaene-14,23-dione
• CAS: 142959-85-1
• 化学式: C₂₆H₃₀N₄O₂
• 分子量: 430.55
• InChiKey: MJQXEZSUYLDYOO-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氯化烟碱盐酸盐 在 吡啶 、 sodium dithionite 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.33h， 生成 (16R,21R)-1,9,15,22-tetrazapentacyclo[22.3.1.13,7.19,13.016,21]triaconta-3(30),4,6,10,13(29),24(28),26-heptaene-14,23-dione
  参考文献：
  名称：

  Stereoselective reductions with macrocyclic NADH models

  摘要：

  Macrocyclic NADH models with two (C-2 symmetry) or four (D-2 symmetry) nicotinamide units comprised in a ring have been prepared and found to reduce activated carbonyl compounds in good yields and high enantiomeric excess. The roles of magnesium ions as a cocatalyst and the temperature have also been investigated. The smaller, C-2-symmetric macrocycle gave 96% ee upon reduction of ethyl benzoylformate whereas the best result with the larger D-2-symmetric model was 81% ee for the reduction of methyl benzoylformate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00248-2

文献信息

• Zinc meso-tetraphenylporphyrin as shift reagent for NADH-models
  作者：Klas Skog、Olof Wennerström

  DOI：10.1016/s0040-4020(01)85304-7

  日期：1994.1

  By the use of zinc meso-tetraphenylporphyrin as a shift reagent the conformations of two new NADH-models have been determined. Induced H-1-NMR shifts up to five ppm have been observed. The conformations determined in this study are consistent with theoretical calculations and NOE-measurements. It has been proven that zinc, which is a co-catalyst in the reduction of activated carbonyl compounds with NADH-models, coordinates to the oxygen of the amide groups in two of our model compounds.
• Antarafacial hydride transfer in a new chiral NADH model with C2-symmetry
  作者：Klas Skog、Olof Wennerström

  DOI：10.1016/s0040-4039(00)91724-6

  日期：1992.3

  A C2-symmetric macrocyclic NAD+/NADH-model, 1, in which hydride transfer occurs in an antarafacial way, has been prepared. On reduction of methyl benzoylformate with 1, methyl mandelate is formed in 95% ee.
• Stereoselective reductions with macrocyclic NADH models
  作者：Ulrik Gran、Olof Wennerström、Gunnar Westman

  DOI：10.1016/s0957-4166(00)00248-2

  日期：2000.7

  Macrocyclic NADH models with two (C-2 symmetry) or four (D-2 symmetry) nicotinamide units comprised in a ring have been prepared and found to reduce activated carbonyl compounds in good yields and high enantiomeric excess. The roles of magnesium ions as a cocatalyst and the temperature have also been investigated. The smaller, C-2-symmetric macrocycle gave 96% ee upon reduction of ethyl benzoylformate whereas the best result with the larger D-2-symmetric model was 81% ee for the reduction of methyl benzoylformate. (C) 2000 Elsevier Science Ltd. All rights reserved.