(2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarbohydrazide | 1374018-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarbohydrazide
• CAS: 1374018-88-8
• 化学式: C₁₀H₁₈N₄O₄
• 分子量: 258.277
• InChiKey: JKXCPXQVPZQTDW-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarbohydrazide 、 氧化双(4-苯基异氰酸酯) 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到(4R,5R,25R,26R)-tetra-(hydrazinecarboxamide)cyclophane
  参考文献：
  名称：

  Synthesis of novel chiral tetra-(hydrazinecarboxamide) cyclophane macrocycles

  摘要：

  A novel class of chiral enantiomerically pure C-2-symmetric polyamide macrocycles has been synthesized from the reaction of chiral dioxolane dicarbohydrazides, obtained from commercially available tartaric acid, and aromatic diisocyanates. The novel macrocycles form in almost quantitative yields in a chemoselective [2+2]-cyclocondensation reaction under conformational bias of the dicarbohydrazides. The reaction takes place in anhydrous THF at a relatively high concentration of reactants without addition of external templates or application of high dilution conditions. The structures of the novel polyamide macrocycles were verified and fully assigned by H-1 NMR, C-13 NMR, 2D ROESY NMR, 2D HMBC, 2D HMQC, DEPT 135, FT IR, and CD spectroscopy. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.05.085
• 作为产物：
  描述：

  (2R,3R)-(–)-1,4-dioxaspiro[4.5]decane-2,3-dicarboxylic acid dimethyl ester 在 肼 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以90%的产率得到(2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarbohydrazide
  参考文献：
  名称：

  An expedient synthesis and conformational features of acylhydrazone macrocycles derived from tartaric acid: evidence of water and π aromatic hydrogen bond interactions

  摘要：

  Tartaric acid dihydrazides with acetal protected hydroxy groups react with terephthalaldehyde to preferentially form [2+2] bisacylhydrazone macrocycles. The structures of these macrocycles display all anti N-N and C=N bonds. Both trans- and cis-C(O)-NH bonds are present in the macrocycle thus allowing the formation of a rather compact macrocyclic structure. The structures of the acylhydrazone macrocycle are shown to be different in the crystal and in the isolated molecule due to the structure determining role of water included in the crystal lattice: in the former all of the O=C-C-H bonds are anti, while in the latter both syn- and anti-bonds are present. Both the non-planarity of the bisacylhydrazone molecules and their chiral interchromophoric interactions contribute to the rotatory power of the molecule. The low-temperature X-ray crystal structure of this compound provides direct evidence for hydrogen bonding between water and the aromatic pi-electrons in the solid state. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.02.010

文献信息

• Synthesis of novel chiral bis-N-substituted-hydrazinecarboxamide receptors and probing their solution-phase recognition to chiral carboxylic guests by ESI-TOF/MS and tandem ESI-MS
  作者：Hany F. Nour、Agnieszka Golon、Tuhidul Islam、Marcelo Fernández-Lahore、Nikolai Kuhnert

  DOI：10.1016/j.tet.2013.11.002

  日期：2013.12

  excellent yields by reacting chiral dicarbohydrazides, obtained from commercially available tartaric acid, with substituted aromatic isocyanates. The newly synthesized hydrazinecarboxamides formed structurally unique supramolecular aggregates, which have been confirmed by ESI-TOF/MS and tandem ESI-MS. They also showed molecular recognition to a selection of chiral carboxylic guests and oligopeptides, which

  通过使得自市售酒石酸的手性二碳酰肼与取代的芳族异氰酸酯反应，以良好至优异的产率合成了七个新颖的双-N-取代的肼基羧酰胺受体。新合成的肼甲酰胺形成了结构独特的超分子聚集体，这已由ESI-TOF / MS和串联ESI-MS证实。他们还显示了对手性羧酸客体和寡肽的选择的分子识别，它们模拟了细菌细胞壁的骨架结构。通过包括FTIR，1 H NMR，13 C NMR，ESI-TOF / MS，串联ESI-MS，2D ROESY NMR和CD光谱在内的各种光谱技术验证了新化合物的结构。