galactaric acid bishydrazide | 65978-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: galactaric acid bishydrazide
• 英文别名: (2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedihydrazide
• CAS: 65978-86-1
• 化学式: C₆H₁₄N₄O₆
• 分子量: 238.2
• InChiKey: YMIIBTMEYWGWGD-DUHBMQHGSA-N

物化性质

• 沸点：
  886.3±65.0 °C(Predicted)
• 密度：
  1.721±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  191
• 氢给体数：
  8
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  galactaric acid bishydrazide 在 亚硝酸 作用下， 生成 dimethyl galactarate
  参考文献：
  名称：

  Curtius, Journal fur praktische Chemie (Leipzig 1954), 1917, vol. <2> 95, p. 211

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S,4R,5S)-2,3,4,5-Tetrahydroxy-hexanedioic acid diethyl ester 在 乙醇 、 一水合肼 作用下， 生成 galactaric acid bishydrazide
  参考文献：
  名称：

  Curtius, Journal fur praktische Chemie (Leipzig 1954), 1917, vol. <2> 95, p. 211

  摘要：

  DOI：

文献信息

• First Synthesis of Double Headed 1,3,4‐Oxadiazino[6,5‐<i>b</i>]indole Acyclo<i>C</i>‐Nucleosides
  作者：Adel Z. Nasr

  DOI：10.1081/ncn-200040617

  日期：2004.1.12

  2‐dihydro‐2‐oxo‐1‐substituted‐3H‐indol‐3‐ylidene)hydrazides] (4b–d). Heterocyclization of the tetra‐O‐acetates 4b–d by heating with thionyl chloride afforded the double headed acyclo C‐nucleosides: 1,2,3,4‐tetra‐O‐acetyl‐1,4‐bis9‐substituted‐1,3,4‐oxadiazino[6,5‐b]indol‐2‐yl‐1‐ium}‐galacto‐tetritol dichlorides (5b–d). Structures of the prepared compounds were elucidated from their spectral properties.

  1,3-二氢-2,3-二氧代-2-H-吲哚（1a–c）与半乳糖酸双酰肼（2）缩合得到相应的半乳糖酸双[2-（1,2-1,2-二氢-2-氧代- [3H-吲哚-3-亚叉基]酰肼]（3a–c）。在吡啶存在下于室温下用乙酸酐对后一种化合物进行乙酰化，得到2,3,4,5-四-O-乙酰半乳糖酸双[2-（1,2-1,2-二氢-2-氧-氧-1-取代[-3H-吲哚-3-亚基）酰肼]（4b–d）。通过与亚硫酰氯一起加热使四邻乙酸酯4b–d杂环化，得到双头无环C-核苷：1,2,3,4-四邻乙酰基-1,4-双9-取代-1 ，3,4-恶二嗪[6,5-b]吲哚-2-基-1-基}-半乳糖-四糖醇二氯化物（5b-d）。从它们的光谱性质阐明了所制备化合物的结构。
• First Synthesis of Double Headed 1,2,4-Triazino[5,6-<i>b</i>]indole Acyclo<i>C</i>-Nucleosides
  作者：Adel Z. Nasr

  DOI：10.1002/jccs.200500075

  日期：2005.6

  one-nitrogen cyclizing agents gave the corresponding 1,4-bis1,2,4-triazino[5,6-b]indol-3-yl}-galacto-tetritols 4-8. Acetylation of the latter double headed acyclo C-nucleosides with acetic anhydride in the presence of pyridine at ambient temperature resulted in N- and O-acetylation to give the corresponding 1,2,3,4-tetra-O-acetyl-1,4-bis1,2,4-triazino[5,6-b]indol-3-yl}-galacto-tetritols 9-13 which were found

  双(2-氧代-吲哚-3-亚基)-半乳糖酰肼(3)与多种单氮环化剂杂环化得到相应的1,4-双1,2,4-三嗪[5,6 -b]indol-3-yl}-半乳糖四醇 4-8。后一种双头无环 C-核苷在环境温度下在吡啶存在下用乙酸酐乙酰化导致 N-和 O-乙酰化，得到相应的 1,2,3,4-四-O-乙酰-1,4 -bis1,2,4-triazino[5,6-b]indol-3-yl}-galacto-tetriitols 9-13 被发现存在于中心对称之字形构象中 20. 指定的结构得到了 1 的证实H, 1 3 C NMR以及质谱。
• Utilization of Dipotassium Salt of Galactaric Acid Bis(Hydrazidocarbodithioic Acid) As a Synthone for Double-Headed 1,3,4-Thiadiazoline, 1,3,4-Oxadiazoline and 1,2,4-Triazoline Acyclo C-Nucleosides
  作者：A. Z. Nasr、M. A. Mostafa

  DOI：10.1080/104265090888397

  日期：2005.8.1

  Condensation of galactaric acid bis hydrazide (1) with carbon disulfide in the presence of ethanolic potassium hydroxide gave the dipotassium salt of galactaric acid bis (hydrazidocarbodithioic acid) (2). Heterocyclization of the key compound 2 produced three different types of double headed acyclo C-nucleosides: acid-catalyzed dehydrative cyclization afforded the 5-thioxo-1,3,4-thiadiazoline 3, base-catalyzed dehydrosulfurative cyclization gave the 5-thioxo-1,3,4-oxadiazoline 5, and condensative cyclization with concomitant dehydrosulfuration and dehydration with different nitrogen nucleophiles yielded the 5-thioxo-1,2,4-triazolines 7 and 9a, b.Acetylation of the prepared acyclo C-nucleosides 3, 5, 7 and 9a, b with acetic anhydride in the presence of pyridine at ambient temperature caused acetylation of the sugar hydroxyls as well as heterocyclo imino protons to give the tetra-O-acetates 4, 6, and 10a, b, respectively. Representative members of the prepared compounds were tested for antimicrobial activity.
• US4401751A
  申请人：——

  公开号：US4401751A

  公开（公告）日：1983-08-30