2,5-diphthalimido-2,5-dideoxy-1,4:3,6-dianhydroiditol | 67870-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,5-diphthalimido-2,5-dideoxy-1,4:3,6-dianhydroiditol
• 英文别名: 2,5-diphthalimido-1,4;3,6-dianhydro-2,5-dideoxy-L-iditol；2,5-Diphthalimido-1,4;3,6-dianhydro-2,5-didesoxy-L-idit；2-[(3S,3aR,6S,6aR)-6-(1,3-dioxoisoindol-2-yl)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]isoindole-1,3-dione
• CAS: 67870-22-8
• 化学式: C₂₂H₁₆N₂O₆
• 分子量: 404.379
• InChiKey: LLRRIWWHIPROGV-WNRNVDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-diphthalimido-2,5-dideoxy-1,4:3,6-dianhydroiditol 在 乙醇 、 一水合肼 作用下， 生成 2,5-二氨基-1,4:3,6-二去氢-2,5-二脱氧己糖醇
  参考文献：
  名称：

  The Stereochemistry of 1,4: 3,6-Dianhydrohexitol Derivatives¹

  摘要：

  DOI：

  10.1021/ja01594a055
• 作为产物：
  描述：

  potassium phtalimide 、 1,4:3,6-dianhydro-2,5-bis-O-(methylsulfonyl)-D-mannitol 以 二甲基亚砜 为溶剂， 反应 24.0h， 以75%的产率得到2,5-diphthalimido-2,5-dideoxy-1,4:3,6-dianhydroiditol
  参考文献：
  名称：

  Chiral building blocks from biomass: 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol

  摘要：

  An efficient route towards the synthesis of 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol 4 has been developed resulting in significant improvements in both isolated yields and purity when compared to literature procedures. As a consequence, resin-grade 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol 4 has become available for laboratory scale step-growth polymer synthesis. Additionally, an interesting renewable chiral 2-amino-2-deoxy-1,4-3,6-dianhydroiditol 10, has been isolated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.031

文献信息

• Partially bio-based polyimides from isohexide-derived diamines
  作者：Xiaodong Ji、Zikun Wang、Jingling Yan、Zhen Wang

  DOI：10.1016/j.polymer.2015.07.051

  日期：2015.9

  Novel partially bio-based polyimides were prepared from 2, 5-diamino-2, 5-dideoxy-1, 4: 3, 6-dianhydrosorbitol (diaminoisosorbide, DAIS) dihydrochloride, 2, 5-diamino-2, 5-dideoxy-1, 4: 3, 6-dianhydroiditol (diaminoisoidide, DAII) dihydrochloride, and various dianhydrides via a conventional one-step method in m-cresol. Inherent viscosity values of these polyimides spanned a range of 0.5 -1.5 dL/g. Flexible and transparent films can be easily cast from their corresponding solutions. The chemical structures and properties of isohexide-derived polyimides were fully characterized by using a variety of analytical techniques. The results revealed that the thermal and mechanical properties of isohexide-derived polyimides were similar to those derived from petrochemical-based diamines. Moreover, these polyimides exhibited good optical transparency, and optical activity. The good overall properties of isohexide-derived polyimides can be contributed to the incorporation of unique isohexide moieties that were rigid, thermally stable, fully aliphatic and chiral. (C) 2015 Elsevier Ltd. All rights reserved.
• The Stereochemistry of 1,4: 3,6-Dianhydrohexitol Derivatives¹
  作者：Arthur C. Cope、T. Y. Shen

  DOI：10.1021/ja01594a055

  日期：1956.7
• Chiral building blocks from biomass: 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol
  作者：Shanmugam Thiyagarajan、Linda Gootjes、Willem Vogelzang、Jing Wu、Jacco van Haveren、Daan S. van Es

  DOI：10.1016/j.tet.2010.11.031

  日期：2011.1

  An efficient route towards the synthesis of 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol 4 has been developed resulting in significant improvements in both isolated yields and purity when compared to literature procedures. As a consequence, resin-grade 2,5-diamino-2,5-dideoxy-1,4-3,6-dianhydroiditol 4 has become available for laboratory scale step-growth polymer synthesis. Additionally, an interesting renewable chiral 2-amino-2-deoxy-1,4-3,6-dianhydroiditol 10, has been isolated. (C) 2010 Elsevier Ltd. All rights reserved.