4,5,9,10-tetrahydro-4,9-methanodithieno[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarbaldehyde | 500100-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 4,5,9,10-tetrahydro-4,9-methanodithieno[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarbaldehyde
• 英文别名: 5,12-Dithia-1,8-diazatetracyclo[6.6.1.02,6.09,13]pentadeca-2(6),3,9(13),10-tetraene-4,11-dicarbaldehyde
• CAS: 500100-81-2
• 化学式: C₁₃H₁₀N₂O₂S₂
• 分子量: 290.367
• InChiKey: VNBVBPPIOKCLMO-UHFFFAOYSA-N

物化性质

• 沸点：
  598.7±50.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5,9,10-tetrahydro-4,9-methanodithieno[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarbaldehyde 在 三正丁基氢锡 作用下， 以 甲醇 为溶剂， 以75%的产率得到(5H,10H-4,9-methanodithieno[3,2-b:3',2'-f][1,5]diazocine-2,7-diyl)dimethanol
  参考文献：
  名称：

  Regio/diastereo-controls of the Bingel-type biscyclopropanation of [60]fullerene by using bismalonates with a Tröger base analogue-derived tether

  摘要：

  Four kinds of bismalonates tethered with a Troger base derivative were synthesized and used for the double Bingel reaction of [60]fullerene. the regio/diastereoselectivities of the reaction were highly influenced by the structure of the Troger base derivatives. Heteroaromatic analogues of the Troger base were found to be applicable as the core the the tether. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.022
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 4,5,9,10-tetrahydro-4,9-methanodithieno[3,2-b:3',2'-f][1,5]diazocine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以59%的产率得到4,5,9,10-tetrahydro-4,9-methanodithieno[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarbaldehyde
  参考文献：
  名称：

  Synthesis and functionalization of thiophene congeners of Tröger's base

  摘要：

  特罗格氏碱的噻吩同系物是通过 3-氨基噻吩和甲醛反应制备的。用 BuLi 或 LDA 处理噻吩同系物后，可在 2 位和 7 位上区域选择性地形成二元离子，并与三甲基氯硅烷、碘、NBS、DMF、二苯甲酮和苯甲醛等多种亲电体发生反应。这一反应为特罗格氏碱骨架与各种官能团的结合开辟了一条简便而多用途的途径。

  DOI：

  10.1039/b205227j

文献信息

• Synthesis and functionalization of thiophene congeners of Tröger's base
  作者：Tomoshige Kobayashi、Takashi Moriwaki、Masaya Tsubakiyama、Shihori Yoshida

  DOI：10.1039/b205227j

  日期：——

  Thiophene congeners of Tröger's base were prepared by the reactions of 3-aminothiophenes and formaldehyde. Treatment of the thiophene congeners with BuLi or LDA resulted in the regioselective formation of the dianion at the 2- and 7-positions, which reacted with a variety of electrophiles such as trimethylsilyl chloride, iodine, NBS, DMF, benzophenone, and benzaldehyde. This reaction opens up a facile and versatile entry for a Tröger's base skeleton with a variety of functional groups.

  特罗格氏碱的噻吩同系物是通过 3-氨基噻吩和甲醛反应制备的。用 BuLi 或 LDA 处理噻吩同系物后，可在 2 位和 7 位上区域选择性地形成二元离子，并与三甲基氯硅烷、碘、NBS、DMF、二苯甲酮和苯甲醛等多种亲电体发生反应。这一反应为特罗格氏碱骨架与各种官能团的结合开辟了一条简便而多用途的途径。
• A New Molecular Receptor Based on Thiophene Congener of Tröger’s Base: Selective Binding with Aliphatic and Aromatic Dicarboxylic Acids
  作者：Tomoshige Kobayashi、Takashi Moriwaki

  DOI：10.3987/com-03-s(p)28

  日期：——

  A new molecular receptor bearing pyridylamino groups was prepared with a thiophene congener of Troger's base as a spacer, and was found to exhibit selective binding toward aliphatic and aromatic dicarboxylic acids, primarily depending on the length of the carbon chain.

  用 Troger 碱的噻吩同系物作为间隔物制备了一种新的带有吡啶氨基的分子受体，发现其对脂肪族和芳香族二羧酸具有选择性结合，主要取决于碳链的长度。
• Regio/diastereo-controls of the Bingel-type biscyclopropanation of [60]fullerene by using bismalonates with a Tröger base analogue-derived tether
  作者：Yasuhiro Ishida、Hiroshi Ito、Daisuke Mori、Kazuhiko Saigo

  DOI：10.1016/j.tetlet.2004.11.022

  日期：2005.1

  Four kinds of bismalonates tethered with a Troger base derivative were synthesized and used for the double Bingel reaction of [60]fullerene. the regio/diastereoselectivities of the reaction were highly influenced by the structure of the Troger base derivatives. Heteroaromatic analogues of the Troger base were found to be applicable as the core the the tether. (C) 2004 Elsevier Ltd. All rights reserved.