triethyl trindane-2,5,8-tricarboxylate | 410074-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: triethyl trindane-2,5,8-tricarboxylate
• 英文别名: triethyl 2,3,4,5,6,7,8,9-octahydro-1H-cyclopenta[e]-as-indacene-2,5,8-tricarboxylate
• CAS: 410074-24-7
• 化学式: C₂₄H₃₀O₆
• 分子量: 414.499
• InChiKey: SIUIQJJACAWQGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  triethyl trindane-2,5,8-tricarboxylate 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 cis,cis,cis-2,5,8-tribenzyltrindane-2,5,8-tricarboxylic acid
  参考文献：
  名称：

  Choi, Heung-Jin; Park, Yeon Sil; Yun, Seok Hun, Organic letters, 2002, vol. 4, # 5, p. 795 - 798

  摘要：

  DOI：
• 作为产物：
  描述：

  trindane-2,2,5,5,8,8-hexacarboxylic acid 在 吡啶 、 硫酸 作用下， 反应 8.0h， 生成 triethyl trindane-2,5,8-tricarboxylate
  参考文献：
  名称：

  Choi, Heung-Jin; Park, Yeon Sil; Yun, Seok Hun, Organic letters, 2002, vol. 4, # 5, p. 795 - 798

  摘要：

  DOI：

文献信息

• Diastereofacial-Selective Synthesis of the Trindane-Based Molecular Scaffold <i>cis</i>,<i>cis</i>,<i>cis</i>-2,5,8-Tribenzyltrindane-2,5,8-tricarboxylate and an Arylamine Analogue for the Construction of <i>C</i>₃_v-Symmetric Architectures
  作者：Heung-Jin Choi、Jie Song、Chan An、Quoc-Thiet Nguyen、Hong-Seok Kim

  DOI：10.1055/s-2007-990828

  日期：2007.11

  Efficient syntheses of potentially valuable C 3 v -symmetric trindane-based triester scaffolds are reported. In the synthesis of 2,5,8-tribenzyltrindane-2,5,8-tricarboxylate by the benzylation of the corresponding triester by treatment with lithium diisopropyl­amide in tetrahydrofuran, the diastereoselectivity and yield of the cis,cis,cis- and cis,trans,trans-isomers depended primarily on the reaction temperature and the amount of hexamethylphosphoramide used as additive. High diastereofacial selectivity was achieved at -90 °C in tetrahydrofuran, and the cis,cis,cis-isomer was obtained as the major product in 45% yield and in a diastereomeric ratio of 1.12. Under the same reaction conditions the 2,5,8-tris(4-bromobenzyl)trindane-2,5,8-tricarboxylate analogue was synthesized in 46% yield; it was efficiently converted into the 2,5,8-tris(4-aminobenzyl)trindane-2,5,8-tricarboxylate by palladium-catalyzed aromatic C-N bond formation by reaction with hexamethyldisilazide as nitrogen source in the presence of bis(dibenzylideneacetone)palladium with tri-tert-butylphosphine as catalyst in toluene.

  报告了具有潜在价值的 C 3 v - 不对称茚满基三酯支架的高效合成。在四氢呋喃中用二异丙基酰胺锂处理相应的三酯，通过苄基化合成 2,5,8-三苄基三茚满-2,5,8-三羧酸酯时，顺式、顺式、顺式和顺式、反式、反式异构体的非对映选择性和产率主要取决于反应温度和用作添加剂的六甲基磷酰胺的用量。在-90 °C的四氢呋喃中实现了较高的非对映选择性，并以 45% 的产率和 1.12 的非对映比率获得了顺式、顺式、顺式异构体作为主要产物。在相同的反应条件下，合成了 2,5,8-三（4-溴苄基）茚满-2,5,8-三羧酸类似物，收率为 46%；在双(二苄基亚丙酮)钯存在下，以三叔丁基膦为催化剂，在甲苯中以六甲基二硅氮化物为氮源，通过钯催化芳香族 C-N 键的形成，有效地将其转化为 2,5,8-三(4-氨基苄基)茚满-2,5,8-三羧酸酯。
• C3-Symmetric tripodal nitrophenylurea based anion receptors built on structurally preorganized trindane scaffold
  作者：Yeon Sil Park、So-Hee Bang、Heung-Jin Choi

  DOI：10.1016/j.tetlet.2013.09.075

  日期：2013.12

  C-3v-Symmetric tripodal anion receptors with three urea or thiourea recognition motifs were synthesized from C-3v-symmetric cis,cis,cis-2,5,9-tri-p-bromobenzyltrindane molecular skeleton via Hartwig amination and then formation of urea compounds with the corresponding isocyanate. The anion receptors recognized halide and oxo anions with C-3-symmetry through the hydrogen bonding interactions between anions and the NH protons of urea or thiourea groups. The receptors 2 and 3 showed a significant binding affinity toward H2PO4- in DMSO-d(6); 392 and 305 M-1,respectively. The strong affinity of H2PO4- anion may be attributed to its tetrahedral geometry and the basicity of H2PO4- anion, allowing it to form stronger hydrogen-bonding. (C) 2013 Elsevier Ltd. All rights reserved.
• Choi, Heung-Jin; Park, Yeon Sil; Yun, Seok Hun, Organic letters, 2002, vol. 4, # 5, p. 795 - 798
  作者：Choi, Heung-Jin、Park, Yeon Sil、Yun, Seok Hun、Kim, Hong-Seok、Cho, Chan Sik、Ko, Kwangnak、Ahn, Kyo Han

  DOI：——

  日期：——