methyl 4,4"-dimethyl[1,1':3',1"]terphenyl-2'-carboxylate | 155186-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4,4"-dimethyl[1,1':3',1"]terphenyl-2'-carboxylate
• 英文别名: Methyl 2,6-bis(4-methylphenyl)benzoate
• CAS: 155186-07-5
• 化学式: C₂₂H₂₀O₂
• 分子量: 316.4
• InChiKey: LISCIWDISWGUFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4,4"-dimethyl[1,1':3',1"]terphenyl-2'-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 反应 4.0h， 以18%的产率得到methyl 4-formyl-4"-methyl[1,1':3',1"]terphenyl-2'-carboxylate
  参考文献：
  名称：

  大环和“ C-钳位”二羧酸酯化合物的制备

  摘要：

  将双-1,3-（氨基甲基）-4,6-二异丙基苯与1,1'：3'，1''-三联苯-2'-羧酸的4,4''-二甲醛进行还原胺化，得到钠盐一种新型的大环二羧酸盐化合物，分离产率为71％。通过一步过滤进行纯化。合成和两个新的“C形夹”的化合物，其还包含两个表征米三联苯羧酸盐但表现出的柔韧性更大的程度，也有所说明。这些化合物作为潜在的配体或用于客体-客体化学是令人感兴趣的。

  DOI：

  10.1016/s0040-4020(03)00256-4
• 作为产物：
  描述：

  2,6-双(4-甲基苯基)苯甲酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl 4,4"-dimethyl[1,1':3',1"]terphenyl-2'-carboxylate
  参考文献：
  名称：

  2′-Substituted meta-terphenyls as building blocks for cyclophanes with intra-annular functionality

  摘要：

  2'-Substituted m-terphenyls containing chloromethyl and/or thiomethyl groups at the 4,4'' or 3,3'' positions are used as building blocks for cyclophanes with intra-annular functionality. Syntheses are short and yields are good. The methodology, capable of wide structural variation, has been adapted to bi- and tricyclic cyclophanes.

  DOI：

  10.1016/0040-4020(94)01016-s

文献信息

• Synthesis, complexation studies and biological applications of some novel stilbenophanes, indolophanes and bisindolostilbenophanes via McMurry coupling
  作者：Perumal Rajakumar、Merikapudi Gayatri Swaroop、S. Jayavelu、K. Murugesan

  DOI：10.1016/j.tet.2006.09.078

  日期：2006.12

  Various types of stilbenophanes, indolophanes and bisindolostilbenophanes were synthesized by intra-, inter- and tandem intra-, intermolecular McMurry coupling. Some of the indolophanes and bisindolostilbenophanes exhibited significant activity against the growth of various bacteria. Complexation of some of the cyclophanes with TCNQ has also been studied. (c) 2006 Elsevier Ltd. All rights reserved.
• The use of McMurry coupling for the synthesis of indolophanes and cis-stilbenophanes
  作者：Perumal Rajakumar、Merikapudi Gayatri Swaroop

  DOI：10.1016/j.tetlet.2004.06.020

  日期：2004.8

  Treatment of 2 equiv of indole-3-aidehyde with o, m, p-xylyl, 2,5-dimethoxy-p-xylyl dibromides and 4,4'-bis(bromomethyl)-1,1'-biphenyl gave the bisalkylated products, which underwent McMurry coupling with low valent titanium to give indolophanes. Various cis-stilbenophanes with m-terphenyl building blocks were also synthesized by application of the McMurry coupling technique. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of functionalised cyclophanes with cage structure; via an unusual termolecular collision
  作者：Perumal Rajakumar、Arunachalam Kannan

  DOI：10.1016/s0040-4039(00)61420-x

  日期：1993.12

  Coupling of the tetrathiol 11 with two equivalents of the dibromide 6,7 and 8 under high dilution technique in the presence of KOH in benzene - ethanol afforded the cyclophanes 1a, 1c & 1b respectively. Similarly cyclophane 1d was obtained from the tetrathiol 11 and tetrabromide 9.
• Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure
  作者：Arunachalam Kannan、Perumal Rajakumar、V. Kabaleeswaran、S. S. Rajan

  DOI：10.1021/jo950957y

  日期：1996.1.1

  Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-alpha,alpha'-dithiol (9), p-xylene-alpha,alpha'-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide Bb or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol as with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by H-1 NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex.
• 2′-Substituted meta-terphenyls as building blocks for cyclophanes with intra-annular functionality
  作者：Harold Hart、Perumal Rajakumar

  DOI：10.1016/0040-4020(94)01016-s

  日期：1995.1

  2'-Substituted m-terphenyls containing chloromethyl and/or thiomethyl groups at the 4,4'' or 3,3'' positions are used as building blocks for cyclophanes with intra-annular functionality. Syntheses are short and yields are good. The methodology, capable of wide structural variation, has been adapted to bi- and tricyclic cyclophanes.