1,1'-(1,2-phenylene)bis(3-(4-tert-butylphenyl)prop-2-yn-1-ol) | 942229-67-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,1'-(1,2-phenylene)bis(3-(4-tert-butylphenyl)prop-2-yn-1-ol)
• 英文别名: 1,1′-(1,2-phenylene)bis(3-(4-(t-butyl)phenyl)prop-2-yn-1-ol)；3-(4-Tert-butylphenyl)-1-[2-[3-(4-tert-butylphenyl)-1-hydroxyprop-2-ynyl]phenyl]prop-2-yn-1-ol；3-(4-tert-butylphenyl)-1-[2-[3-(4-tert-butylphenyl)-1-hydroxyprop-2-ynyl]phenyl]prop-2-yn-1-ol
• CAS: 942229-67-6
• 化学式: C₃₂H₃₄O₂
• 分子量: 450.621
• InChiKey: OJKQSVFJSBORLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1'-(1,2-phenylene)bis(3-(4-tert-butylphenyl)prop-2-yn-1-ol) 在 吡啶 、 4-二甲氨基吡啶 、 三溴化磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 5-bromo-2-(t-butyl)-12-(4-(t-butyl)phenyl)tetracene
  参考文献：
  名称：

  PBr₃-Mediated Cyclization of 1,7-Diyn-3,6-bis(propargyl carbonate)s: Synthesis of 5-Bromotetracenes

  摘要：

  A new and straightforward method for the synthesis of 5-bromotetracenes through PBr3-mediated cyclization of 1,7-diyn-3,6-bis(propargyl carbonate)s has been developed. This method offers several advantages such as easily accessible starting materials, high efficiency, and wide functional group compatibility. In addition, chloro- and iodo-substituted tetracenes were also synthesized using appropriate halogenating reagents. The utility of the 5-bromotetracene products has been illustrated by their efficient transformations through various palladium-catalyzed cross-coupling reactions.

  DOI：

  10.1021/acs.joc.7b01519
• 作为产物：
  描述：

  4-叔-丁基苯基乙炔 、 邻苯二甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 以86%的产率得到1,1'-(1,2-phenylene)bis(3-(4-tert-butylphenyl)prop-2-yn-1-ol)
  参考文献：
  名称：

  Synthesis of Tetracene Sulfoxide and Tetracene Sulfone via a Cascade Cyclization Reaction

  摘要：

  A facile synthesis of tetracene sulfoxides and sulfones based on o-diallene annulation initiated cascade cyclization was developed. The photophysical behavior of these tetracene derivatives can be generally rationalized by the presence of electron-withdrawing sulfoxides and sulfones at the 5-position.

  DOI：

  10.1021/ol070467f

文献信息

• Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-<i>b</i>]thiophene
  作者：Laurence Burroughs、John Ritchie、Mkhethwa Ngwenya、Dilfaraz Khan、William Lewis、Simon Woodward

  DOI：10.3762/bjoc.11.31

  日期：——

  1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph, substituted phenyl, 2-thienyl) to ortho-C₆H₄(CHO)₂ undergo cascades to tetracenes on simple admixture of LiHDMS, CS₂ and MeI. Acene formation proceeds by [3,3]-sigmatropic rearrangement of xanthate anions followed by 6π electrocyclisations. The reactions are terminated by E2 or anionic Chugaev-type eliminations. Structural packing motifs and electronic properties are reported for the tetracenes.

  从ArCCLi（Ar = Ph，取代苯基，2-噻吩基）双加成到ortho-C6H4（CHO）2产生的1,4-二醇，在简单混合LiHDMS、CS2和MeI后发生级联反应生成四环芳烃。芳烃的形成通过黄硫酸酯阴离子的[3,3]-σ迁移重排，然后是6π电环化反应。反应通过E2或阴离子Chugaev型消除终止。报道了四环芳烃的结构堆积模式和电子性质。
• Gold-catalyzed cascade cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s: stereoselective synthesis of naphtho[b]cyclobutenes
  作者：Ming Chen、Jun Liu、Lu Wang、Xiaobo Zhou、Yuanhong Liu

  DOI：10.1039/c3cc44757j

  日期：——

  Gold-catalyzed cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s leads to a highly efficient and diastereoselective synthesis of functionalized naphtho[b]cyclobutenes. A cascade sequence involving gold-catalyzed double 3,3-rearrangement, 6pi-electrocyclic reaction and a decarbonylative cyclization was proposed for this reaction.

  金催化的1,7-二炔-3,6-双（炔丙基碳酸酯）s的环异构化导致官能化萘[b]环丁烯的高效和非对映选择性合成。提出了涉及金催化的双3，3-重排，6-π-电环反应和脱羰环化的级联序列。
• Understanding anionic Chugaev elimination in pericyclic tetracene formation
  作者：Laurence Burroughs、John Ritchie、Simon Woodward

  DOI：10.1016/j.tet.2016.02.025

  日期：2016.3

  in the neutral versus anionic Chugaev elimination. syn-Elimination of [HSC(=O)S]- is distinctly favoured [Eact(calcd) 11.4 kcal mol−1] versus syn elimination of neutral methylated HSC(=O)SMe [Eact(calcd) 27.5 kcal mol−1]. The smaller barrier to syn elimination of the anionic leaving group is in accord with the low temperature conditions required for this Chugaev reaction (60 °C) and suggests a general

  由二醇1,2-C 6 H 4（CHOHC CAr）2，LiHDMS，CS 2和MeI形成四烯的反应途径已通过计算方法在CBS-QB3的理论水平上进行了建模。PhCHOC的比较（= S）YCCPh（Y = S -或SME）指示用于朝向所述阴离子系统[3,3] -sigmatropic重排[E轻微动力学优点行为（计算值）19.7 21.8 VS千卡摩尔-1 ]。使用基于蒽的模型，10- SC（= O）Y} -4a，10-二氢蒽（Y = S -或SME），允许两个直接比较顺和反在中性与阴离子楚加耶夫反应-manifolds。同步-消除[HSC（= O）S] -明显受到偏爱[E行为（计算）11.4 kcal mol -1 ]与同义消除中性甲基化HSC（= O）SMe [E行为（计算）27.5 kcal mol -1 ]。较小的障碍顺式消除阴离子离去基团的是与用于本Chugaev反应（60℃）所需