2-[4,7-Bis(bromomethyl)-1,3-dioxoisoindol-2-yl]acetic acid | 753006-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[4,7-Bis(bromomethyl)-1,3-dioxoisoindol-2-yl]acetic acid
• 英文别名: 2-[4,7-bis(bromomethyl)-1,3-dioxoisoindol-2-yl]acetic acid
• CAS: 753006-59-6
• 化学式: C₁₂H₉Br₂NO₄
• 分子量: 391.016
• InChiKey: YSZQPRPWWWGARD-UHFFFAOYSA-N

物化性质

• 熔点：
  228.0-230.5 °C
• 沸点：
  571.5±50.0 °C(Predicted)
• 密度：
  2.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4,7-Bis(bromomethyl)-1,3-dioxoisoindol-2-yl]acetic acid 在 4-二甲氨基吡啶 、 ammonium hexafluorophosphate 、 4-甲基苯磺酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Stereochemistry of Molecular Figures-of-Eight

  摘要：

  AbstractA trans isomer of a figure‐of‐eight (Fo8) compound was prepared from an electron‐withdrawing cyclobis(paraquat‐p‐phenylene) derivative carrying trans‐disposed azide functions between its two phenylene rings. Copper(I)‐catalyzed azide–alkyne cycloadditions with a bispropargyl derivative of a polyether chain, interrupted in its midriff by an electron‐donating 1,5‐dioxynaphthalene unit acting as the template to organize the reactants prior to the onset of two click reactions, afforded the Fo8 compound with Ci symmetry. Exactly the same chemistry is performed on the cis‐bisazide of the tetracationic cyclophane to give a Fo8 compound with C2 symmetry. Both of these Fo8 compounds exist as major and very minor conformational isomers in solution. The major conformation in the trans series, which has been characterized by X‐ray crystallography, adopts a geometry which maximizes its CH⋅⋅⋅O interactions, while maintaining its π⋅⋅⋅π stacking and CH⋅⋅⋅π interactions. Ab initio calculations at the M06L level support the conformational assignments to the major and minor isomers in the trans series. Dynamic 1H NMR spectroscopy, supported by 2D 1H NMR experiments, indicates that the major and minor isomers in both the cis and trans series equilibrate in solution on the 1H NMR timescale rapidly above and slowly below room temperature.

  DOI：

  10.1002/chem.201202070
• 作为产物：
  描述：

  (4,7-Dimethyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid tert-butyl ester 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 硝酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-[4,7-Bis(bromomethyl)-1,3-dioxoisoindol-2-yl]acetic acid
  参考文献：
  名称：

  热和电化学可控的自复合分子开关

  摘要：

  当臂组分（pi 供体）与预先形成的大环（pi 受体）共价连接时，会获得自复合分子系统。由此产生的自复合化合物不仅在其拓扑结构方面具有吸引力，而且还具有进行可逆运动的潜力，即臂可以响应温度或施加的电压而被驱动出或进入连接的大环的空腔. 这些结构上敏感的变化使它们成为潜在的热传感器或电子开关。

  DOI：

  10.1021/ja048164t

文献信息

• A bistable pretzelane
  作者：Yan-Li Zhao、Ali Trabolsi、J. Fraser Stoddart

  DOI：10.1039/b910510g

  日期：——

  A switchable donor–acceptor pretzelane composed of a crown ether containing tetrathiafulvalene and 1,5-dihydroxynaphthalene recognition units and a covalently tethered cyclobis(paraquat-p-phenylene) ring exhibits unidirectional motion on both oxidation (forwards) and reduction (backwards).

  由包含四硫富瓦烯和1,5-二羟基萘识别单元以及共价连接的苯并双(对四甲基二吡啶)环的冠醚构成的可切换供体-受体扭结型分子，在氧化（向前）和还原（向后）过程中均表现出单向运动。
• Template-Directed Syntheses of Configurable and Reconfigurable Molecular Switches
  作者：J. Fraser Stoddart、Yi Liu、Sourav Saha、Scott A. Vignon、Amar H. Flood

  DOI：10.1055/s-2005-918468

  日期：——

  self-complexing compounds based on donor-acceptor interactions, one comprised of a π-electron-deficient cyclo-bis(paraquat-p-phenylene) (CBPQT 4 + ) ring attached to a side-arm component containing π-electron-rich tetrathiafulvalene (TTF) and 1,5-dioxynaphthalene (DNP) units, and the other comprised of a CBPQT 4 + ring carrying two side-arms, one containing a TTF unit and the other a DNP unit have been synthesized

  两种基于供体-受体相互作用的自络合化合物，一种由 π 电子缺陷型环双(百草枯-对苯撑) (CBPQT 4 + ) 环连接到含有 π 电子富集的侧臂组件上已经合成了四硫富瓦烯 (TTF) 和 1,5-二氧萘 (DNP) 单元，另一个由带有两个侧臂的 CBPQT 4 + 环组成，一个包含一个 TTF 单元，另一个包含一个 DNP 单元。'H NMR 光谱和 UV/Vis 光谱电化学表明，虽然后一种化合物表现为可重构的氧化还原活性分子开关，但仅涉及含有 TTF 单元的侧臂，与 CBPQT 4 + 环具有自络合作用（包含 DNP 单元的侧臂本质上是一个“观众”），
• Versatile Self-Complexing Compounds Based on Covalently Linked Donor-Acceptor Cyclophanes
  作者：Yi Liu、Amar H. Flood、Ross M. Moskowitz、J. Fraser Stoddart

  DOI：10.1002/chem.200400614

  日期：2005.1

  of the arm. In the case of compounds carrying a DNP ring system in their side arm, two diastereoisomeric, self-complexing conformations are observed below 272 K in hexadeuterioacetone. By contrast, control over the TTF-containing arm's movement is more or less ineffective through the thermally sensitive equilibrium although it can be realized by chemical and electrochemical ways as a result of TTF's

  一系列共价连接的供体-受体化合物，包含1）对苯二酚（HQ）单元，2）1,5-二氧萘（DNP）环系统或3）噻吩富勒烯（TTF）单元作为pi-供体，和4）制备了作为pi接受的四阳离子环烷的环双（百草枯-对亚苯基）（CBPQT（4+）），并显示其可作为简单的分子机器操作。可以通过稳定非共价键相互作用以分子内方式将pi供体臂包括在环烷内。当pi供体臂包含HQ或DNP部分时，表明自复合/解复合平衡的程度与温度高度相关。已通过使用可变温度（1）H NMR光谱图阐明了与平衡相关的热力学参数。负DeltaH度和DeltaS度值说明了以下事实：“未复合”构象成为主要物质，因为与复合过程相关的熵增益克服了由于供体-受体相互作用破坏而产生的焓损失。可以通过在臂的末端安装庞大的取代基来阻止臂相对于连接的环戊烯的进出运动。在化合物的侧臂带有DNP环系统的情况下，在六氘代丙酮中，在272 K以下观察到两个非对映异构体
• Conformational diastereoisomerism in a chiral pretzelane
  作者：Yi Liu、Scott A. Vignon、Xiyun Zhang、K. N. Houk、J. Fraser Stoddart

  DOI：10.1039/b507679j

  日期：——

  The introduction of a stereogenic center by a stereospecific synthesis into an optically active, donor-acceptor pretzelane, that exhibits helicity as well as fixed chirality, leads to a marked preference for one conformational diastereoisomer over the other in both acetone and dimethylsulfoxide that can be understood from computational models.

  通过立体特异性合成将立体异构中心引入旋光性和固定手性的旋光性供体-受体椒盐卷饼中，导致丙酮和二甲亚砜中一种构象非对映异构体明显优于另一种构象非对映异构体从计算模型。
• Dynamic Chirality in Donor−Acceptor Pretzelanes
  作者：Y. Liu、S. A. Vignon、X. Zhang、P. A. Bonvallet、S. I. Khan、K. N. Houk、J. F. Stoddart

  DOI：10.1021/jo051430g

  日期：2005.11.1

  A series of donor-acceptor pretzelanes has been synthesized, using self-assembly and template-directed protocols, and the dynamic processes that these pretzelanes undergo have been investigated in solution. These compounds exist as libraries of diastereoisomers as a result of their multiple stereoelements, which are dynamically interconverted by several different, in some cases competing, processes. Altering the structure of the pretzelanes changes the rates and mechanisms by which these diastereoisomers equilibrate. Additionally, inserting an element of fixed chirality allows the equilibrium to be biased, while maintaining the barrier to the equilibration processes. These results bode well for the future construction of molecular devices based on switchable diastereoisomerism involving metastable states.