o-Phenylendiessigsaeure-dichlorid | 41640-86-2

• 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: o-Phenylendiessigsaeure-dichlorid
• 英文别名: 1,2-Benzenediacetyl dichloride；2-[2-(2-chloro-2-oxoethyl)phenyl]acetyl chloride
• CAS: 41640-86-2
• 化学式: C₁₀H₈Cl₂O₂
• 分子量: 231.078
• InChiKey: YEJUQTIBEAGTGS-UHFFFAOYSA-N

物化性质

• 熔点：
  30-32 °C
• 沸点：
  322.2±35.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  o-Phenylendiessigsaeure-dichlorid 在 吡啶 、 phosphorus pentoxide 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 74.0h， 生成 (E,E)-1,2-Bis(2-acetoxy-2-cyanoethenyl)benzene
  参考文献：
  名称：

  Bis(2-acetoxyacrylonitrile) and its phenylene and alkylene bis homologs. Preparation, isomerization, and intramolecular [2 + 2] photocycloaddition

  摘要：

  The title compounds, 1,4-diacetoxy-1,4-dicyano-1,3-butadiene (3), 1,6-diacetoxy-1,6-dicyano-1,5-hexadiene (8), 1,2-bis(2-acetoxy-2-cyanovinyl)benzene (13), and 1,4-bis(2-acetoxy-2-cyanovinyl)benzene (17) were prepared by acetylation of the corresponding diacyl dicyanides. Dicyanides were prepared from diacyl chlorides by reaction with cyanotrimethylsilane or the NaI-Cu2(CN)2 reagent. Among the three geometrical isomers of the title compounds, the Z,Z diene predominated in 8 whereas E,E dienes predominated in conjugated dienes 3, 13, and 17. Conjugated E,E dienes underwent photoisomerization to E,Z and Z,Z isomers much faster than unconjugated diene 8. Prolonged irradiation on 13 yielded intramolecular [2 + 2] cycloadducts endo, exo- and exo,exo-5,6-diacetoxy-5,6-dicyano-2,3-benzobicyclo[2.1.1]hex-2-ene (22). Photochemistry in the formation of 22 is discussed.

  DOI：

  10.1021/jo00034a015
• 作为产物：
  描述：

  1,2-苯二乙腈 在 盐酸 、 氯化亚砜 作用下， 生成 o-Phenylendiessigsaeure-dichlorid
  参考文献：
  名称：

  Hadjoudis, E.; Pulima, I., Molecular Crystals and Liquid Crystals (1969-1991), 1986, vol. 137, p. 29 - 36

  摘要：

  DOI：

文献信息

• Novel bivalent securinine mimetics as topoisomerase I inhibitors
  作者：Wen Hou、Hui Lin、Zhen-Ya Wang、Martin G. Banwell、Ting Zeng、Ping-Hua Sun、Jing Lin、Wei-Min Chen

  DOI：10.1039/c6md00563b

  日期：——

  A series of novel bivalent securinine mimetics incorporating different linkers between C-15 and C-15′ were synthesized and their topoisomerase I (Topo I) inhibitory activities evaluated. It was thus revealed that mimetic R2 incorporating a rigid m-substituted benzene linker exhibits Topo I inhibitory activity three times that of parent securinine. Comprehensive structure–activity relationship analyses

  合成了一系列在C-15和C-15'之间引入不同连接子的新型二价安徽丝氨酸模拟物，并评估了它们的拓扑异构酶I（Topo I）抑制活性。因此据透露，模拟物R2结合有刚性米取代的苯接头展品拓扑异构酶I的抑制活性该父一叶的三倍。全面的结构-活性关系分析与对接研究相结合，用于合理化这些二价模拟物的有效活性。机理研究证实了对接研究的推论，即有效的二价模拟物不仅抑制了Topo I和DNA之间的复合，而且稳定了Topo I-DNA复合物本身。
• Catalytic, Asymmetric Transannular Aldolizations: Total Synthesis of (+)-Hirsutene
  作者：Carley L. Chandler、Benjamin List

  DOI：10.1021/ja8024164

  日期：2008.5.1

  We report an asymmetric, catalytic transannular aldolization that provides polycyclic products useful for natural product synthesis. We found that a proline-derivative catalyzes the transannular aldol reaction of 1,4-cyclooctanediones to the corresponding cyclic beta-hydroxy ketones in good yields and with high enantioselectivities. The utility of our reaction has been demonstrated in a total synthesis

  我们报告了一种不对称的催化跨环醛醇化反应，它提供了可用于天然产物合成的多环产物。我们发现脯氨酸衍生物以良好的产率和高对映选择性催化 1,4-环辛二酮的跨环醛醇反应生成相应的环状 β-羟基酮。我们的反应的效用已在 (+)-hirustene 的全合成中得到证明。
• Monocyclic macrocyclic compounds and complexes thereof
  申请人：Schering Corporation

  公开号：US03966766A1

  公开（公告）日：1976-06-29

  Novel monocyclic macrocyclic compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.

  具有氮桥头原子的新型单环大环化合物，在碳氢桥链中至少有两个额外的硫、氧或氮等杂原子，当与兼容的阳离子给体化合物混合时，形成稳定的含阳离子的大环化合物，这些大环化合物可以通过添加酸或季铵化剂方便地解离。这些新型大环化合物可用于与螯合剂相同的方式和目的。
• Functionalized 5‐Amino‐4‐cyanoxazoles, their Hetero‐ and Macrocyclic Derivatives: Preparation and Synthetic Applications
  作者：Danylo O. Merzhyievskyi、Oleh V. Shablykin、Olga V. Shablykina、Andriy V. Kozytskiy、Eduard B. Rusanov、Viktoriia S. Moskvina、Volodymyr S. Brovarets

  DOI：10.1002/ejoc.202100412

  日期：2021.12.21

  An approach for the synthesis of new 5-amino-4-cyanoxazoles with carboxylate group at the C-2 position, connected to the heterocycle directly or through an aliphatic linker, was developed. This process features readily available starting materials, simple operations, and good to high yields. Wide synthetic applicability of the obtained compounds was also successfully demonstrated by further modifications

  开发了一种合成新的 5-氨基-4-氰基恶唑的方法，在 C-2 位置具有羧酸盐基团，直接或通过脂肪族接头连接到杂环上。该工艺具有原料易得、操作简单、产率高到高的特点。所得化合物的广泛合成适用性也通过进一步的修饰成功证明。
• Condensation of Iminophosphoranes with Dicarbonyl Dihalides: A One-Step Synthesis of New Azepine Derivatives
  作者：Thierry Aubert、Michel Farnier、Roger Guilard

  DOI：10.1055/s-1990-26817

  日期：——

  New azepine and 3-benzazepine derivatives 3-6 have been synthesized by condensation of iminophosphoranes with adipoyl chloride and 1,2-benzenediacetyl dichloride, respectively.

  通过亚氨基正膦分别与己二酰氯和1,2-苯二乙酰二氯缩合合成了新的氮杂卓和3-苯并氮杂衍生物3-6。