1,2-双-苯并[1,3]1,3-二氧杂环戊烯-5-基-乙烷-1,2-二酮 | 4720-66-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,2-双-苯并[1,3]1,3-二氧杂环戊烯-5-基-乙烷-1,2-二酮
• 英文名称: Piperil
• 英文别名: 1,2-bis-benzo(1,3)dioxol-5-yl-ethane-1,2-dione；1,2-bis(benzo[d][1,3]dioxol-5-yl)ethane-1,2-dione；1,2-bis(1,3-benzodioxol-5-yl)ethane-1,2-dione；1,2-bis(1,3-benzodioxol-5-yl)-1,2-ethanedione；3,4,3',4'-bis(methylenedioxy)-benzil；bis-benzo[1,3]dioxol-5-yl-ethanedione；Bis-benzo[1,3]dioxol-5-yl-aethandion；bis(3,4-methylenedioxy)benzil
• CAS: 4720-66-5
• 化学式: C₁₆H₁₀O₆
• mdl: MFCD01250244
• 分子量: 298.252
• InChiKey: IUBVHENRQMZUQG-UHFFFAOYSA-N

物化性质

• 熔点：
  171.5 °C
• 沸点：
  516.6±50.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1,2-双-苯并[1,3]1,3-二氧杂环戊烯-5-基-乙烷-1,2-二酮 在 乙醇 、 sodium 、 sodium amide 、 甲苯 作用下， 生成 bis(benzo[d][1,3]dioxol-5-yl)methane
  参考文献：
  名称：

  Garofano; Oliverio, Annali di Chimica, 1957, vol. 47, p. 896,904

  摘要：

  DOI：
• 作为产物：
  描述：

  2-benzoyloxy-2-(3',4'-methylenedioxyphenyl)-acetonitrile 在 苄基三乙基氯化铵 sodium hydroxide 作用下， 以 水 、 乙腈 、 苯 为溶剂， 生成 1,2-双-苯并[1,3]1,3-二氧杂环戊烯-5-基-乙烷-1,2-二酮
  参考文献：
  名称：

  氰醇作为安息香缩合中的底物。：区域控制的混合安息香缩合

  摘要：

  芳族醛的邻苯甲酰氰醇已被用作安息香缩合反应的底物之一。它们在相转移条件下用芳香醛处理，得到苯偶姻苯甲酸酯。通过这种方法，在传统条件下无法缩合的醛可以转化为苯偶姻。通过相关醛的反应性的Umpolung，可以制备两种异构的不对称安息香，包括热力学上较不稳定的安息香。

  DOI：

  10.1016/s0040-4020(01)96667-0

文献信息

• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR THE TREATMENT OF AMYLOID DISEASES AND SYNUCLEINOPATHIES SUCH AS ALZHEIMER'S DISEASE, TYPE 2 DIABETES, AND PARKINSON'S DISEASE<br/>[FR] COMPOSES, COMPOSITIONS ET PROCEDES DE TRAITEMENT DE MALADIES AMYLOIDES ET DE SYNUCLEINOPATHIES, NOTAMMENT DE LA MALADIE D'ALZHEIMER, DU DIABETE DE TYPE 2 ET DE LA MALADIE DE PARKINSON
  申请人：PROTEOTECH INC

  公开号：WO2003101927A1

  公开（公告）日：2003-12-11

  Bis- and tris-dihydroxyaryl compounds and their methylenedioxy analogs and pharmaceutically acceptable esters, their synthesis, pharmaceutical compositions containing them, and their use in the treatment of amyloid diseases, especially Aß amyloidosis, such as observed in Alzheimer's disease, IAPP amyloidosis, such as observed in type 2 diabetes, and synucleinophathies, such as observed in Parkinson's disease, and the manufacture of medicaments for such treatment.

  双-和三-二羟基芳基化合物及其亚甲二氧基类似物和药用可接受酯，它们的合成，含有它们的药物组合物，以及它们在治疗淀粉样疾病，特别是Aß淀粉样病变，如阿尔茨海默病中观察到的，IAPP淀粉样病变，如2型糖尿病中观察到的，以及α-突触核病，如帕金森病中观察到的，以及用于制造用于此类治疗的药物。
• Sol-Gel Synthesis of Ceria-Zirconia-Based High-Entropy Oxides as High-Promotion Catalysts for the Synthesis of 1,2-Diketones from Aldehyde
  作者：Dalibor Tatar、Jelena Kojčinović、Berislav Marković、Aleksandar Széchenyi、Aleksandar Miletić、Sándor Balázs Nagy、Szilveszter Ziegenheim、Imre Szenti、Andras Sapi、Ákos Kukovecz、Kristijan Dinjar、Yushu Tang、David Stenzel、Gábor Varga、Igor Djerdj

  DOI：10.3390/molecules26206115

  日期：——

  Efficient Lewis-acid-catalyzed direct conversion of aldehydes to 1,2-diketones in the liquid phase was enabled by using newly designed and developed ceria–zirconia-based high-entropy oxides (HEOs) as the actual catalysts. The synergistic effect of various cations incorporated in the same oxide structure (framework) was partially responsible for the efficiency of multicationic materials compared to

  通过使用新设计和开发的基于氧化铈-氧化锆的高熵氧化物 (HEO) 作为实际催化剂，可以在液相中高效地将路易斯酸催化的醛直接转化为 1,2-二酮。与相应的单阳离子氧化物形式相比，在同一氧化物结构（框架）中掺入的各种阳离子的协同效应是多阳离子材料效率的部分原因。此外，观察到路易斯酸度与 HEO 的催化活性之间存在明确的线性关系。由于所开发的策略，可以在温和的反应条件下实现醛的完全二酮选择性、可回收、通用的多相催化转化。
• Bis(2,2'-bipyridyl)copper(II) permanganate (BBCP): A mild and versatile oxidant in organic synthesis
  作者：H. Firouzabadi、A.R. Sardarian、M. Naderi、B. Vessal

  DOI：10.1016/s0040-4020(01)91340-7

  日期：1984.1

  The preparation of bis(2,2'-bipyridyl)copper(II) permanganate (BBCP) is described. The reagent converts alcohols to the corresponding carbonyl compounds, α-hydroxy ketones to diketones, hydroquinone to p-benzoquinone, and compounds with benzylic double bonds to benzaldehyde in high yield. Benzophenone oxime, acetophenone oxime and various benzaldoximes are converted to the corresponding carbonyl compounds

  描述了高锰酸双（2,2'-联吡啶基）铜（II）（BBCP）的制备。该试剂以高收率将醇转化为相应的羰基化合物，将α-羟基酮转化为二酮，将氢醌转化为对苯醌，将具有苄基双键的化合物转化为苯甲醛。通常在温和的条件下，通常以高收率将苯甲酮肟，苯乙酮肟和各种苯甲醛肟转化为相应的羰基化合物，将芳族胺转化为偶氮化合物，将苄胺转化为苯甲醛。
• Photogeneration of amines from α-keto carbamates: design and preparation of photoactive compounds
  作者：James F. Cameron、C. Grant Willson、Jean M. J. Fréchet

  DOI：10.1039/a602018f

  日期：——

  The design and synthesis of substituted desyl (2-oxo-1,2-diphenylethyl) groups has been investigated to create new photolabile protecting groups. The photoreactivity of these chromophores stems from the diverse photochemistry of the desyl group. Several chromophore designs have been explored in which the substitution pattern of the parent desyl chromophore was varied systematically. The required benzoin chromophores are prepared by a variety of synthetic routes, depending on the structure of the benzoin chromophore desired. Symmetrical benzoins are readily available via the benzoin condensation. Unsymmetrical benzoins including 2,2-disubstituted α-hydroxy ketones are generally prepared via trimethylsilyl (TMS) masked cyanohydrins. On reaction with a Grignard reagent, the TMS masked cyanohydrin functions as an α-hydroxycarbonyl equivalent to form α-hydroxy ketones. Alternatively, lithiation of a TMS masked cyanohydrin generates a benzoyl anion equivalent which reacts with aldehydes and ketones to generate substituted benzoins. These desyl chromophores have significant potential as new photolabile protecting moieties for a variety of functional groups and are used to mask primary and secondary amines as photosensitive α-keto carbamates. The substituted benzoin carbamates are readily prepared from the appropriate benzoin by reaction with isocyanates or by activation as a mixed carbonate followed by reaction with the free amine. These α-keto carbamates are interesting for two main reasons. First, the facile synthesis of these materials indicates the ease of introduction of the desyl based photolabile group. Second, these α-keto carbamates may be used for rapid evaluation of novel photoactive desyl based chromophores.

  对取代的德亚尔（2-氧-1,2-二苯乙基）基团的设计和合成进行了研究，以创建新的光敏保护基团。这些颜料的光反应性源于德亚尔基团的多样光化学。已经探索了几种颜料设计，其中母体德亚尔颜料的取代模式被系统地变化。所需的苯基醇颜料通过多种合成途径制备，这取决于所需苯基醇颜料的结构。对称的苯基醇可以通过苯基醇缩合法轻松获得。包括2,2-二取代的α-羟基酮在内的不对称苯基醇通常通过三甲基硅基（TMS）掩蔽氰醇生成。与格氏试剂反应时，TMS掩蔽氰醇作为α-羟基羰基等价物，形成α-羟基酮。或者，TMS掩蔽氰醇的锂化生成苯甲酰阴离子等价物，与醛和酮反应生成取代苯基醇。这些德亚尔颜料作为新型光敏保护基团在多种功能基团中具有重要潜力，被用于掩蔽一级和二级胺，作为光敏α-酮氨基甲酸酯。取代的苯基醇氨基甲酸酯可以通过与异氰酸酯反应，或通过作为混合碳酸盐活化后与游离胺反应，从适当的苯基醇中容易制备。这些α-酮氨基甲酸酯在两个主要方面颇具趣味。首先，这些材料的简单合成表明引入德亚尔基光敏基团的容易性。其次，这些α-酮氨基甲酸酯可用于快速评估新型光活性德亚尔基颜料。
• Cerium(IV) ammonium nitrate-charcoal system. An effective catalyst for the air oxidation of benzyl alcohols and acyloins
  作者：Yasuo Hatanaka、Tsuneo Imamoto、Masataka Yokoyama

  DOI：10.1016/s0040-4039(00)81936-x

  日期：1983.1

  Cerium(IV) ammonium nitrate (CAN) adsorbed on activated charcoal has been found to be an effective catalyst for the air oxidation of benzyl alcohols and acyloins to the corresponding carbonyl compounds.

  已经发现，吸附在活性炭上的硝酸铈（IV）铵（CAN）是一种有效的催化剂，用于将苄醇和酰氯空气氧化为相应的羰基化合物。