(3',5'-dimethoxyphenyl)phenylethane-1,2-dione | 188924-61-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3',5'-dimethoxyphenyl)phenylethane-1,2-dione
• 英文别名: 1-(3,5-Dimethoxyphenyl)-2-phenylethan-1,2-dione；1-(3,5-dimethoxyphenyl)-2-phenylethane-1,2-dione
• CAS: 188924-61-0
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: WHBBHBDUACEGRV-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±35.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3',5'-dimethoxyphenyl)phenylethane-1,2-dione 在 吡啶 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 生成 [1-(3,5-dimethoxyphenyl)-2-oxo-2-phenylethyl] [(2R,3S,5R)-3-hydroxy-5-[6-oxo-2-[(2-phenoxyacetyl)amino]-1H-purin-9-yl]oxolan-2-yl]methyl carbonate
  参考文献：
  名称：

  Proofing of Photolithographic DNA Synthesis with 3‘,5‘-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites

  摘要：

  We have evaluated in a microchip format the photochemical solid-phase phosphoramidite DNA synthesis method we previously developed. A set of nucleoside building blocks with "easy-off" base protecting groups was prepared bearing photolabile 5'-O-dimethoxybenzoincarbonate (DMBOC) groups. Photolysis rates and cycle yields for these DMBOC-protected nucleotides covalently attached to planar, derivatized glass surfaces were determined by fluorescence imaging-based methods earlier developed by McGall et al. and described in detail elsewhere. Data were obtained for both 280/310 and 365/400 nm irradiation in a range of solvents. Deprotection of the DMBOC occurs fastest in a nonpolar medium or without solvent. The coupling efficiency of these amidites in the synthesis of homopolymers was determined to be in the range 80-97%, with purines generally showing lower efficiency than pyrimidines. These DMBOC-protected monomers were used to prepare a 4 x 4 array of 16 decanucleotides of the sequence 5'-AAXTAXCTAC-chip, where X = A, C, G, or T. The array was hybridized with a target deoxyeicosanucleotide of the sequence fluorescein-5'-CTGAACG-GTAGCATCTTGAC. Surface fluorescence imaging demonstrated sequence-specific hybridization to this probe.

  DOI：

  10.1021/jo970872s
• 作为产物：
  描述：

  3,5-dimethoxybenzoin 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以48%的产率得到(3',5'-dimethoxyphenyl)phenylethane-1,2-dione
  参考文献：
  名称：

  光不稳定性苯偶姻氨基甲酰基衍生物的合成及性能

  摘要：

  光不稳定的安息香，特别是3'，5'-二甲氧基安息香的氨基甲酰基衍生物可以通过安息香的混合对硝基苯基碳酸酯容易地制备。该方法最适合于仲胺，因为许多伯胺以不同的比例作为环状羟基恶唑烷酮互变异构体存在。在碱性溶液（0.2 M NaOH）中，不对称安息香的氨基甲酸酯很容易达到平衡。3'，5'-二甲氧基苯偶姻氨基甲酸酯的快速光解会在快速杂解过程中生成氨基甲酸酯阴离子，胺的释放受脱羧速率的控制。

  DOI：

  10.1016/s0040-4020(97)00009-4

文献信息

• 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。
• Wavelength-Controlled Orthogonal Photolysis of Protecting Groups
  作者：Aurélien Blanc、Christian G. Bochet

  DOI：10.1021/jo025837m

  日期：2002.8.1

  The selective control of a chemical process by the use of an electromagnetic wave has been a challenging goal for several decades. In this article, we describe for the first time the use of a monochromatic light beam to differentiate two different reactive centers. A direct application of this concept is found in the chemistry of protecting groups. Two different photolabile protecting groups were tuned to be responsive to a specific wavelength (e.g., 254 or 420 nm). Using derivatives of the 2-nitroveratryl fragment (such as 10, sensitive at 420 nm) and 3',5'-dimethoxybenzoin fragment (such as 4, sensitive at 254 nm), it was shown that energy transfer phenomena did not erode the selectivity. Both the inter- and the intramolecular cases were studied and showed selectivities within the synthetically useful range. Hence, we could replace the traditional chemical orthogonality by a chromatic orthogonality.
• Synthesis and properties of carbamoyl derivatives of photolabile benzoins
  作者：George Papageorgiou、John E.T. Corrie

  DOI：10.1016/s0040-4020(97)00009-4

  日期：1997.3

  Carbamoyl derivatives of photolabile benzoins, particularly of 3′,5′-dimethoxybenzoin, are readily prepared via the mixed p-nitrophenyl carbonate of the benzoin. The method is most suitable for secondary amines, since many primary amines exist in varying proportions as the cyclic hydroxyoxazolidinone tautomer. In alkaline solution (0.2 M NaOH) the carbamates of unsymmetrical benzoins are readily equilibrated

  光不稳定的安息香，特别是3'，5'-二甲氧基安息香的氨基甲酰基衍生物可以通过安息香的混合对硝基苯基碳酸酯容易地制备。该方法最适合于仲胺，因为许多伯胺以不同的比例作为环状羟基恶唑烷酮互变异构体存在。在碱性溶液（0.2 M NaOH）中，不对称安息香的氨基甲酸酯很容易达到平衡。3'，5'-二甲氧基苯偶姻氨基甲酸酯的快速光解会在快速杂解过程中生成氨基甲酸酯阴离子，胺的释放受脱羧速率的控制。
• Proofing of Photolithographic DNA Synthesis with 3‘,5‘-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites
  作者：Michael C. Pirrung、Lara Fallon、Glenn McGall

  DOI：10.1021/jo970872s

  日期：1998.1.1

  We have evaluated in a microchip format the photochemical solid-phase phosphoramidite DNA synthesis method we previously developed. A set of nucleoside building blocks with "easy-off" base protecting groups was prepared bearing photolabile 5'-O-dimethoxybenzoincarbonate (DMBOC) groups. Photolysis rates and cycle yields for these DMBOC-protected nucleotides covalently attached to planar, derivatized glass surfaces were determined by fluorescence imaging-based methods earlier developed by McGall et al. and described in detail elsewhere. Data were obtained for both 280/310 and 365/400 nm irradiation in a range of solvents. Deprotection of the DMBOC occurs fastest in a nonpolar medium or without solvent. The coupling efficiency of these amidites in the synthesis of homopolymers was determined to be in the range 80-97%, with purines generally showing lower efficiency than pyrimidines. These DMBOC-protected monomers were used to prepare a 4 x 4 array of 16 decanucleotides of the sequence 5'-AAXTAXCTAC-chip, where X = A, C, G, or T. The array was hybridized with a target deoxyeicosanucleotide of the sequence fluorescein-5'-CTGAACG-GTAGCATCTTGAC. Surface fluorescence imaging demonstrated sequence-specific hybridization to this probe.