酞酸酐-d4 | 75935-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 酞酸酐-d4
• 中文别名: 苯酐-D4；邻苯二甲酸酐-D4
• 英文名称: phthalic anhydride-d4
• 英文别名: Phthalic-D4 anhydride；4,5,6,7-tetradeuterio-2-benzofuran-1,3-dione
• CAS: 75935-32-9
• 化学式: C₈H₄O₃
• 分子量: 152.086
• InChiKey: LGRFSURHDFAFJT-RHQRLBAQSA-N

物化性质

• 熔点：
  131-134 °C (lit.)
• 沸点：
  284 °C (lit.)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 稳定性/保质期：
  1. 摩尔折射率：35.68 2. 摩尔体积（m³/mol）：102.5 3. 等张比容（90.2K）：283.1 4. 表面张力（dyne/cm）：58.0 5. 极化率：14.14 6. 介电常数：未确定

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22
• WGK Germany：
  1
• 危险品运输编号：
  UN 2214 8/PG 3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  酞酸-3,4,5,6-d4	phthalic-d4 acid	87976-26-9	C8H6O4	170.101

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  邻苯二甲酸异丁酯-D4	mono-n-butyl phthalate-d4	478954-81-3	C12H14O4	226.209
  ——	mono-(2-ethylhexyl) phthalate-d4	1276197-22-8	C16H22O4	282.317
  单(2-乙基-5-羟基己基)邻苯二甲酸酯-d4	mono(2-ethyl-5-hydroxyhexyl) (3,4,5,6-2H4)-phthalate	679789-43-6	C16H22O5	298.316
  ——	phthalic acid (3,4,5,6-2H4) mono(5-carboxy-2-ethylpentyl)ester	——	C16H20O6	312.299
  外消旋单(2-乙基-5-氧代己基)邻苯二甲酸酯-d4	mono(2-ethyl-5-oxohexyl) (3,4,5,6-2H4)-phthalate	679789-44-7	C16H20O5	296.3
  ——	(2-ethyl-5-oxo-hexyl) methylthiomethyl (3,4,5,6-2H4)-phthalate	——	C18H24O5S	356.42

反应信息

• 作为反应物：
  描述：

  酞酸酐-d4 以99%的产率得到benzyne-d4
  参考文献：
  名称：

  Infrared spectrum of o-benzyne: experiment and theory

  摘要：

  The complete set of vibrational frequencies and absolute infrared intensities has been determined for omicron-benzyne and two of its isotopomers: C6D4 and 1,2-(C2C4H4)-C-13. In addition, for the majority of the transitions symmetries were assigned from infrared linear dichroism of the matrix-isolated samples, photooriented with polarized light during several photochemical transformations. Thermal relaxation of the high static pressure created by the initial photofragmentation causes dramatic changes of the fine site structure of each band of omicron-benzyne and results in a single-site infrared absorption spectra. A high-resolution, single-site vibrational spectrum was also obtained independently from laser hole-burning experiments. Band-shape analysis in different inert gas matrices (Ne, Ar, Xe, N2, and CO) greatly facilitates the correlation of isotopomer bands with those of unlabeled omicron-benzyne. The triple bond stretching vibration appears at 1846 cm-1 in a Ne matrix, with an experimental absolute intensity of 2.0 +/- 0.4 km/mol in the unlabeled omicron-benzyne and is polarized along the symmetry axis. It is red-shifted by 2 cm-1 in the perdeutero-omicron-benzyne and by 53 cm-1 in the doubly C-13-labeled compound, in very good agreement with our theoretical prediction (MP2/6-31G**) and previous gas-phase data for omicron-benzyne.

  DOI：

  10.1021/ja00027a007
• 作为产物：
  描述：

  酞酸-3,4,5,6-d4 在 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到酞酸酐-d4
  参考文献：
  名称：

  ONSH：通过研究反应机理优化氧化性烷基化反应

  摘要：

  自从引入AgPy 2 MnO 4作为氧化剂以来，通过氢的亲核取代，缺电子的（杂）芳族化合物的氧化烷基胺化已取得了重大进展。这种氧化剂通常能提供良好的转化率和产率，而使用KMnO 4有时效果却很好。为了使其合理化，已经研究了氧化烷基胺化的反应机理。选择3-硝基吡啶（1），1,3-二硝基苯（2）和喹唑啉（3）作为模型底物，n-丁胺和吡咯烷作为模型烷基胺。确定了这些底物/烷基胺组合的机理的限速步骤。与使用1 H NMR光谱的σ热力学性质Η -adduct形成推导出并在加合物形成的添加剂的效果进行了研究。这些研究得出的基本见解导致了对廉价添加剂（氯化四丁基铵）的鉴定，该添加剂与标准廉价氧化剂KMnO 4结合通常可提供优异的收率，类似于先前使用更昂贵的AgPy 2 MnO 4获得的收率。

  DOI：

  10.1021/jo100858n

文献信息

• Convenient and High-Yielding Preparations of Mono(5-carboxy-2-ethylpentyl) Phthalate and its Ring-Deuterated Isomer – The “Third” Major Metabolite of Bis(2-ethylhexyl) Phthalate
  作者：Hans-Detlev Gilsing、Jürgen Angerer、Dietrich Prescher

  DOI：10.1007/s00706-004-0267-6

  日期：2005.5

  The synthesis of an oxidative major metabolite of bis(2-ethylhexyl) phthalate is described. The target molecule and its ring-deuterated isomer were obtained via acylation of the appropriate ω-hydroxy benzyl ester or the corresponding carboxylate with phthalic anhydride or phthalic anhydride-d4. All transformation steps proceed with high yields.

  描述了邻苯二甲酸二（2-乙基己基）酯的氧化性主要代谢产物的合成。通过将适当的ω-羟基苄基酯或相应的羧酸酯与邻苯二甲酸酐或邻苯二甲酸酐-d 4酰化，获得目标分子及其环氘代异构体。所有转化步骤均以高收率进行。
• Decomposition of Gaseous Phthalic Anhydride from a Vibrationally Hot Molecule Formed by ArF Laser Irradiation
  作者：Tomoyuki Yatsuhashi、Nobuaki Nakashima

  DOI：10.1021/jp992469q

  日期：2000.1.1

  The photodecomposition of gaseous phthalic anhydride (PA) has been studied by ArF laser photolysis. The transient absorption profiles were strongly dependent on the concentration of the ground-state PA, the foreign gas pressure, and the laser fluence. Both biphenylene and triphenylene were detected as the final products. These results clearly indicated that benzyne (1,3-cyclohexadien-5-yne) was formed

  ArF激光光解研究了气态邻苯二甲酸酐（PA）的光解。瞬态吸收曲线强烈依赖于基态 PA 的浓度、外来气体压力和激光能量密度。亚联苯和三亚苯都被检测为最终产物。这些结果清楚地表明在光解过程中形成了苯炔（1,3-cyclohexadien-5-yne）。外来气体对联苯形成的猝灭清楚地表明，联苯源自高度振动激发（热）的中间体。发现热的 PA 和苯是 PA 分解反应的中间体。
• Isotope Edited Internal Standard Method for Quantitative Surface-Enhanced Raman Spectroscopy
  作者：Dongmao Zhang、Yong Xie、Shirshendu K. Deb、V. Jo Davison、Dor Ben-Amotz

  DOI：10.1021/ac050338h

  日期：2005.6.1

  A new isotope edited internal standard (IEIS) method for quantitative surface-enhanced Raman spectroscopy (SERS) is demonstrated using rhodamine 6G (R6G-d0) and rhodamine 6G (R6G-d4) edited with deuterium. The reproducibility and accuracy of the IEIS method is investigated both under optical resonance (SERRS) and nonresonance (SERS) conditions. A batch-to-batch concentration measurement reproducibility of better than 3% is demonstrated over a concentration range of 200 pM−2 μM with up to a factor of 3 difference between the concentration of the analyte and its IEIS. The superior performance of the IEIS method is further illustrated by comparing results obtained using absolute SERS/SERRS intensity calibration (with no internal standard) or using adenine (rather than R6G-d4) as an internal standard for R6G concentration quantization. Potential biomedical gene expression and comparative proteomic applications of the IEIS method are discussed.

  一种新型同位素编辑内部标准（IEIS）方法用于定量表面增强拉曼光谱（SERS），该方法使用了氘编辑的罗丹明6G（R6G-d0）和罗丹明6G（R6G-d4）。研究了IEIS方法在光学共振（SERRS）和非共振（SERS）条件下的可重复性和准确性。数据显示，在200 pM到2 μM的浓度范围内，批次间浓度测量的可重复性优于3%，并且分析物的浓度与其IEIS之间的差异可达3倍。通过与使用绝对SERS/SERRS强度校准（没有内部标准）或使用腺苷酸（而不是R6G-d4）作为罗丹明6G浓度定量的内部标准的结果进行比较，进一步展示了IEIS方法的优越性能。讨论了IEIS方法在生物医学基因表达和比较蛋白质组学应用中的潜力。
• Bi-analyte SERS with isotopically edited dyes
  作者：E. Blackie、E. C. Le Ru、M. Meyer、M. Timmer、B. Burkett、P. Northcote、P. G. Etchegoin

  DOI：10.1039/b803738h

  日期：——

  Isotopically substituted rhodamine dyes provide ideal probes for the study of single-molecule surface enhanced Raman scattering (SM-SERS) events through multiple-analyte techniques. Isotopic editing should, in principle, provide probes that have identical chemical properties (and surface chemistries); while exhibiting at the same time distinct Raman features which enable us to identify single-molecule SERS events. We present here a specific example of two-analyte SM-SERS based on the isotopic substitution of a methyl ester rhodamine dye. The dyes are carefully characterized (in both standard and SERS conditions) to confirm experimentally their similar chemical properties. We then demonstrate their utility for bi-analyte SERS (BiASERS) experiments and, as an example, highlight the transition from a single, to a few, to many molecules in the statistics of SM-SERS signals.

  同位素替代的罗丹明染料为通过多分析物技术研究单分子表面增强拉曼散射（SM-SERS）事件提供了理想的探针。从理论上讲，同位素编辑应该提供具有相同化学性质（和表面化学）的探针，同时展现出不同的拉曼特征，使我们能够识别单分子SERS事件。我们在这里提供一个基于甲基酯罗丹明染料同位素替代的双分析物SM-SERS具体示例。这些染料在标准条件和SERS条件下都经过仔细表征，以实验上确认它们相似的化学性质。然后，我们展示了它们在双分析物SERS（BiASERS）实验中的实用性，并以此为例突出单个分子、少量分子到大量分子在SM-SERS信号统计中的过渡。
• ISOTOPOLOGUES OF THALIDOMIDE
  申请人：Muller George W.

  公开号：US20120064004A1

  公开（公告）日：2012-03-15

  Provided herein are thalidomide, which is enriched with isotopes such as deuterium. Pharmaceutical compositions comprising the isotopes-enriched compounds, and methods of using such compounds are also provided.

  本文提供了富含氘等同位素的沙利度胺。还提供了包含这些同位素富集化合物的药物组合物以及使用这些化合物的方法。