1H-吲哚-2,3,4,5,6,7-d6 | 104959-27-5

• 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
• 中文名称: 1H-吲哚-2,3,4,5,6,7-d6
• 中文别名: 吲哚-d6；1H-吲哚-2,3,4,5,6,7-D6
• 英文名称: 1H-indole-d6
• 英文别名: 6-d6-indole；indole-d6；IND-d6；<2,3,4,5,6,7-D6>-Indol；2.3.4.5.6.7-Hexadeutero-indol；2,3,4,5,6,7-hexadeuterio-1H-indole
• CAS: 104959-27-5
• 化学式: C₈H₇N
• 分子量: 123.103
• InChiKey: SIKJAQJRHWYJAI-MZWXYZOWSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 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：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1H-吲哚-2,3,4,5,6,7-d6 、 2,3-二羟基苯甲酸甲酯 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 C₁₆H₈⁽²⁾H₅NO₄
  参考文献：
  名称：

  3-甲氧基羰基邻苯二酚和吲哚与芳基吲哚的氧化双向区域控制偶联

  摘要：

  3-甲氧基羰基儿茶酚通过苯碘 ( III )二乙酸酯氧化产生的邻苯醌中间体有效地与吲哚进行双向区域控制偶联，以在单-锅方式。DFT 计算证实了获得的区域选择性。

  DOI：

  10.1039/d2cc04843d
• 作为产物：
  描述：

  吲哚 在 10% Pt/activated carbon 、 重水 作用下， 以 环己烷 为溶剂， 以69%的产率得到1H-吲哚-2,3,4,5,6,7-d6
  参考文献：
  名称：

  3-甲氧基羰基邻苯二酚和吲哚与芳基吲哚的氧化双向区域控制偶联

  摘要：

  3-甲氧基羰基儿茶酚通过苯碘 ( III )二乙酸酯氧化产生的邻苯醌中间体有效地与吲哚进行双向区域控制偶联，以在单-锅方式。DFT 计算证实了获得的区域选择性。

  DOI：

  10.1039/d2cc04843d

文献信息

• Development of a Candidate Reference Method for the Simultaneous Quantitation of the Boar Taint Compounds Androstenone, 3α-Androstenol, 3β-Androstenol, Skatole, and Indole in Pig Fat by Means of Stable Isotope Dilution Analysis–Headspace Solid-Phase Microextraction–Gas Chromatography/Mass Spectrometry
  作者：Jochen Fischer、Paul W. Elsinghorst、Mark Bücking、Ernst Tholen、Brigitte Petersen、Matthias Wüst

  DOI：10.1021/ac201465q

  日期：2011.9.1

  The steroidal pig pheromones androstenone (5α-androst-16-en-3-one), 3α-androstenol (5α-androst-16-en-3α-ol), and 3β-androstenol (5α-androst-16-en-3β-ol) as well as the heterocyclic aromatic amines skatole and indole, originating from microbial degradation of tryptophan in the intestine of pigs, are frequently recognized as the major compounds responsible for boar taint. A new procedure, applying stable isotope dilution analysis (SIDA) and headspace solid-phase microextraction–gas chromatography/mass spectrometry (HS-SPME–GC/MS) for the simultaneous quantitation of these boar taint compounds in pig fat was developed and validated. The deuterated compounds androstenone-d3, 3β-androstenol-d3, skatole-d3, and indole-d6 were synthesized and successfully employed as internal standards for SIDA. The new procedure is characterized by a fast, simple, and economic sample preparation: methanolic extraction of the melted fat followed by a freezing and an evaporation step allows for extraction and enrichment of all five analytes. Additional time-consuming cleanup steps were not necessary, as HS-SPME sampling overcomes fat-associated injector and column contamination. The method has been validated by determining intra- and interday precision and accuracy as well as the limit of detection (LOD) and limit of quantitation (LOQ). Additionally, a cross-validation for androstenone, skatole, and indole was carried out comparing the results of 25 back fat samples obtained simultaneously by the new SIDA–HS-SPME–GC/MS procedure with those obtained in separate GC/MS and high-performance liquid chromatography fluorescence detection (HPLC-FD) measurements. The cross-validation revealed comparable results and confirms the feasibility of the new SIDA–HS-SPME–GC/MS procedure.

  猪类固醇信息素雄烯酮 (5α-androst-16-en-3-one)、3α-雄烯醇 (5α-androst-16-en-3α-ol) 和 3β-雄烯醇 (5α-androst-16-en-3β) -ol) 以及杂环芳香胺粪臭素和吲哚，源自猪肠道中色氨酸的微生物降解，通常被认为是造成公猪异味的主要化合物。开发并验证了一种新程序，应用稳定同位素稀释分析 (SIDA) 和顶空固相微萃取-气相色谱/质谱 (HS-SPME-GC/MS) 对猪脂肪中的这些公猪异味化合物进行同步定量。合成了氘化化合物雄烯酮-d3、3β-雄烯醇-d3、粪臭素-d3 和吲哚-d6，并成功用作 SIDA 的内标。新程序的特点是样品制备快速、简单且经济：对熔化的脂肪进行甲醇提取，然后进行冷冻和蒸发步骤，从而提取和富集所有五种分析物。不需要额外耗时的清理步骤，因为 HS-SPME 采样克服了与脂肪相关的进样器和色谱柱污染。该方法已通过确定日内和日间精密度和准确度以及检测限 (LOD) 和定量限 (LOQ) 进行了验证。此外，还对雄烯酮、粪臭素和吲哚进行了交叉验证，将通过新的 SIDA-HS-SPME-GC/MS 程序同时获得的 25 个背部脂肪样品的结果与单独 GC/MS 和高通量获得的结果进行比较。高效液相色谱荧光检测（HPLC-FD）测量。交叉验证揭示了可比较的结果，并证实了新的 SIDA-HS-SPME-GC/MS 程序的可行性。
• Anto, Sumathy; Getvoldsen, Gareth S.; Harding, John R., Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 11, p. 2208 - 2211
  作者：Anto, Sumathy、Getvoldsen, Gareth S.、Harding, John R.、Jones, John R.、Lu, Shui-Yu、Russell, Jeremy C.

  DOI：——

  日期：——
• Deuteration of indole and N-methylindole by Raney nickel catalysis
  作者：Wai-Ming Yau、Klaus Gawrisch

  DOI：10.1002/(sici)1099-1344(199907)42:7<709::aid-jlcr235>3.0.co;2-2

  日期：1999.7

  Indole and N-methylindole have been partially or fully deuterated by Raney nickel catalyzed H-1-H-2 exchange in a series of deuterated solvents. Perdeuterated indoles have been obtained in water and methanol while compounds that are preferentially deuterated at specific sites were obtained in chloroform, acetone, acetonitrile, ethanol, and isopropanol. The partially deuterated compounds are an important research tool for solid-state NMR studies on proteins.
• ORGANIC ELECTROLUMINESCENCE DEVICE
  申请人：TAKEDA Akira

  公开号：US20090058279A1

  公开（公告）日：2009-03-05

  An organic electroluminescent device includes a pair of electrodes; and an organic layer between the pair of electrodes, which includes a light-emitting layer and contains a compound represented by the following formula (1): wherein each of R 1 to R 7 independently represents a hydrogen atom or a substituent with the proviso that at least one of R 1 to R 7 represents a deuterium atom or a substituent containing a deuterium atom.
• US8012609B2
  申请人：——

  公开号：US8012609B2

  公开（公告）日：2011-09-06