WO2018099271A1 - 一种制备氘代化学品的方法及氘代化学品 - Google Patents

一种制备氘代化学品的方法及氘代化学品 Download PDF

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WO2018099271A1
WO2018099271A1 PCT/CN2017/111314 CN2017111314W WO2018099271A1 WO 2018099271 A1 WO2018099271 A1 WO 2018099271A1 CN 2017111314 W CN2017111314 W CN 2017111314W WO 2018099271 A1 WO2018099271 A1 WO 2018099271A1
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substituent
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苏陈良
刘翠波
李瑛�
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Shenzhen University
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    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/057—Selenium or tellurium; Compounds thereof
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    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • the invention relates to the field of photocatalytic preparation of chemicals, in particular to a method for preparing deuterated chemicals and deuterated chemicals.
  • Deuterated chemicals are a special class of compounds that have important applications in the fields of reaction mechanism research, kinetics, drug metabolism and biological structure determination.
  • the heavy isotopes of hydrogen are usually introduced into the target compound by multi-step synthesis, and a variety of labeled chemical reagents will be involved in the process.
  • the hydroquinone catalytic exchange reaction is another very attractive strategy, in which the isotope is often introduced into the target molecule in one step.
  • the great challenge faced by this method is the selective control of hydroquinone exchange and the universality of functional groups. Most methods involve high temperatures, high pressures (helium is a source of helium), strong acids, strong bases or expensive metal catalysts.
  • the twisting reaction (or hydrazide reaction) has wider functional group adaptability and higher selectivity, and different twisting (or hydrazine) catalysts can be selected to achieve different functional sites.
  • the fixed point degeneration can be used as an ideal deuteration strategy.
  • the present invention aims to provide a method for preparing deuterated chemicals and deuterated chemicals, and to solve the existing twisting reaction (or decomposing reaction), which requires helium gas, As well as high temperature, high pressure and precious metal catalysts, the problem of the application range of the twisting reaction is greatly limited.
  • a method for preparing a deuterated chemical comprising the steps of: preparing a halogenated product by a light source, a photocatalyst, and a cerium source (in terms of molar mass ratio, hydrazine: halogenated substance: 1:1) Deuterated chemicals;
  • the hydrazine source is hydrophobic or deuterated solvent, and the reaction temperature is between -80 ° C and 150 ° C;
  • reaction formula is as follows: (1):
  • R is a carbon atom having a substituent
  • X is a halogen atom
  • D is a halogen atom
  • the method for preparing a deuterated chemical wherein the deuterated solvent is deuterated methanol, deuterated ethanol or deuterated acetone.
  • the method for preparing a deuterated chemical wherein the photocatalyst is a Ru, Ir containing catalyst, an organic dye catalyst, an inorganic semiconductor catalyst or an organic semiconductor catalyst.
  • the method for preparing a deuterated chemical wherein the light source is 200 to 2000 nm Light in any band.
  • a deuterated chemical prepared by the method of preparing a deuterated chemical as described above.
  • deuterated chemical wherein the deuterated chemical has a structure represented by the following formula (2):
  • R 1 to R 5 each independently represent a hydrogen atom, a halogen atom, a halogen atom, a carbon atom having a substituent, an oxygen atom having a substituent, a sulfur atom having a substituent, a nitrogen atom having a substituent, One of the phosphorus atoms having a substituent.
  • deuterated chemical wherein the deuterated chemical has a structure represented by the following formula (3):
  • R 1 to R 3 each independently represent a hydrogen atom, a halogen atom, a halogen atom, a carbon atom having a substituent, an oxygen atom having a substituent, a sulfur atom having a substituent, a nitrogen atom having a substituent, One of the phosphorus atoms having a substituent.
  • deuterated chemical wherein the deuterated chemical has a structure represented by the following formula (4):
  • R is a hydrogen atom, a halogen atom, a halogen atom, a carbon atom having a substituent
  • a substituent an oxygen atom having a substituent, a sulfur atom having a substituent, a nitrogen atom having a substituent, and a phosphorus atom having a substituent.
  • deuterated chemical wherein the deuterated chemical has one of the structures represented by the following formulas (5) to (7):
  • R 1 to R 3 each independently represent a hydrogen atom, a halogen atom, a halogen atom, a carbon atom having a substituent, an oxygen atom having a substituent, a sulfur atom having a substituent, and a substituent.
  • a nitrogen atom of a group and a phosphorus atom having a substituent One of a nitrogen atom of a group and a phosphorus atom having a substituent.
  • the present invention uses a hydrophobic or deuterated solvent instead of helium as a source of helium, achieving a mild twisting reaction.
  • Example 1 is a transmission electron micrograph of a photocatalyst cadmium selenide prepared in Example 1 of the present invention.
  • Example 2 is a graph showing the photohydrogen production performance of photocatalyst cadmium selenide prepared in Example 1 of the present invention.
  • Fig. 3 is a X-ray photoelectron spectroscopy chart showing the cadmium component of the photocatalyst cadmium selenide prepared in Example 1 of the present invention.
  • Example 4 is an X-ray photoelectron spectroscopy spectrum of a selenium component of a photocatalyst cadmium selenide prepared in Example 1 of the present invention.
  • the present invention provides a method for preparing deuterated chemicals and deuterated chemicals.
  • the following further details the present invention. Detailed description. It is understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
  • the present invention provides a preferred embodiment of a method for preparing a deuterated chemical, which comprises the steps of: halogenating a substance under the catalysis of a light source and a photocatalyst and a cerium source (in terms of molar mass ratio, hydrazine: halogenated substance > 1:1) ) performing a twisting reaction to produce a deuterated chemical;
  • the hydrazine source is hydrophobic or deuterated solvent, and the reaction temperature is between -80 ° C and 150 ° C (eg, 20 ° C, 60 ° C or 120 ° C);
  • reaction formula is as follows: (1):
  • R is a carbon atom having an arbitrary substituent
  • X is a halogen atom
  • D is a halogen atom
  • the hydrazine source of the present invention is a hydrophobic or deuterated solvent, and the deuterated solvent may be, but not limited to, deuterated methanol, deuterated ethanol or deuterated acetone.
  • the photocatalyst of the present invention may be, but not limited to, a catalyst containing Ru, Ir, an organic dye catalyst, an inorganic semiconductor catalyst or an organic semiconductor catalyst such as gC 3 N 4 .
  • the inorganic semiconductor catalyst may be, but not limited to, TiO 2 , CdS or CdSe.
  • the light source of the present invention may be, but not limited to, light of any wavelength band of 200 to 2000 nm (eg, 1000 nm).
  • the invention uses a hydrophobic or deuterated solvent instead of helium as a source of helium, and achieves a mild twisting (resolving) reaction, which effectively solves the problem that the existing helium reaction uses expensive helium gas and the reaction conditions are harsh, and the utility model is not practical. Sexual problem.
  • the present invention also provides a deuterated chemical, wherein the preparation is as described above Prepared by a method of deuterated chemicals.
  • the deuterated chemical of the present invention has the structural formula R-D; wherein R is a carbon atom having an arbitrary substituent, and D is a deuterium atom.
  • the deuterated chemical of the present invention may have a structure represented by the following formula (2) based on the structural formula of the above-described deuterated chemical:
  • R 1 to R 5 may each independently be a hydrogen atom, a halogen atom, a halogen atom, any carbon atom having a substituent, an oxygen atom having a substituent, a sulfur atom having a substituent, a nitrogen having a substituent.
  • R 1 to R 5 may each independently be a hydrogen atom, a halogen atom, a halogen atom, any carbon atom having a substituent, an oxygen atom having a substituent, a sulfur atom having a substituent, a nitrogen having a substituent.
  • the deuterated chemical of the present invention may have a structure represented by the following formula (3) based on the structural formula of the above-described deuterated chemical:
  • R 1 to R 3 may each independently represent a hydrogen atom, a halogen atom, a halogen atom, any carbon atom having a substituent, an oxygen atom having a substituent, a sulfur atom having a substituent, and a nitrogen having a substituent.
  • R 1 to R 3 may each independently represent a hydrogen atom, a halogen atom, a halogen atom, any carbon atom having a substituent, an oxygen atom having a substituent, a sulfur atom having a substituent, and a nitrogen having a substituent.
  • the deuterated chemical of the present invention may have a structure represented by the following formula (4) based on the structural formula of the above-described deuterated chemical:
  • R may be a hydrogen atom, a halogen atom, a halogen atom, or a substituent. Any one of a carbon atom, an oxygen atom having a substituent, a sulfur atom having a substituent, a nitrogen atom having a substituent, and a phosphorus atom having a substituent.
  • the deuterated chemical of the present invention may have one of the structures represented by the following formulas (5) to (7) based on the structural formula of the above-described deuterated chemical:
  • R 1 to R 3 may each independently represent a hydrogen atom, a halogen atom, a halogen atom, any carbon atom having a substituent, an oxygen atom having a substituent, a sulfur atom having a substituent, One of a nitrogen atom having a substituent and a phosphorus atom having a substituent.
  • the photocatalytic material is exemplified by two-dimensional cadmium selenide.
  • the preparation method is as follows:
  • FIG. 1 is a transmission electron micrograph of cadmium selenide nanosheets
  • FIG. 2 is a photocatalytic hydrogen production performance of cadmium selenide nanosheets
  • FIG. 3 is an X-ray photoelectron spectroscopy of cadmium components of cadmium selenide. X-ray photoelectron spectroscopy of selenium component of cadmium selenide.
  • the present invention provides a method for preparing deuterated chemicals and deuterated chemicals, and the present invention uses mild and inexpensive hydrophobic or deuterated solvents instead of helium to achieve highly selective twisting (
  • the reaction solves the problem that the use of expensive helium gas in the existing twisting reaction scheme and the harsh reaction conditions are not practical. Since the reaction conditions are more mild, the novel method of the invention can purify a series of chemicals, has the advantages of controllable and adjustable deuteration sites, and can reduce the preparation cost of deuterated chemicals, so that it is widely used in the reaction.

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Abstract

本发明的一种制备氘代化学品的方法及氘代化学品，其包括步骤：卤代物在光源、光催化剂催化下与氘源进行加氘反应，制得氘代化学品；其中，所述氘源为氘水或氘代溶剂，反应温度在-80℃～150℃之间。本发明以更环保、廉价的氘水或氘代试剂作氘源来代替氘气，以Ru，In金属催化剂、有机染料、无机和有机半导体纳米材料等为光催化剂在光催化的作用下实现对卤代物的氘解，提供一系列氘代化学品的精准可控制备。较传统的氘化反应具有更高的选择性、更温和的反应条件、更广的底物适应性以及更经济适用性，有望应用于大规模氘代化学品生产。

Description

一种制备氘代化学品的方法及氘代化学品 技术领域
本发明涉及光催化制备化学品领域，尤其涉及一种制备氘代化学品的方法及氘代化学品。
背景技术
氘代化学品是一类特殊化合物，在反应机理研究，动力学，药物代谢和生物结构测定等领域都有重要应用。氢的重同位素通常是通过多步合成引入目标化合物，过程中将涉及多种标记的化学试剂。氢氘催化交换反应则是另一种非常有吸引力的策略，过程中往往只需一步即可将同位素引入目标分子。该方法面临的巨大挑战在于氢氘交换的选择性控制以及官能团的普适性。绝大多数方法涉及高温、高压(氘气为氘源)、强酸、强碱或昂贵的金属催化剂。相对于氢氘催化交换反应，加氘反应(或氘解反应)具有更宽泛的官能团适应性和更高的选择性，选择不同的加氘(或氘解)催化剂，可以实现对不同官能位点进行定点氘化，可作为较理想的氘化策略。然而，由于加氘反应(或氘解反应)需要用到氘气，以及高温、高压和贵金属催化剂，大大限制了加氘反应的适用范围。
因此，现有技术还有待于改进和发展。
发明内容
鉴于上述现有技术的不足，本发明的目的在于提供及一种制备氘代化学品的方法及氘代化学品，旨在解决现有加氘反应(或氘解反应)需要用到氘气，以及高温、高压和贵金属催化剂，大大限制了加氘反应的适用范围的问题。
本发明的技术方案如下：
一种制备氘代化学品的方法，其中，包括步骤：卤代物在光源、光催化剂催化下与氘源(以摩尔质量比计，氘源∶卤代物>1∶1)进行加氘反应，制得氘代化学品；
其中，所述氘源为氘水或氘代溶剂，反应温度在-80℃～150℃之间；
反应式如下式(1)：
Figure PCTCN2017111314-appb-000001
式(1)中，R为具有取代基的碳原子，X为卤原子，D为氘原子。
所述的制备氘代化学品的方法，其中，所述氘代溶剂为氘代甲醇、氘代乙醇或氘代丙酮。
所述的制备氘代化学品的方法，其中，所述光催化剂为含Ru，Ir的催化剂、有机染料催化剂、无机半导体催化剂或有机半导体催化剂。
所述的制备氘代化学品的方法，其中，所述无机半导体催化剂为TiO2、CdS或CdSe。
所述的制备氘代化学品的方法，其中，所述光源为200～2000nm 任意波段的光。
一种氘代化学品，其中，采用如上任一所述的制备氘代化学品的方法制备而成。
所述的氘代化学品，其中，所述氘代化学品具有下述式(2)所示的结构：
Figure PCTCN2017111314-appb-000002
式(2)中，R1～R5分别为氢原子、氘原子、卤原子、具有取代基的碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
所述的氘代化学品，其中，所述氘代化学品具有下述式(3)所示的结构：
Figure PCTCN2017111314-appb-000003
式(3)中，R1～R3分别为氢原子、氘原子、卤原子、具有取代基的碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
所述的氘代化学品，其中，所述氘代化学品具有下述式(4)所示的结构：
Figure PCTCN2017111314-appb-000004
式(4)中，R为氢原子、氘原子、卤原子、具有取代基的碳原 子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
所述的氘代化学品，其中，所述氘代化学品具有下述式(5)～式(7)所示的结构中的一种：
Figure PCTCN2017111314-appb-000005
式(5)～式(7)中，R1～R3分别为氢原子、氘原子、卤原子、具有取代基的碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
有益效果：本发明以氘水或氘代溶剂来代替氘气作为氘源，实现了温和的加氘(氘解)反应。
附图说明
图1为本发明实施例1中制得的光催化剂硒化镉的透射电镜图。
图2为本发明实施例1中制得的光催化剂硒化镉的光解水产氢性能图。
图3为本发明实施例1中制得的光催化剂硒化镉的镉成份的X射线光电子能谱图。
图4为本发明实施例1中制得的光催化剂硒化镉的硒成份的X射线光电子能谱。
具体实施方式
本发明提供一种制备氘代化学品的方法及氘代化学品，为使本发明的目的、技术方案及效果更加清楚、明确，以下对本发明进一步详 细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
本发明提供一种制备氘代化学品的方法较佳实施例，其中，包括步骤：卤代物在光源、光催化剂催化下与氘源(以摩尔质量比计，氘源∶卤代物>1∶1)进行加氘反应，制得氘代化学品；
其中，所述氘源为氘水或氘代溶剂，反应温度在-80℃～150℃之间(如20℃、60℃或120℃)；
反应式如下式(1)：
Figure PCTCN2017111314-appb-000006
式(1)中，R为具有任意取代基的碳原子，X为卤原子，D为氘原子。
本发明所述氘源为氘水或氘代溶剂，所述氘代溶剂可以为但不限于氘代甲醇、氘代乙醇或氘代丙酮等。
本发明所述光催化剂可以为但不限于含Ru，Ir的催化剂、有机染料催化剂、无机半导体催化剂或有机半导体催化剂(如g-C3N4)。优选地，所述无机半导体催化剂可以为但不限于TiO2、CdS或CdSe。
本发明所述光源可以为但不限于200～2000nm(如1000nm)任意波段的光。
本发明以氘水或氘代溶剂来代替氘气作为氘源，实现温和的加氘(氘解)反应，有效解决了现有加氘反应中使用昂贵的氘气、反应条件苛刻等不具备实用性的问题。
本发明还提供一种氘代化学品，其中，采用如上任一所述的制备 氘代化学品的方法制备而成。
本发明所述氘代化学品的结构式为R-D；式中，R为具有任意取代基的碳原子，D为氘原子。
基于上述氘代化学品的结构式，本发明所述氘代化学品可以具有下述式(2)所示的结构：
Figure PCTCN2017111314-appb-000007
式(2)中，R1～R5可以分别为氢原子、氘原子、卤原子、具有取代基的任何碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
基于上述氘代化学品的结构式，本发明所述氘代化学品可以具有下述式(3)所示的结构：
Figure PCTCN2017111314-appb-000008
式(3)中，R1～R3可以分别为氢原子、氘原子、卤原子、具有取代基的任何碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
基于上述氘代化学品的结构式，本发明所述氘代化学品可以具有下述式(4)所示的结构：
Figure PCTCN2017111314-appb-000009
式(4)中，R可以为氢原子、氘原子、卤原子、具有取代基的 任何碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
基于上述氘代化学品的结构式，本发明所述氘代化学品可以具有下述式(5)～式(7)所示的结构中的一种：
Figure PCTCN2017111314-appb-000010
式(5)～式(7)中，R1～R3可以分别为氢原子、氘原子、卤原子、具有取代基的任何碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
下面通过实施例对本发明进行详细说明。
实施例1
(1)、光催化材料以二维硒化镉为例，其制备的方法如下：
用注射器将18毫摩尔硒粉分散液加入到冷却至室温的6.0毫摩尔CdCl2(辛胺，油胺)2复合物溶液中，将反应混合物缓慢加热到100摄氏度反应24小时后冷却到室温，停止搅拌；将反应混合物用乙醇洗涤、离心三遍，除掉大部分油胺，所得固体重新分散，离心，除掉大部分未反应的硒粉；再将所得二维硒化镉的氯仿溶液静止过夜，又有部分未反应的硒粉沉淀在瓶底，用移液枪将均匀分散的二维硒化镉的溶液转移到另外干净的圆底瓶中，并用酸性硅胶柱处理此溶液，样品反复用乙醇洗涤，得二维硒化镉纳米片固体样品，将此样品室温真空干燥备用。制得的硒化镉纳米片的表征见图1～图4所示。其中，图1为硒化镉纳米片的透射电镜图，图2为硒化镉纳米片的光解水产 氢性能图，图3为硒化镉的镉成份的X射线光电子能谱，图4为硒化镉的硒成份的X射线光电子能谱。
(2)、以氘水为氘源，光催化碘代芳烃的脱碘氘化反应如下：
分别称取0.1mmol碘代芳烃、5.0mg硒化镉纳米片和无水亚硫酸钠(0.125M)加入到50mL反应瓶中，并用注射器加入CH3CN/D2O混合溶液5.0mL，将反应体系置换为氩气保护状态，然后将反应瓶移动到距离光源中心10cm处光照反应2.0小时，反应结束后移走光源，将反应混合物用5.0mLCH2Cl2萃取，取2.0mL有机相并用无水硫酸钠干燥后进行GC-MS分析，并结合目标产物的标准曲线确定该反应的收率。上述总反应式见下式(8)所示，可生成的产物及其对应的收率见下式(9)～式(12)所示。
Figure PCTCN2017111314-appb-000011
Figure PCTCN2017111314-appb-000012
实施例2：制备氘代化学品
分别称取0.1mmol碘代芳烃、5.0mg硒化镉纳米片和无水亚硫酸钠(0.125M)加入到50mL反应瓶中，并用注射器分别加入CH3CN/D2O 5.0mL，将反应体系置换为氩气保护状态，然后将反应瓶移动到距离光源中心10cm处光照反应2.0小时，反应结束后移走光源，将反应混合物用CH2Cl2(5.0mL×3)萃取，合并有机相，用无水硫酸钠干燥，真空脱溶剂，柱层析分离得目标产物。所得产物经GC-MS,HRMS,H-NMR,C-NMR,FT-IR等测试确定结构。上述反应式及其对应产物的收率见下式(13)～式(14)所示。
Figure PCTCN2017111314-appb-000013
实施例3：光催化脱溴氘化制备氘代苯-d6
分别称取0.02mmol碘代芳烃、20.0mg硒化镉纳米片和无水亚 硫酸钠(0.50M)加入到50mL反应瓶中，并用注射器加入CH3CN/D2O(1：1,v/v)5.0mL，将反应体系脱气10分钟后置换为氩气保护状态，然后将反应瓶移动到距离光源中心10cm处光照反应2.0小时，反应结束后移走光源，将反应混合物用5.0mLCH2Cl2萃取，取2.0mL有机相并用无水硫酸钠干燥后进行GC-MS分析，并结合目标产物的标准曲线确定该反应的收率。上述反应式及其对应产物的收率见下式(15)所示。
Figure PCTCN2017111314-appb-000014
综上所述，本发明的一种制备氘代化学品的方法及氘代化学品，本发明使用了温和及廉价的氘水或氘代溶剂来代替氘气，实现高选择性的加氘(氘解)反应，解决了现有加氘反应方案中使用昂贵的氘气、反应条件苛刻等不具备实用性的问题。由于反应条件更加温和，本发明的新方法可氘化一系列化学品，具有氘化位点和个数可控、可调等优势，可降低氘代化学品制备成本，使其广泛应用于反应机理研究、动力学研究、药物代谢标定、生物分子标记等。
应当理解的是，本发明的应用不限于上述的举例，对本领域普通技术人员来说，可以根据上述说明加以改进或变换，所有这些改进和变换都应属于本发明所附权利要求的保护范围。

Claims (10)

  1. 一种制备氘代化学品的方法，其特征在于，包括步骤：卤代物在光源、光催化剂催化下与氘源进行加氘反应，制得氘代化学品；
    其中，所述氘源为氘水或氘代溶剂，反应温度在-80℃～150℃之间；
    反应式如下式(1)：
    Figure PCTCN2017111314-appb-100001
    式(1)中，R为具有取代基的碳原子，X为卤原子，D为氘原子。
  2. 根据权利要求1所述的制备氘代化学品的方法，其特征在于，所述氘代溶剂为氘代甲醇、氘代乙醇或氘代丙酮。
  3. 根据权利要求1所述的制备氘代化学品的方法，其特征在于，所述光催化剂为含Ru，Ir的催化剂、有机染料催化剂、无机半导体催化剂或有机半导体催化剂。
  4. 根据权利要求3所述的制备氘代化学品的方法，其特征在于，所述无机半导体催化剂为TiO2、CdS或CdSe。
  5. 根据权利要求1所述的制备氘代化学品的方法，其特征在于，所述光源为200～2000nm任意波段的光。
  6. 一种氘代化学品，其特征在于，采用如权利要求1～5任一所述的制备氘代化学品的方法制备而成。
  7. 根据权利要求6所述的氘代化学品，其特征在于，所述氘代化学品具有下述式(2)所示的结构：
    Figure PCTCN2017111314-appb-100002
    式(2)中，R1～R5分别为氢原子、氘原子、卤原子、具有取代基的碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
  8. 根据权利要求6所述的氘代化学品，其特征在于，所述氘代化学品具有下述式(3)所示的结构：
    Figure PCTCN2017111314-appb-100003
    式(3)中，R1～R3分别为氢原子、氘原子、卤原子、具有取代基的碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
  9. 根据权利要求6所述的氘代化学品，其特征在于，所述氘代化学品具有下述式(4)所示的结构：
    Figure PCTCN2017111314-appb-100004
    式(4)中，R为氢原子、氘原子、卤原子、具有取代基的碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
  10. 根据权利要求6所述的氘代化学品，其特征在于，所述氘代化学品具有下述式(5)～式(7)所示的结构中的一种：
    Figure PCTCN2017111314-appb-100005
    式(5)～式(7)中，R1～R3分别为氢原子、氘原子、卤原子、具有取代基的碳原子、具有取代基的氧原子、具有取代基的硫原子、具有取代基的氮原子、具有取代基的磷原子中的一种。
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