6-(丙基硫代)嘌呤 | 6288-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 6-(丙基硫代)嘌呤
• 英文名称: 6-(propylthio)-9H-purine
• 英文别名: 6-propylsulfanyl-7(9)H-purine；6-(Propylthio)purine；6-propylsulfanyl-7H-purine
• CAS: 6288-93-3
• 化学式: C₈H₁₀N₄S
• mdl: MFCD08705743
• 分子量: 194.26
• InChiKey: BNLUVMLJJNTHSU-UHFFFAOYSA-N

物化性质

• 熔点：
  179 °C(Solv: water (7732-18-5))
• 沸点：
  105°C (rough estimate)
• 密度：
  1.2103 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Purine, 6-(propylthio)-
CAS-No. : 6288-93-3
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Nature of decomposition products not known.
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
no data available
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
LD50 Intraperitoneal - mouse - 92,88 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
Reproductive toxicity - rat - Oral
Effects on Fertility: Post-implantation mortality (e.g., dead and/or resorbed implants per total number of
implants).
Reproductive toxicity - rat - Intraperitoneal
Effects on Fertility: Post-implantation mortality (e.g., dead and/or resorbed implants per total number of
implants).
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: UO9082000

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-(丙基硫代)嘌呤 在 sodium acetate 、 溶剂黄146 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 dimethyl 2-phenyl-1-(6-(propylthio)-9H-purin-9-yl)cyclopent-3-ene-1,3-dicarboxylate
  参考文献：
  名称：

  通过MBH碳酸盐的α-嘌呤取代的丙烯酸酯的不对称[3 + 2]环状对映选择性地合成碳环核苷

  摘要：

  通过Morita-Baylis-Hillman（MBH）碳酸盐与α-嘌呤取代的丙烯酸酯的高度对映选择性[3 + 2]环化，已经建立了一种有效的途径来制备包含季立体中心和C═C双键的手性碳环核苷酸类似物。以20 mol％（S）-SITCP为催化剂，可以高收率（高达92％）和良好的非对映选择性（高达10：1 dr ）和极好的对映选择性（ee高达96％）。此外，将相应的产物进行各种转化以提供有趣的和潜在有用的手性碳环核苷。

  DOI：

  10.1021/acs.orglett.7b03625
• 作为产物：
  描述：

  溴丙烷 、 6-mercaptopurine 在 1-丁基-3-甲基-1H-咪唑-3-鎓三氟乙酸盐 作用下， 反应 24.0h， 以72%的产率得到6-(丙基硫代)嘌呤
  参考文献：
  名称：

  Modification of Thionucleobases in Ionic Liquids

  摘要：

  建立了一种简单的方法，使用室温离子液体（RTILs）如1-丁基-3-甲基咪唑三氟乙酸酯[BMIM]⁺[CF₃COO]⁻和1-甲氧基乙基-3-甲基咪唑三氟乙酸酯[MeOEtMIM]⁺[CF₃COO]⁻作为溶剂和催化剂，无需其他催化剂即可制备硫代嘌呤碱基。这些反应在RTILs中高效进行，产物收率极高。RTILs可以有效地回收和再利用，无需进一步纯化。

  DOI：

  10.1155/2014/353797

文献信息

• Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir
  作者：Tao Qin、Jian-Ping Li、Ming-Sheng Xie、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.joc.8b02442

  日期：2018.12.21

  nucleosides via Sharpless asymmetric dihydroxylation of N-allylpyrimidines or N-alkenylpurines is reported. A range of chiral acyclic nucleosides with two adjacent hydroxyl groups present on the side chains could be produced in good yields (up to 97% yield) and excellent enantioselectivities (90–99% ee). The synthetic utility of the reaction was demonstrated by the catalytic asymmetric synthesis of (S)-Cidofovir

  报道了一种通过N-烯丙基嘧啶或N-烯基嘌呤的Sharpless不对称二羟基化来构建手性无环核苷的有效方法。可以以高收率（最高97％的收率）和出色的对映选择性（90-99％ee）生产一系列在侧链上带有两个相邻羟基的手性无环核苷。通过（S）-西多福韦和（R）-比昔洛韦的催化不对称合成证明了该反应的合成效用。
• The Enantioselective Synthesis of Chiral Carbocyclic Nucleosides via Palladium‐Catalyzed Asymmetric Allylic Amination of Alicyclic MBH Adducts with Purines
  作者：Bo Kang、Qi‐Ying Zhang、Gui‐Rong Qu、Hai‐Ming Guo

  DOI：10.1002/adsc.202000088

  日期：2020.5.12

  The enantioselective synthesis of carbocyclic nucleosides through the palladium‐catalyzed asymmetric allylic amination of alicyclic Morita‐Baylis‐Hillman (MBH) adducts with purines was successfully developed. With a combination of Pd2(dba)3/L7 as catalyst, various optically active carbocyclic nucleosides featuring a C=C double bond in the carbocycle moiety were obtained in high yields (up to 97%) with

  通过钯催化的嘌呤与脂环式森田-贝利斯-希尔曼（MBH）加合物的钯催化不对称烯丙基胺化，成功开发了碳环核苷的对映选择性合成。结合使用Pd 2（dba）3 / L7作为催化剂，可以以高收率（高达97％）和优异的N 9 / N 7-获得各种在碳环部分具有C = C双键的旋光碳环核苷。选择性（> 95/5）和对映选择性（> 99.6％）。另外，这些核苷类似物允许快速转化为多种其他有趣的结构上不同的手性碳环核苷。
• A rapid and divergent access to chiral azacyclic nucleoside analogues via highly enantioselective 1,3-dipolar cycloaddition of β-nucleobase substituted acrylates
  作者：Qi-Liang Yang、Ming-Sheng Xie、Chao Xia、Huan-Li Sun、Dan-Jie Zhang、Ke-Xin Huang、Zhen Guo、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1039/c4cc06632d

  日期：——

  A rapid and divergent access to chiral azacyclic nucleoside analogues was developed via enantioselective 1,3-dipolar cycloaddition of β-nucleobase substituted acrylates.

  通过对β-核碱基取代丙烯酸酯进行对映选择性1,3-偶极环加成，开发了对手性氮杂环核苷类似物的快速和分歧访问。
• Highly Enantioselective Synthesis of Chiral Cyclopropyl Nucleosides via Catalytic Asymmetric Intermolecular Cyclopropanation
  作者：Jian-Ping Li、Guo-Feng Zhao、Hai-Xia Wang、Ming-Sheng Xie、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.orglett.7b03110

  日期：2017.12.15

  An efficient route to construct chiral cyclopropyl purine nucleoside analogues has been established via the catalytic asymmetric Michael-initiated ring-closure reactions of α-purine acrylates with α-bromo-carboxylic esters. Using (DHQD)2AQN as the catalyst, various chiral cyclopropyl purine nucleoside analogues with a chiral quaternary stereocenter were obtained in 72–98% yields, excellent diastereoselectivities

  通过α-嘌呤丙烯酸酯与α-溴代羧酸酯的催化不对称迈克尔引发的闭环反应，已经建立了构建手性环丙基嘌呤核苷类似物的有效途径。使用（DHQD）2AQN作为催化剂，可以获得具有手性四级立体中心的各种手性环丙基嘌呤核苷类似物，产率为72–98％，非对映选择性和93–97％ee。通过简单的官能团转化，获得具有羟甲基或羧基的多种手性环丙基嘌呤核苷。
• Regio- and Enantioselective Allylic Amination of Aliphatic MBH Adducts with N-Heteroaromatics
  作者：Haixia Wang、Lulu Yu、Mingsheng Xie、Jiang Wu、Guirong Qu、Kuiling Ding、Haiming Guo

  DOI：10.1002/chem.201704772

  日期：2018.1.26

  regio‐ and enantioselective allylic amination of aliphatic Morita‐Baylis–Hillman (MBH) adducts with N‐heteroaromatic nucleophiles (e.g., benzimidazole, 4,5‐diphenylimidazole, benzotriazole, and purines) was achieved by using a spiroketal‐based diphosphine (SKP) ligand, and afforded a range of chiral, branched N‐allyl products with high selectivity.

  脂族Morita-Baylis-Hillman（MBH）与N-杂芳族亲核试剂（例如苯并咪唑，4,5-二苯基咪唑，苯并三唑和嘌呤）的钯催化区域和对映选择性烯丙基胺化反应是通过使用基于螺酮基的二膦来实现的（SKP）配体，并提供了一系列具有高选择性的手性支化N烯丙基产品。

表征谱图