(R)-4-苄基噻唑啉-2-硫酮 | 110199-17-2

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (R)-4-苄基噻唑啉-2-硫酮
• 中文别名: (R)-4-苄基噻唑-2-硫酮；(R)-4-苄基-1,3-噻唑烷-2-硫酮；R-4-苄基噻唑啉-2-硫酮
• 英文名称: (R)-4-benzylthiazolidine-2-thione
• 英文别名: (4R)-4-benzyl-1,3-thiazolidine-2-thione
• CAS: 110199-17-2
• 化学式: C₁₀H₁₁NS₂
• mdl: MFCD06658217
• 分子量: 209.336
• InChiKey: SLDUGQISGRPGAW-SECBINFHSA-N

物化性质

• 比旋光度：
  122 º (C=1% IN CHLOROFORM)
• 沸点：
  328.4±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• 海关编码：
  2934999090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : (R)-4-Benzylthiazolidine-2-thione

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a dangerous substance according to GHS.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C10H11NS2
Molecular Weight : 209,33 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
(R)-4-Benzylthiazolidine-2-thione
110199-17-2 - - - -

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Section 4. 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.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
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.

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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
Keep container tightly closed in a dry and well-ventilated place. Store in cool place.
Store under inert gas. Air sensitive.

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Personal protective equipment
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).
Hand 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.
Eye protection
Use equipment for eye protection tested and approved under appropriate government standards such as
NIOSH (US) or EN 166(EU).
Skin and 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.
Hygiene measures
General industrial hygiene practice.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form crystalline
Colour white
Safety data
pH no data available
Melting point no data available
Boiling point no data available
Flash point no data available
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Water solubility no data available
Partition coefficient: log Pow: 2,7
n-octanol/water

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Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
no data available
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx),
Sulphur oxides

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Section 11. TOXICOLOGICAL INFORMATION
Acute toxicity
no data available
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
no data available
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.
Additional Information
RTECS: Not available

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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
PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
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
ADR/RID
Not dangerous goods
IMDG
Not dangerous goods
IATA
Not dangerous goods

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Section 15. REGULATORY INFORMATION

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：该手性助剂具有高度的选择性和有效性，能够与二异丁基氢化铝发生还原裂解反应，直接还原生成相应的醛，并产生所需的手性助剂。

反应信息

• 作为反应物：
  描述：

  (R)-4-苄基噻唑啉-2-硫酮 在 4-二甲氨基吡啶 、 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 (3S)-hydroxy-1-((4R)-benzyl-2-thioxothiazolidin-3-yl)-7-tritylsulfanylhept-(4E)-en-1-one
  参考文献：
  名称：

  自由基介导的硫醇烯策略：癌细胞中含硫醇药物的光活化。

  摘要：

  光活化药物为治疗癌症等严重疾病提供了提高疗效并减少副作用的机会。本文描述了通过UV引发的硫醇-烯反应对异丁烯笼蔽的硫醇进行光活化解笼的方法。该方法通过异丁烯笼住的半胱氨酸、环状二硫肽和含硫醇的药物进行了论证，所有这些药物在硫醇源和光引发剂存在下，在温和的紫外线照射下都能快速有效地释放。重要的是，研究表明组蛋白脱乙酰酶抑制剂拉格唑的活性在缝合时可以关闭，但在用非光毒性光照射时在癌细胞内选择性地打开。

  DOI：

  10.1002/anie.201811338
• 作为产物：
  描述：

  1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone 在 四氯化钛 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.58h， 生成 (R)-4-苄基噻唑啉-2-硫酮
  参考文献：
  名称：

  Polyrhacitides A 和 B 的立体选择性全合成

  摘要：

  两种脂肪族聚酮化合物天然产物 polyrhacitides A 和 B，已以简洁且高度立体选择性的方式合成。该合成涉及基于辅助的乙酸醛醇反应以生成初始立体中心和迭代 Wittig 反应、分子内氧杂-迈克尔加成和螯合控制的还原反应作为生成额外立体中心的关键步骤。一锅酸介导的全局脱保护和环化反应形成最终的双环内酯核心。

  DOI：

  10.1002/ejoc.201100888

文献信息

• Synthesis and application of <i>N</i> ‐3,5‐dinitrobenzoyl and C ₃ symmetric diastereomeric chiral stationary phases
  作者：Jeong Jae Yu、Jae Jeong Ryoo

  DOI：10.1002/chir.23415

  日期：2022.4

  Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative chiral stationary phases (CSPs) (CSP 1, 2, and 3) and three C3 symmetric CSPs (CSP 4, 5, and 6). The six newly prepared CSPs were applied to the chiral

  三种非对映体手性化合物，即(R,R)-(+)-2-氨基-1,2-二苯乙醇、(1S,2R)-(+)-2-氨基-1,2-二苯乙醇和(1R) ,2R)-(+)-1,2-二苯基乙二胺作为起始原料制备三种N -3,5-二硝基苯甲酰基衍生物手性固定相 (CSPs) (CSP 1, 2, and 3) 和三种 C 3对称 CSPs （CSP 4、5 和 6）。将六种新制备的 CSP 应用于 HPLC 对 44 个手性样品的手性分离。大多数样品在 CSP 6 上分离，在六个新制备的 CSP 中平均分离因子最高。
• Total synthesis and structural validation of cyclodepsipeptides solonamide A and B
  作者：Betül Kitir、Mara Baldry、Hanne Ingmer、Christian A. Olsen

  DOI：10.1016/j.tet.2014.05.107

  日期：2014.10

  I (AIP-I). To enable more comprehensive studies, we embarked on the chemical synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereo-selective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures

  微生物是具有抗菌特性的新天然产物的诱人来源，海洋环境构成了生物活性微生物的丰富资源。在一项全球研究探险活动（Galathea III）中，从海洋细菌光致细菌耐盐细菌中分离出了两种depsipeptide，即solonamide A和solonamide B，并发现它们可抑制严重人类病原体金黄色葡萄球菌中的毒力基因表达。它们通过干扰农业群体感应系统来发挥作用，并显示出与内源性金黄色葡萄球菌的相似之处。群体感应肽，自动诱导肽I（AIP-1）。为了进行更全面的研究，我们着手化学合成了磺酰胺A和B。关键的合成步骤是通过立体选择性羟醛反应和环化大内酰胺化反应形成（R）-β-羟基脂肪酸。在高度稀薄的条件下。因此，solonamides的第一个全合成证实了最初分配的结构，并通过改变辅助的立体醛醇缩合步骤中，我们获得了对天然产品接入以及他们β 3差向异构体。
• Formation of Substituted Tetrahydropyrans through Oxetane Ring Opening: Application to the Synthesis of C1–C17 Fragment of Salinomycin
  作者：J. S. Yadav、Vinay K. Singh、P. Srihari

  DOI：10.1021/ol403604u

  日期：2014.2.7

  The stereoselective synthesis of C1–C17 fragment of salinomycin is achieved. The strategy employs a desymmetrization approach and utilizes an intramolecular oxetane opening reaction with O-nucleophile to result in the tetrahydropyran skeleton as the key step.

  达到了沙利霉素C1-C17片段的立体选择性合成。该策略采用去对称化方法，并利用与O-亲核试剂的分子内氧杂环丁烷开放反应来产生四氢吡喃骨架作为关键步骤。
• Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin
  作者：David S. Huang、Henry L. Wong、Gunda I. Georg

  DOI：10.1002/cmdc.201700084

  日期：2017.4.6

  addition into the natural product's α,β-unsaturated lactone. Although pironetin's α,β-unsaturated lactone is involved in its binding to tubulin, the structure-activity relationship at different positions of the lactone have not been thoroughly evaluated. For a systematic evaluation of the structure-activity relationships at the C4 and C5 positions of the α,β-unsaturated lactone of pironetin, twelve analogues

  吡咯丁酮是具有有效抗增殖活性的天然产物，可通过将缀合物加到天然产物的α，β-不饱和内酯中而与α-微管蛋白形成共价加合物。尽管吡咯丁酮的α，β-不饱和内酯参与了其与微管蛋白的结合，但是尚未充分评估内酯在不同位置的结构-活性关系。为了系统评价吡咯丁酮的α，β-不饱和内酯在C4和C5位的结构-活性关系，通过全合成制备了十二种天然产物的类似物。改变吡咯丁酮的α，β-不饱和内酯的C4和/或C5位置处的立体化学导致OVCAR5卵巢癌细胞中抗增殖活性的丧失。在用甲基等基团更改C4乙基取代基的同时，
• 硫唑啉-2-硫代酮的合成方法
  申请人：厦门本素药业有限公司

  公开号：CN111087361A

  公开（公告）日：2020-05-01

  本发明公开了一种硫唑啉‑2‑硫代酮的合成方法。本发明的如式IV所示的硫唑啉‑2‑硫代酮类化合物的合成方法包括如下步骤：(1)在溶剂中，将如式I所示的化合物与氯磺酸进行如下所示的成盐反应，得到如式II所示的化合物，即可；(2)在溶剂中，将如式II所示的化合物与如式III所示的化合物进行如下所示的环合反应，得如式IV所示的硫唑啉‑2‑硫代酮类化合物，即可；其中，R和R’独立地选自氢、C1‑6烷基、C6‑10芳基取代的C1‑6烷基、C6‑10芳基；R”为C1‑6烷基；M为碱金属。本发明的合成方法操作简单、产率较高且纯度较高。