(4S)-4-(叔丁基二甲基硅氧基)-2-吡咯烷酮 | 141629-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (4S)-4-(叔丁基二甲基硅氧基)-2-吡咯烷酮
• 英文名称: (S)-4-((tert-butyldimethylsilyl)oxy)pyrrolidin-2-one
• 英文别名: (4S)-4-((tert-butyl(dimethyl)silyl)oxy)pyrrolidin-2-one；(S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one；(4S)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidin-2-one
• CAS: 141629-19-8
• 化学式: C₁₀H₂₁NO₂Si
• 分子量: 215.368
• InChiKey: BEVGOGJIDJYUNN-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: (S)-4-(t-Butyldimethylsilyloxy)pyrrolidin-2-one
CAS number: 141629-19-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H21NO2Si
Molecular weight: 215.4

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (4S)-4-(叔丁基二甲基硅氧基)-2-吡咯烷酮 在 potassium phosphate 、 copper(l) iodide 、 硝酸 、 乙酸酐 、 N,N'-二甲基乙二胺 作用下， 反应 1.5h， 生成 (4S)-4-((tert-butyl(dimethyl)silyl)oxy)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one
  参考文献：
  名称：

  HETEROCYCLIC COMPOUND

  摘要：

  本发明提供了一种具有IRAK-4抑制作用的杂环化合物，该化合物对于预防或治疗炎症性疾病、自身免疫疾病、骨关节退行性疾病、肿瘤性疾病等具有用处，并且包含该化合物的药物。本发明涉及一种由下式（I）表示的化合物： 其中每个符号如规范中定义的那样，或其盐。

  公开号：

  US20150133451A1
• 作为产物：
  描述：

  (S)-4-azido-3-tert-butyldimethylsilyloxybutanal 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到(4S)-4-(叔丁基二甲基硅氧基)-2-吡咯烷酮
  参考文献：
  名称：

  Trials for the Synthesis of (R)-4-Mercapto-pyrrolidin-2-one ((R)-MPD)

  摘要：

  对(S)-4-羟基吡咯烷-2-酮（(S)-HPD）和(R)-4-巯基吡咯烷-2-酮（(R)-MPD）（口服活性碳青霉烯类抗生素 CS-834 的 2 位取代基）的合成进行了多次试验。后者是利用猪肝酯酶技术，从 3-对甲氧基苄基硫代戊二酸原手性二甲基或二乙基酯合成的，得到光学纯度为 51-71% 的单酯作为关键中间体。

  DOI：

  10.1055/s-1999-3111

文献信息

• Synthesis and Biological Evaluation of New Oral Carbapenems with 1-Methyl-5-oxopyrrolidin-3-ylthio Moiety.
  作者：OSAMU KANNO、MASAO MIYAUCHI、TAKAHIRO SHIBAYAMA、SATOSHI OHYA、ISAO KAWAMOTO

  DOI：10.7164/antibiotics.52.900

  日期：——

  The synthesis and biological properties of 1β-methylcarbapenems with 1-methyl-5-oxopyrrolidin-3-ylthio group at the C-2 position were studied. The sodium (1R, 5S, 6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(R)-1-methyl-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate and its (S)-isomer at the 2-position show potent and well-balanced antibacterial activity. The pharmacokinetic parameters of the pivaloyloxymethyl esters of these two carbapenems were compared in mice. The in vivo potency of these carbapenems was compared with that of cefdinir. Good in vivo efficacy of these ester prodrugs reflected the high and prolonged blood levels in parent drugs achieved after oral administration to mice.

  研究了在C-2位具有1-甲基-5-氧吡咯烷-3-基硫代基团的1β-甲基碳青霉烯化合物的合成及其生物学特性。在2-位具有(1R,5S,6S)-6-[(R)-1-羟基乙基]-1-甲基-2-[(R)-1-甲基-5-氧吡咯烷-3-基硫代]-1-碳青霉-2-烯-3-羧酸酯钠盐及其(S)-异构体的化合物显示出强效且平衡良好的抗菌活性。比较了这两种碳青霉烯化合物的特戊酰氧甲酯在小鼠中的药代动力学参数。这些碳青霉烯化合物在体内的效能与头孢地尼进行了比较。这些酯前药在体内的良好疗效反映了通过口服给药达到母药的高浓度和持续血药水平。
• [EN] AMIDE COMPOUNDS USEFUL IN THERAPY<br/>[FR] COMPOSÉS AMIDES UTILES EN THÉRAPIE
  申请人：PFIZER LTD

  公开号：WO2010032200A1

  公开（公告）日：2010-03-25

  A compound of Formula (I), or a pharmaceutically acceptable salt or solvate thereof, (I) wherein, R1 and R2 each independently represent H, halogen, CF3, C1-3 alkyl or C1-3 alkoxy; R3 represents C1-6 alkyl, C3-6 cycloalkyl, phenyl (optionally substituted by one or more substituents each independently selected from Ra) or Het (optionally substituted by one or more substituents each independently selected from OH, oxo, or C1-4 alkyl); R4 represents H or C1-3 alkyl; R5 represents C1-6 alkyl (optionally substituted by one or more substituents each independently selected from Rb), C3-6 cycloalkyl (optionally substituted by one or more substituents each independently selected from oxo or OH), or Het2 (optionally substituted by one or more substituents each independently selected from Rd); oxygen atom or 1 sulphur atom, or (c) 1 oxygen atom or 1 sulphur atom, (optionally substituted by one or more substituents each independently selected from OH, oxo or C1-4 alkyl); and R6 represents C1-3 alkyl (optionally substituted by one or more substituents each independently selected from Rf), C3-5 cycloalkyl (optionally substituted by one or more halogen), CN or halogen; where Rf represents halogen or phenyl: and compositions, processes for the preparation, and uses thereof, e.g. in the treatment of endometriosis or uterine fibroids.

  化合物的化学式（I），或其药学上可接受的盐或溶剂，其中，R1和R2分别独立表示H、卤素、CF3、C1-3烷基或C1-3烷氧基；R3表示C1-6烷基、C3-6环烷基、苯基（可选地由一个或多个Ra独立选择的取代基取代）或Het（可选地由一个或多个OH、氧代或C1-4烷基独立选择的取代基取代）；R4表示H或C1-3烷基；R5表示C1-6烷基（可选地由一个或多个Rb独立选择的取代基取代）、C3-6环烷基（可选地由一个或多个氧代或OH独立选择的取代基取代），或Het2（可选地由一个或多个Rd独立选择的取代基取代）；氧原子或1硫原子，或（c）1氧原子或1硫原子，（可选地由一个或多个OH、氧代或C1-4烷基独立选择的取代基取代）；和R6表示C1-3烷基（可选地由一个或多个Rf独立选择的取代基取代）、C3-5环烷基（可选地由一个或多个卤素取代）、CN或卤素；其中Rf表示卤素或苯基：以及其组合物、制备方法和用途，例如在子宫内膜异位症或子宫肌瘤的治疗中。
• 一种制备促智药物(S)-奥拉西坦的方法
  申请人：徐敏

  公开号：CN106349145B

  公开（公告）日：2018-11-20

  本发明公开了一种制备促智药物(S)‑奥拉西坦的方法，该方法包括如下步骤：1)在4‑二甲氨基吡啶催化下，将2‑环氧乙烷基乙酸异丁酯与氨气接触反应得到(S)‑4‑羟基‑2‑氧代吡咯烷；2)将步骤1)得到的(S)‑4‑羟基‑2‑氧代吡咯烷与叔丁基二甲基氯硅烷反应得到叔丁基二甲基硅保护的式III所示的化合物；3)式III所示的化合物在碱性条件下与2‑溴乙酸酯发生亲核反应得到式IV所示的化合物；4)在氯化铵催化下，式IV所示的化合物与氨气发生氨解反应得到(S)‑奥拉西坦；本发明的方法制备的(S)‑奥拉西坦收率高、ee值高并且成本较低，制备工艺简单适合工业化生产。
• Substrate-Controlled Chemoselective Reactions of Isocyanoacetates with Amides and Lactams
  作者：Jian-Feng Zheng、Xiu-Ning Hu、Zhen Xu、Dong-Cheng Cai、Tai-Long Shen、Pei-Qiang Huang

  DOI：10.1021/acs.joc.7b01768

  日期：2017.9.15

  Versatile and chemoselective C–C bond forming methods for the one-pot transformation of amides into other classes of compounds are highly demanding. In this report, we demonstrate the reductive addition of isocyanoacetates to common amides and lactams to produce 5-methoxyoxazoles or bicyclic imidazolines. This one-pot procedure involves partial reduction of amides with Schwartz reagent and chemoselective

  将酰胺一锅转化为其他类型化合物的通用且化学选择性的C–C键形成方法要求很高。在本报告中，我们证明了将异氰基乙酸酯还原加至常见的酰胺和内酰胺中，以产生5-甲氧基恶唑或双环咪唑啉。这种一锅法包括用Schwartz试剂将酰胺部分还原，以及在异氰基乙酸酯中化学选择性地添加异氰基基团的碳或α-碳。异氰基乙酸酯的完全不同的反应性是由于酰胺和内酰胺的空间位阻不同。
• Synthesis of nature product kinsenoside analogues with anti-inflammatory activity
  作者：Wei Song、Yong Sun、Lintao Xu、Yajing Sun、Tianlu Li、Peng Peng、Hongxiang Lou

  DOI：10.1016/j.bmc.2020.115854

  日期：2021.1

  medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated

  人参皂苷是来自草药的主要生物活性成分，具有广泛的药理功能。Goodyeroside A 是kinsenoside 的一种差向异构体，仍然很少被探索。在本报告中，我们化学合成了人参皂苷、Goodyeroside A 及其类似物，具有聚糖变异、手性中心的手性反转以及内酰胺对内酯的生物等排置换。在这些化合物中，goodyeroside A 及其甘露糖基对应物表现出优异的抗炎功效。此外，还发现枸杞苷 A 通过抑制 NF-κB 信号通路有效抑制炎症。还探索了构效关系，以进一步开发更有前途的人参皂苷类似物作为候选药物。