3-叔丁基二甲硅氧基戊二酸酐 | 91424-40-7

• 物质功能分类: 化学试剂 - 有机试剂 - 羧酸酐
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 3-叔丁基二甲硅氧基戊二酸酐
• 中文别名: 3-(叔丁基二甲基硅氧基)戊二酸酐；3-TBDMSO戊二酸酐；3-叔丁基二甲基硅氧基戊二酸酐；瑞舒伐他汀钙中间体
• 英文名称: 3-(tert-butyldimethylsilyloxy)glutaric anhydride
• 英文别名: 4-(tert-butyldimethylsilyloxy)dihydro-2H-pyran-2,6(3H)-dione；deux références XF128 etr XF136；4-[tert-butyl(dimethyl)silyl]oxyoxane-2,6-dione
• CAS: 91424-40-7
• 化学式: C₁₁H₂₀O₄Si
• mdl: MFCD00075235
• 分子量: 244.363
• InChiKey: RXAJGRHLLRGVSB-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C(lit.)
• 沸点：
  302.4±35.0 °C(Predicted)
• 密度：
  1.030
• 闪点：
  >113°(235°F)
• 稳定性/保质期：
  避免接触强氧化剂

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(tert-Butyldimethylsilyloxy)glutaric anhydride
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-(tert-Butyldimethylsilyloxy)glutaric anhydride
CAS number: 91424-40-7

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.

---

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.
Storage: Store in closed vessels, refrigerated.

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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.

---

Section 9. Physical and chemical properties
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C11H20O4Si
Molecular weight: 244.4

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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, 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

制备方法与用途

应用领域广泛，3-叔丁基二甲硅氧基戊二酸酐可作为有机合成中间体和医药中间体，主要应用于实验室研发及医药化工生产中。

反应信息

• 作为反应物：
  描述：

  3-叔丁基二甲硅氧基戊二酸酐 在 palladium on activated charcoal 三乙基硅烷 、 sodium tetrahydroborate 、 Wilkinson's catalyst 、 氢氟酸 、 氢气 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 0.67h， 生成 美伐他汀
  参考文献：
  名称：

  康帕汀和相关化合物的合成和生物学研究。4. (+)-compactin 的全合成

  摘要：

  这些通过 Wadsworth-Emmons entre le t-丁基二甲基甲硅烷氧基-3 二甲氧基磷酰基-6 oxo-5 己酸酯 demethyle et l'hexahydro-1,2,6,7,8,8amethyl-2methyl-2'butyryloxy-8 的反应合成萘甲醛-1。应用程序合成 d'analoges

  DOI：

  10.1021/ja00298a062
• 作为产物：
  描述：

  1,3-丙酮二羧酸 在 咪唑 、 3% Ru/C 、 氢气 、 乙酸酐 作用下， 以 氯仿 为溶剂， 30.0 ℃ 、1.0 MPa 条件下， 反应 27.0h， 生成 3-叔丁基二甲硅氧基戊二酸酐
  参考文献：
  名称：

  Synthesis of 3-[(tert-Butyldimethylsilyl)oxy]glutaric Anhydride from Citric Acid

  摘要：

  从柠檬酸出发开发了一种新的3-[(叔丁基二甲基硅烷)氧]戊二酸酐的合成方法。柠檬酸是一种大宗化学品，每年通过发酵生产超过百万吨。这种新的合成路线展示了有效利用生物质资源合成瑞舒伐他汀中间体的方法。

  DOI：

  10.14233/ajchem.2014.16861

文献信息

• [EN] MODULATORS OF THE HISTAMINE H3 RECEPTOR AND THE TREATMENT OF DISORDERS RELATED THERETO<br/>[FR] MODULATEURS DU RÉCEPTEUR H3 HISTAMINIQUE ET TRAITEMENT DE TROUBLES S'Y RAPPORTANT
  申请人：ARENA PHARM INC

  公开号：WO2014028322A1

  公开（公告）日：2014-02-20

  The present invention relates to compounds of Formula (Ia) and pharmaceutically acceptable salts, solvates, and hydrates thereof, that modulate the activity of the histamine H3 receptor. Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of histamine H3-associated disorders.

  本发明涉及式(Ia)的化合物及其药用可接受的盐、溶剂和水合物，这些化合物调节组胺H3受体的活性。本发明的化合物和药物组合物用于治疗组胺H3相关疾病的方法。
• [EN] METHODS AND COMPOUNDS USEFUL IN TREATING PRURITUS, AND METHODS FOR IDENTIFYING SUCH COMPOUNDS<br/>[FR] MÉTHODES ET COMPOSÉS UTILES POUR TRAITER LE PRURIT, ET PROCÉDÉS D'IDENTIFICATION DESDITS COMPOSÉS
  申请人：ARENA PHARM INC

  公开号：WO2013151982A1

  公开（公告）日：2013-10-10

  The present invention relates to methods of using histamine 3 receptor (H3R) antagonists to treat pruritus or itch in an individual and methods for using H3R to screen for compounds capable of treating pruritus in an individual and methods for using pruritus/itch model systems for screening H3R antagonists for their usefulness in treating pruritus.

  本发明涉及使用组胺3受体（H3R）拮抗剂治疗个体的瘙痒或瘙痒的方法，以及使用H3R筛选能够治疗个体瘙痒的化合物的方法，以及使用瘙痒/瘙痒模型系统筛选H3R拮抗剂以评估其在治疗瘙痒方面的有效性的方法。
• CINCHONA-BASED BIFUNCTIONAL ORGANOCATALYSTS AND METHOD FOR PREPARING CHIRAL HEMIESTERS USING THE SAME
  申请人：SONG Choong Eui

  公开号：US20110213151A1

  公开（公告）日：2011-09-01

  The present invention relates to cinchona-based bifunctional organocatalysts and methods for preparing chiral hemiesters using the same. More specifically, the present invention relates to methods for preparing chiral hemiesters from prochiral or meso cyclic acid anhydrides via desymmetrization, using bifunctional cinchona alkaloid catalysts comprising sulfonamide functional groups.

  本发明涉及基于金鸡纳碱的双功能有机催化剂以及利用其制备手性半酯的方法。更具体地，本发明涉及利用含有磺酰胺功能团的双功能金鸡纳碱生催化剂，通过非对称化从原消旋或中性环酸酐制备手性半酯的方法。
• Enantioselective Alcoholysis of meso-Glutaric Anhydrides Catalyzed by Cinchona-Based Sulfonamide Catalysts
  作者：Sang Eun Park、Eun Hye Nam、Hyeong Bin Jang、Joong Suk Oh、Surajit Some、Yong Seop Lee、Choong Eui Song

  DOI：10.1002/adsc.201000289

  日期：2010.9.10

  The bifunctional Cinchona‐based sulfonamide catalysts showed the highest levels of enantioselectivity reported to date in the alcoholytic desymmetrization of meso‐glutaric anhydrides. Density functional theory (DFT) computational studies provide detailed insight into the observed sense of enantioselectivity. Moreover, detailed experimental studies and single crystal X‐ray analysis confirmed that these

  双功能金鸡纳为基础的磺胺催化剂表现出的对映选择性的最高水平的alcoholytic desymmetrization报告的日期观戊二酸酐。密度泛函理论（DFT）计算研究为观察到的对映选择性提供了详细的见识。此外，详细的实验研究和单晶X射线分析证实，这些双功能有机催化剂3在溶液和固态均不会形成H键结合的自聚集体。这种方法的合成效用还在合成重要的γ-氨基酸（例如（S）-普瑞巴林）中得到了证明。对映体纯（S的许多不对称合成）-迄今为止报道的普瑞巴林，我们的合成需要最少的步骤和最简单的步骤。
• 硅化合物的制造方法
  申请人：兰溪市立顺生物有限公司

  公开号：CN110407866A

  公开（公告）日：2019-11-05

  本发明提供硅化合物的制造方法，属于化学合成领域，包括如下工序：以柠檬酸为原材料进行氧化脱羧反应得到化合物1,3‑丙酮二羧酸；酯化反应得到化合物1,3‑丙酮二羧酸二甲酯；催化加氢还原得到化合物3‑羟基戊二酸二甲酯；醚化反应得到化合物3‑叔丁基二甲硅氧基戊二酸二甲酯；皂化反应、脱水反应、提纯得到化合物3‑叔丁基二甲硅氧基戊二酸酐；其中，催化加氢反应用催化剂为用沉淀还原法制得的Cu/ZnO/Al2O3。本发明对催化加氢的催化剂进行优化，使得加氢还原反应中，Cu催化剂的加氢活性显著提高，选择性增加，减少了副产物的产生；使用混合溶剂进行重结晶，产物收率和纯度显著提高。