(4R)-(+)-T-丁基二甲基硅氧-1-酮 | 61305-35-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: (4R)-(+)-T-丁基二甲基硅氧-1-酮
• 中文别名: 4-叔丁基二甲基硅氧基-2-环戊烯-1-酮；(R)-4-叔丁基二甲基硅氧基-2-环戊酮；4-叔丁基二甲硅氧基-2-环戊烯-1-酮
• 英文名称: (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone
• 英文别名: (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-one；4-(R)-(+)-tert-butyldimethylsilyloxy-2-cyclopenten-1-one；(4R)-(tert-butyldimethylsilyloxy)-cyclopent-2-en-1-one；(4R)-(+)-t-Butyldimethylsiloxy-2-cyclopenten-1-one；(4R)-4-[tert-butyl(dimethyl)silyl]oxycyclopent-2-en-1-one
• CAS: 61305-35-9
• 化学式: C₁₁H₂₀O₂Si
• 分子量: 212.364
• InChiKey: DAPZSGCXUJECAI-JTQLQIEISA-N

物化性质

• 熔点：
  26-28 °C
• 沸点：
  246.1±40.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 海关编码：
  2931900090
• 安全说明：
  S36/37
• 储存条件：
  存于阴凉干燥处

SDS

Name:	(R)-4-Tert-Butyldimethylsilyloxy-2-Cyclopenten-1-one 95% (98% E.E.) Material Safety Data Sheet
Synonym:	None Known
CAS:	61305-35-9

Section 1 - Chemical Product MSDS Name:(R)-4-Tert-Butyldimethylsilyloxy-2-Cyclopenten-1-one 95% (98% E.E.) Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
61305-35-9	(R)-4-Tert-Butyldimethylsilyloxy-2-Cyc	95%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
The toxicological properties of this substance have not been fully investigated.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 61305-35-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white to yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H20O2Si
Molecular Weight: 212.36

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, silicon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 61305-35-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-4-Tert-Butyldimethylsilyloxy-2-Cyclopenten-1-one - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 61305-35-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 61305-35-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 61305-35-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (4R)-(+)-T-丁基二甲基硅氧-1-酮 在 吡啶 、 copper(l) iodide 、 偶氮二异丁腈 、 三丁基膦 、 氢氟酸 、 叔丁基锂 、 三正丁基氢锡 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 6.5h， 生成 甲基前列腺素E1
  参考文献：
  名称：

  （-）-前列腺素E 1的简短合成

  摘要：

  （-）-前列腺素E 1由（-4 -）-丁基二甲基甲硅烷氧基-2-环戊烯酮通过串联有机铜共轭物加成/硝基烯烃迈克尔捕获所得烯醇酸酯中间体作为关键操作制备。

  DOI：

  10.1016/s0040-4039(00)88272-6
• 作为产物：
  描述：

  cis-3-acetoxy-5-pivaloxycyclopent-1-ene 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (4R)-(+)-T-丁基二甲基硅氧-1-酮
  参考文献：
  名称：

  Studies towards the total synthesis of an epoxy isoprostane phospholipid, a potent activator of endothelial cells

  摘要：

  我们报道了有关于环氧异前列腺素的总合成研究，即通过简单的三组分偶联法制备化合物9，该化合物是天然存在的环氧异前列腺素4的消除产物7的类比物，并通过几种光谱标准显示其与天然物质非常相似。

  DOI：

  10.1039/b209892j

文献信息

• Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling
  作者：Taehyeong Kim、Sung Il Lee、Sejin Kim、Su Yong Shim、Do Hyun Ryu

  DOI：10.1016/j.tet.2019.130593

  日期：2019.10

  The asymmetric total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig

  PGF的不对称全合成2α和-6,15-二酮PGF 1α和6-酮PGF的正式合成1α从一个共同的关键中间体进行说明。由（R）-4-甲硅烷氧基-2-环戊烯酮通过三组分偶联反应制备具有中间体的关键中间体，该中间体具有手性的环戊烷主链，该手性环戊烷主链具有合适的官能团且两侧链具有所需的立体化学。维悌希反应，野崎-桧山-岸（NHK）耦合和交叉复分解完成PGF的合成2α，-6,15-二酮PGF 1α和6-酮PGF 1α。
• THERAPEUTIC PROSTAGLANDIN RECEPTOR AGONISTS
  申请人：Allergan, Inc.

  公开号：US20150329518A1

  公开（公告）日：2015-11-19

  Described herein are compounds which can be used in topical liquids, creams, or other dosage forms such as solids, for reducing intraocular pressure, treating glaucoma, growing hair, treating wounds, or other medical and/or cosmetic uses.

  本文描述了可以用于局部液体、乳霜或其他剂型（如固体）中的化合物，用于降低眼内压、治疗青光眼、促进头发生长、治疗伤口或其他医疗和/或化妆用途。
• METHOD FOR INTRODUCING SUBSTITUENT INTO alpha,beta-UNSATURATED KETONE AND METHOD FOR SYNTHESIZING PROSTAGLANDIN USING THE SAME
  申请人：NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY

  公开号：US20210355061A1

  公开（公告）日：2021-11-18

  The present invention provides a method for introducing substituents into the α-position and the β-position of an α,β-unsaturated ketone, which not only can be used for the synthesis of a prostaglandin by a three-component coupling process, but also enables synthesis of a prostaglandin in a high yield by one-pot operation without requiring the use of a large excess amount of any of the three components required for the synthesis or using a highly toxic heavy metal as a catalyst or a solvent that is highly toxic to living bodies, and a method for synthesizing a prostaglandin using the same technical means. The method for introducing substituents into an α,β-unsaturated ketone according to the present invention is a method for introducing substituents into the carbon at the α-position and the carbon at the β-position of an α,β-unsaturated ketone, including: a first step of mixing alkyllithium and trialkylalkenyl tin in which tin atom binds to the vinyl position of the alkenyl group; a second step of mixing the mixture of the first step and dialkylzinc; a third step of mixing the mixture of the second step and an α,β-unsaturated ketone; and a fourth step of mixing the mixture of the third step and a trifluoromethanesulfonate compound.

  本发明提供了一种将取代基引入α，β-不饱和酮的α位和β位的方法，不仅可用于通过三组分偶联过程合成前列腺素，还能够通过一锅法高产率合成前列腺素，而无需使用大量超量的三种合成所需组分之一，也无需使用高毒性重金属作为催化剂或对生物体高毒的溶剂，并提供了一种利用相同技术手段合成前列腺素的方法。 根据本发明，将取代基引入α，β-不饱和酮的方法是一种将取代基引入α，β-不饱和酮的α位和β位碳的方法，包括：第一步，混合烷基锂和三烷基烯基锡，其中锡原子与烯基团的乙烯位结合；第二步，混合第一步的混合物和二烷基锌；第三步，混合第二步的混合物和α，β-不饱和酮；第四步，混合第三步的混合物和三氟甲磺酸盐化合物。
• Organozinc-aided, HMPA-free, stoichiometric three-component coupling for the general synthesis of prostaglandins and stable prostacyclin analogs with biological significance
  作者：Hiroko Koyama、Atsuto Izumiseki、Masaaki Suzuki

  DOI：10.1016/j.tetlet.2019.04.037

  日期：2019.5

  method afforded protected 5,6-didehydro-PGE2, a common intermediate for the general synthesis of natural PGs and the stable artificial prostacyclin (PGI2) analog isocarbacyclin in 88% yield. The utility of the method was further applied to the syntheses of novel intermediates, which are useful for the straightforward synthesis of 15R-TIC and 15-deoxy-TIC in 79% and 86% yield, respectively.

  通过结合二甲基锌辅助的ω-侧链乙烯基锂与（R）-4-羟基-的二甲基锌辅助共轭加成反应，开发了一种三组分偶联程序，以在无HMPA和化学计量条件下构建整个前列腺素（PG）骨架。2-环戊烯酮和用α-侧链炔丙基三氟甲磺酸酯直接捕获所得的烯醇化物。二甲基锌可有效调节共轭加成和炔基化反应。因此，该方法提供了受保护的5,6-didehydro-PGE 2，这是天然PG和稳定的人工前列环素（PGI 2的一般合成的通用中间体）类似异卡巴环素，收率88％。该方法的实用性进一步应用于新型中间体的合成，这些中间体可分别以79％和86％的收率直接合成15 R -TIC和15-脱氧-TIC。
• Et₃B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons
  作者：Masanori Nagatomo、Daigo Kamimura、Yuki Matsui、Keisuke Masuda、Masayuki Inoue

  DOI：10.1039/c5sc00457h

  日期：——

  three-component coupling reactions of sugar derivatives, without the need for light or heat. Et3B/O2-mediated decarbonylation readily converted α-alkoxyacyl tellurides to α-alkoxy carbon radicals, which intermolecularly added to glyoxylic oxime ether or enones to provide the two-component adducts. Furthermore, the three-component adducts were produced by an intermolecular aldol reaction between the aldehyde

  通过糖衍生物的基于自由基的二元和三元偶联反应，无需光或热，即可一步构建各种高氧碳骨架。Et 3 B/O 2介导的脱羰反应很容易将α-烷氧基酰基碲化物转化为α-烷氧基碳自由基，其分子间加成到乙醛肟醚或烯酮中以提供双组分加合物。此外，三组分加合物是通过醛和硼烯醇化物之间的分子间醛醇反应产生的，该反应是由 Et 3 B 捕获双组分自由基中间体产生的。这种强大的偶联方法是聚合合成多元醇天然产物。