(4R)-1-(tert-butyldimethylsilyl)-2-oxoazetidine-4-carboxylic acid | 82938-50-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硅烷
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4R)-1-(tert-butyldimethylsilyl)-2-oxoazetidine-4-carboxylic acid
• 英文别名: (R)-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid；(R)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylic acid；4-R-Carboxy-1-(t-butyldimethylsilyl)azetidinone；(2R)-1-[tert-butyl(dimethyl)silyl]-4-oxoazetidine-2-carboxylic acid
• CAS: 82938-50-9
• 化学式: C₁₀H₁₉NO₃Si
• 分子量: 229.351
• InChiKey: LIEWITJXZYCDLE-SSDOTTSWSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  309.3±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2933790090
• 安全说明：
  S24/25
• 储存条件：
  存放于0-6℃阴凉干燥处。

SDS

Name:	(4S)-N-(tert-Butyldimethylsilyl)azetidin-2-one-4-carboxylic acid 99% Material Safety Data Sheet
Synonym:
CAS:	82938-50-9

Section 1 - Chemical Product MSDS Name:(4S)-N-(tert-Butyldimethylsilyl)azetidin-2-one-4-carboxylic acid 99% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
82938-50-9	(4S)-N-(tert-Butyldimethylsilyl)azetid	99	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 82938-50-9: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: white - off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 135 - 137 deg C
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: C10H19NO3Si
Molecular Weight: 229.35

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 82938-50-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(4S)-N-(tert-Butyldimethylsilyl)azetidin-2-one-4-carboxylic acid - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 82938-50-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 82938-50-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 82938-50-9 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)-1-(tert-butyldimethylsilyl)-2-oxoazetidine-4-carboxylic acid 在 lithium diisopropyl amide 作用下， 反应 1.5h， 生成 (3S,4R)-1-(tert-butyldimethylsilyl)-3-ethyl-2-oxoazetidine-4-carboxylic acid
  参考文献：
  名称：

  人白细胞弹性蛋白酶的口服活性β-内酰胺抑制剂。3.3，3-二烷基氮杂环丁烷-2-酮的立体特异性合成和构效关系。

  摘要：

  描述了在es 3上几个4-[（4-羧基苯基）氧基] -3,3-二烷基-1-[[（（1-苯基烷基）-氨基]羰基]氮杂环丁烷-2-的立体有择合成，其中C- 3个烷基从甲基到丁基以及烯丙基，苄基和甲氧基甲基变化。讨论了这些化合物的结构活性关系，涉及β-内酰胺环的水解稳定性，它们对人白细胞弹性蛋白酶（HLE）的体外抑制能力以及它们在HLE介导的仓鼠肺出血中的体内口服功效分析。苄基脲部分上的进一步烷基取代，特别是在R构型中，提供了增强的HLE抑制和体内功效。（3R，4S）-4-[（（4-羧基苯基）氧基] -3-乙基-3-甲基-1-[[[（（R-1-1-苯基丙基）氨基]羰基]氮杂环丁烷-2-的立体化学分配一（42a）（穗/ [I] = 91，

  DOI：

  10.1021/jm00013a021
• 作为产物：
  描述：

  (2R)-benzyl N-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 生成 (4R)-1-(tert-butyldimethylsilyl)-2-oxoazetidine-4-carboxylic acid
  参考文献：
  名称：

  与ABT-594（一种有效的非阿片类镇痛药）相关的结构活性研究：吡啶和氮杂环丁烷环取代对小鼠烟碱型乙酰胆碱受体结合亲和力和镇痛活性的影响。

  摘要：

  制备了类似物A-98593（1）及其对映体ABT-594（2），在吡啶环上具有多个取代基，并测试了与大鼠脑中烟碱乙酰胆碱受体结合位点的亲和力以及在小鼠热板测定中的镇痛活性。多种修饰类型与对[3H]胱氨酸结合位点的高亲和力相一致。相比之下，仅选择的修饰导致止痛效果保持在与1和2相同的范围内。还制备了在氮杂环丁烷环的3位带有一个或两个甲基取代基的2的类似物，发现它们的活性实质上较低。两种测定。

  DOI：

  10.1016/s0960-894x(98)00504-6

文献信息

• Monocyclic β-lactam inhibitors of human leukocyte elastase
  作者：Raymond A Firestone、Peter L. arker、Judith M. isano、Bonnie M. she、Mary E. ahlgren

  DOI：10.1016/s0040-4020(01)82006-8

  日期：1990.1

  were designed to inactivate human leukocyte elastase (HLE) in three steps: first acylation of active-site serine; second, creation of a powerful new electrophilic center; third, covalent capture of a nucleophile from the enzyme. Both types do irreversibly inactivate HLE, and structure-activity relationships are in accord with the proposed mechanism. In each series, one molecule of the most active compound

  合成了两种类型的单环氮杂环丁酮，它们设计成通过三个步骤使人白细胞弹性蛋白酶（HLE）失活。第二，建立一个强大的新的亲电子中心；第三，从酶中共价捕获亲核试剂。两种类型均不可逆地使HLE失活，并且结构-活性关系与所提出的机制一致。在每个系列中，每20次遭遇中至少有1次分子中活性最高的化合物会抑制1个分子的HLE。
• Synthesis of (2,3)[4-2H3] valine: Application to the study of the ring expansion of penicillin N by deacetoxycephalosporin C synthase from Streptomyces clavuligerus
  作者：Jack E. Baldwin、Robert M. Adlington、Nicholas P. Crouch、Lisa C. Mellor、Nicholas Morgan、Alison M. Smith、John D. Sutherland

  DOI：10.1016/0040-4020(95)00126-s

  日期：1995.4

  [2′-2H3]-penicillin N via a chemico-enzymatic synthesis. This labelled penicillin was then used to demonstrate the stereospecific ring expansion of penicillin N to deacetoxycephalosporin C by deacetoxycephalosporin C synthase from Streptomyces clavuligerus.

  的一种新的合成（2 ，3 ）[4- 2 ħ 3 ]缬氨酸被开发，并用于合成（2 ）[2' - 2 ħ 3 ] -penicillinÑ通过一个化学-酶促合成。然后将该标记的青霉素用于证明青霉素N由脱乙酰选自C合成酶脱乙酰C中的有规立构环扩展小棒链霉菌。
• Bisphenyl compounds useful as vitamin D3 receptor agonists
  申请人：Wallace David

  公开号：US20060025474A1

  公开（公告）日：2006-02-02

  The present invention discloses bisphenyl compounds of the formula: wherein R1, R2, R3, R4, R5, R6, X, Y, W are defined herein after. These compounds are useful as pharmaceuticals.

  本发明公开了以下式子的双苯基化合物：其中R1，R2，R3，R4，R5，R6，X，Y，W的定义见下文。这些化合物可用作药物。
• Azetidinone derivatives for the treatment of HCMV infections
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US06242439B1

  公开（公告）日：2001-06-05

  A compound of formula I wherein R1 is hydrogen, methyl, ethyl, methoxy or methylthio; R2 and R3 each independently is hydrogen or lower alkyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy or benzyloxy; R5 is lower alkyl, lower cycloalkyl, (CH2)mC(O)OR6 wherein m is the integer 1 or 2 and R6 is lower alkyl, phenyl optionally substituted; optionally Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with C(O)O-benzyl or with phenyl optionally substituted with C(O)OR7 wherein R7 is lower alkyl or (lower alkyl)phenyl; and Z is lower alkyl or optionally substituted phenyl or Het; with the proviso that when Z is (CH2)p-(Het), then R2 and R3 each is hydrogen; or a therapeutically acceptable acid addition salt thereof which compound is useful in the treatment of HCMV infections.

  化合物I的化学式为：其中R1为氢、甲基、乙基、甲氧基或甲硫基；R2和R3各自独立地为氢或低碳基；R4为氢、低碳基、甲氧基、乙氧基或苄氧基；R5为低碳基、低环戊基、（CH2）mC（O）OR6，其中m为整数1或2，R6为低碳基、苯环可选择取代基；可选择为Het或Het（低碳基）；或者R4和R5与它们连接的氮原子一起形成含氮环，该环可选择取代为C（O）O-苄基或可选择取代为C（O）OR7的苯环，其中R7为低碳基或（低碳基）苯基；Z为低碳基或可选择取代的苯环或Het；但是当Z为（CH2）p-（Het）时，R2和R3各自为氢。该化合物或其治疗上可接受的酸盐在HCMV感染的治疗中有用。
• HETEROCYCLIC CETP INHIBITORS
  申请人：Salvati E. Mark

  公开号：US20070135631A1

  公开（公告）日：2007-06-14

  Compounds of formula Ia and Ib wherein A, B, C and R 1 are described herein.

  公式Ia和Ib的化合物，其中A、B、C和R1如下所述。