肌氨酸酐 | 5076-82-4

• 物质功能分类: 生物化工 - 常见氨基酸及蛋白质类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 肌氨酸酐
• 英文名称: sarcosine anhydride
• 英文别名: 1,4-dimethyl-2,5-piperazinedione；1,4-dimethylpiperazine-2,5-dione；cyclo-sarcosylsarcosine；1,4-dimethyl-2,5-diketopiperazine
• CAS: 5076-82-4
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: PKDGRAULLDDTRN-UHFFFAOYSA-N

物化性质

• 熔点：
  144-147 °C(lit.)
• 沸点：
  259.72°C (rough estimate)
• 密度：
  1.2298 (rough estimate)
• 稳定性/保质期：
  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2933599090
• 储存条件：
  常温、避光、存放在阴凉干燥处并密封保存。

SDS

Name:	Sarcosine Anhydride 99% Material Safety Data Sheet
Synonym:	None Known
CAS:	5076-82-4

Section 1 - Chemical Product MSDS Name:Sarcosine Anhydride 99% Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5076-82-4	Sarcosine Anhydride	99%	225-788-5

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

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

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.
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:

---

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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

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.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 5076-82-4: 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 minimize contact with skin.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white to light beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 145.00 - 147.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H10N2O2
Molecular Weight: 142.16

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5076-82-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Sarcosine Anhydride - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

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# 5076-82-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5076-82-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5076-82-4 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  肌氨酸酐 在 二氯化二硫 、 水 、 三氯氧磷 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 二甲基-哌嗪四酮
  参考文献：
  名称：

  5,6-dicholoro-1,4-dihydro-1,4-dimethylpyrazine-2,3-dione的光重排及其进一步反应

  摘要：

  在uv上 辐照标题二酮（4）重排为2-（二氯亚甲基）-1,3-二甲基咪唑烷-4,5-二酮（7）（具有热可逆性）；然而，在湿气存在下，经由（6）形成二甲基咪唑烷三酮（5）。

  DOI：

  10.1039/c39810000743
• 作为产物：
  描述：

  N-甲基-2-羟基乙胺 在 Ru(H)(Cl)(PNNH(t-butyl))(CO) 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以99%的产率得到肌氨酸酐
  参考文献：
  名称：

  RUTHENIUM COMPLEXES AND THEIR USES AS CATALYSTS IN PROCESSES FOR FORMATION AND/OR HYDROGENATION OF ESTERS, AMIDES AND RELATED REACTIONS

  摘要：

  本发明涉及新型A1-A4式钌配合物及其用途，包括（1）醇的脱氢偶联制备酯；（2）酯的加氢制备醇（包括环酯（内酯）或环二酯（二内酯）的加氢，或聚酯的加氢）；（3）从醇和胺制备酰胺（包括通过二醇和二胺反应或氨基醇的聚合形成聚酰胺（例如，多肽），或从p-氨基醇形成环二肽）；（4）酰胺的加氢（包括环二肽、多肽和聚酰胺的加氢至醇和胺）；（5）有机碳酸酯（包括聚碳酸酯）的加氢至醇或羰基酸酯（包括聚羰基酸酯）或脲衍生物的加氢至醇和胺；（6）次级醇的脱氢至酮；（7）酯的酰胺化（即通过酯和胺合成酰胺）；（8）使用酯对醇进行酰化；（9）醇与水和碱的偶联形成羧酸；以及（10）通过氨基醇与水和碱的偶联制备氨基酸或其盐。本发明还涉及使用某些已知的钌配合物从氨基醇制备氨基酸或其盐。

  公开号：

  US20170283447A1
• 作为试剂：
  描述：

  2,4-二甲基-3-戊酮 在 肌氨酸酐 、 氘代丙酮 、 三乙胺 作用下， 反应 1344.0h， 生成 2-Deutero-2,4-dimethylpentanon-3
  参考文献：
  名称：

  吸电子基团和氢键对肽烯醇化物稳定性的远端影响

  摘要：

  已经计算了一系列乙酰胺、二酮哌嗪和线性二肽的相对气相碳酸度。结果表明，在这些系统中，N-吸电子取代基、质子化和酰胺氮上的氢键增加了与酰胺羰基相邻的 CH 质子和靠近酰胺氮的 CH 质子的酸度。两个位置的增加幅度之间存在良好的相关性，但与羰基相邻的远端 CH 的增加程度大于近端 CH 的增加程度，在大多数情况下约为两倍。显示对远端烯醇化物稳定性的影响主要是由诱导性影响引起的。这些效应的大小使得氮处的质子化和氢键使远端 CH 的酸度增加到几乎与羰基氧处的类似相互作用相同的程度。这种效应也出现在溶液中，其中与酰胺羰基相邻的 CH 计算出的水溶液 pK(a) 值更大，最多可达 13 个单位，并且初步实验研究表明酰胺的 N-乙酰化增加了通过形成相应的远端烯醇化物的氢-氘交换速率比通过近端烯醇化物、非乙酰化酰胺和二异丙基酮的交换速率高出 3 个数量级以上。结果还表明，在酶催化的 α-CH 键断裂中，与

  DOI：

  10.1021/ja100996z

文献信息

• <i>C</i>-Alkylation of <i>N</i>-alkylamides with styrenes in air and scale-up using a microwave flow reactor
  作者：Joshua P. Barham、Souma Tamaoki、Hiromichi Egami、Noriyuki Ohneda、Tadashi Okamoto、Hiromichi Odajima、Yoshitaka Hamashima

  DOI：10.1039/c8ob02282h

  日期：——

  N-alkylamides with styrenes is reported, proceeding in ambient air/moisture to give arylbutanamides and pharmaceutically-relevant scaffolds in excellent mass balance. Various amide and styrene derivatives were tolerated, rapidly affording molecular complexity in a single step; thus highlighting the future utility of this transformation in the synthetic chemistry toolbox. Reaction scalability (up to

  Ç的烷基化Ñ -alkylamides与苯乙烯报道，在环境空气中前进/水分，得到arylbutanamides和在良好的质量平衡的药学上相关的支架。可以耐受各种酰胺和苯乙烯衍生物，只需一步即可快速提供分子复杂性。因此，突出了这种转变在合成化学工具箱中的未来实用性。作为使用苯乙烯连续流动的C-烷基化反应的第一个实例，使用微波流反应器证明了反应可扩展性（高达65 gh -1产物）。
• Study of intramolecular aminolysis in peptides containing N-alkylamino acids at position 2
  作者：Vladimir V. Ryakhovsky、Andrey S. Ivanov

  DOI：10.1016/j.tet.2012.06.056

  日期：2012.9

  IA more strongly than aqueous ammonia, while tertiary amines were less effective. Peptides with methionine-S-oxide residues were more labile than the unoxidized analogs, suggesting intramolecular assistance of the S-oxide group in aminolysis. Surprisingly, intermediate compounds of the formula Boc–Met-MeXaa-Sar–NHR underwent rapid cleavage (endopeptolysis) upon attempted acidolytic deprotection.

  许多肽和蛋白质，含Ñ α -烷基氨基酸（包括脯氨酸）在所述第二位置，很容易发生分子内氨解（IA）具有N-末端二肽序列的消除2,5-二酮哌嗪（DKP）。我们合成了一系列短肽，在2位含有N-烷基氨基酸，并研究了它们在乙酸和胺存在下的稳定性。在第二侧链和第三个氨基酸残基，并且烷基化在存在Ñ α第三氨基酸残基的减慢IA。ñ α-第一个氨基酸残基中的烷基残基仅在包含三个或更多个残基的肽中阻碍IA。第一个氨基酸的侧链没有显着影响裂解率。乙酸比氨水对IA的促进作用更强，而叔胺的效果较差。具有蛋氨酸-S-氧化物残基的肽比未氧化的类似物更不稳定，这表明在氨解中S-氧化物基团的分子内辅助。出人意料的是，式Boc–Met-MeXaa-Sar–NHR的中间体化合物在尝试进行酸解脱保护后迅速裂解（内肽水解）。
• LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
  申请人：INTERMUNE, INC.

  公开号：US20140200215A1

  公开（公告）日：2014-07-17

  Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.

  提供的是化合物、制造这些化合物的方法、包含这些化合物的药物组合物和药品，以及使用这些化合物来治疗、预防或诊断与一个或多个溶血磷脂酸受体相关的疾病、失调或状况的方法。
• Studies in sulfur-nitrogen nucleophilicity
  作者：Marjorie C. Caserio、Jhong K. Kim

  DOI：10.1002/poc.3841

  日期：2018.8

  the ammonium salt from N‐methylation 2 dominated. The isomeric sulfonium salt 3 prepared by an independent route was found to be unstable and rearranged to the isomeric ammonium salt. The rearrangement pathway was investigated using deuterium‐labeled reactants. The sulfonium salt 3 also produced a piperazinium double salt 9 on heating. The reaction pathway was also followed by deuterium labeling. The

  作为研究氮与硫亲核试剂的一部分，描述了二甲基-（2-甲基硫乙基）胺CH 3 SCH 2 CH 2 N（CH 3）2 1的甲基化产物的行为。在两种潜在产物（sulf盐或铵盐）中，N-甲基化2的铵盐占主导地位。发现通过独立途径制备的异构sulf盐3是不稳定的，并且重排为异构铵盐。使用氘标记的反应物研究了重排途径。sulf盐3也产生了哌嗪复盐9在加热。反应路径之后还进行了氘标记。结果支持以下结论：复盐9的生产涉及N，N-二甲基叠氮鎓离子4的中间形成。
• Catalytic Hydrogenation for Producing Amines from Carboxylic Acid Amides, Carboxylic Acid Diamides, Di-, Tri-, or Polypeptides, or Peptide Amides
  申请人：Evonik Degussa GmbH

  公开号：US20160272571A1

  公开（公告）日：2016-09-22

  The present invention relates to a process for the preparation of amines, comprising the following steps: a. reaction of a (i) carboxylic acid amide of the general formula (I), or (ii) carboxylic acid diamide of the general formula (II), or (iii) di-, tri- or polypeptide, or (iv) peptide amide with carboxy-terminal amide function with an alkylating agent, b. addition of a hydrogenation catalyst to the reaction mixture in a molar ratio of from 1:10 to 1:100 000, based on carboxylic acid amide, carboxylic acid diamide, di-, tri- or polypeptide or peptide amide, c. reaction of the reaction mixture with hydrogen, where a hydrogen pressure of from 0.1 bar to 200 bar is established and where a temperature in a range of from 0° C. to 250° C. is established.

  本发明涉及一种氨基的制备方法，包括以下步骤：a. 将通式（I）的羧酸酰胺，或通式（II）的羧酸二酰胺，或二肽、三肽或多肽，或带有羧基末端酰胺功能的肽酰胺与烷基化剂发生反应，b. 在摩尔比为1:10至1:100,000的范围内向反应混合物中加入氢化催化剂，基于羧酸酰胺、羧酸二酰胺、二肽、三肽或多肽或肽酰胺，c. 将反应混合物与氢气反应，在此建立氢气压力为0.1巴至200巴，并在0°C至250°C的温度范围内进行反应。

表征谱图