(S)-(-)-4-叔丁基氧氮杂环戊烷-2,5-二酮 | 62965-56-4

• 物质功能分类: 有机原料 - 酮类化合物
• 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: (S)-(-)-4-叔丁基氧氮杂环戊烷-2,5-二酮
• 中文别名: (S)-4-特丁基噁唑啉-2,5-二酮；N-Boc-L-叔亮氨酸；4-叔丁基氧氮杂环戊烷-2,5-二酮
• 英文名称: L-tert-butylglycine-N-carboxyanhydride
• 英文别名: L-tert-leucine N-carboxanhydride；(S)-4-tert-butyloxazolidine-2,5-dione；N-carboxy-t-leucine anhydride；L-tert-Leucine-N-carboxyanhydride；(S)-(-)-4-tert-Butyloxazolidine-2,5-dione；(4S)-4-tert-butyl-1,3-oxazolidine-2,5-dione
• CAS: 62965-56-4
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: GRDXOXRGSKKLNH-SCSAIBSYSA-N

物化性质

• 熔点：
  132°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 安全说明：
  S22,S24/25

SDS

Name:	L-tert-Leucine-N-Carboxyanhydride Material Safety Data Sheet
Synonym:	(S)-4-(1,1-Dimethylethyl)-2,5-Oxazolidinedione
CAS:	62965-56-4

Section 1 - Chemical Product MSDS Name:L-tert-Leucine-N-Carboxyanhydride Material Safety Data Sheet
Synonym:(S)-4-(1,1-Dimethylethyl)-2,5-Oxazolidinedione

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
62965-56-4	L-tert-Leucine-N-Carboxyanhydride	ca. 100	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
May cause skin irritation. May be 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:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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:

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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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Vacuum or sweep up material and place into a suitable, dry disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. 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:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 62965-56-4: 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 prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: sweetish odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 180 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: Slightly soluble.
Specific Gravity/Density:
Molecular Formula: C7H11NO3
Molecular Weight: 157.17

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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.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 62965-56-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
L-tert-Leucine-N-Carboxyanhydride - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Daphnia: Daphnia: EC50:>100mg/L; 24H-48H

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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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36 Irritating to eyes.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 39 Wear eye/face protection.
WGK (Water Danger/Protection)
CAS# 62965-56-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 62965-56-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 62965-56-4 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：

  (S)-(-)-4-叔丁基氧氮杂环戊烷-2,5-二酮 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 xylene 为溶剂， 反应 126.25h， 生成 (2R,5S)-2-Benzyl-5-tert-butyl-3,6-dimethoxy-2,5-dihydro-pyrazine
  参考文献：
  名称：

  Schoellkopf, Ulrich; Neubauer, Hans-Juergen, Synthesis, 1982, # 10, p. 861 - 864

  摘要：

  DOI：
• 作为产物：
  描述：

  光气 、 L-叔亮氨酸 生成 (S)-(-)-4-叔丁基氧氮杂环戊烷-2,5-二酮
  参考文献：
  名称：

  通过2,5-二酮哌嗪的金属化双内酰胺醚对非蛋白质氨基酸的对映选择性合成

  摘要：

  2,5-二酮哌嗪的双-内酯醚1包含一个手性诱导中心，一个酸性CH键和两个易于水解的位点。他们用BuLi反应以得到类型的锂化合物4，15，19或32，其具有前手性的C原子。他们很容易添加亲电试剂（例如烷基化剂或羰基化合物），具有非同寻常的非对映异构性。在许多情况下，加合物的减值（de =非对映异构体过量=不对称诱导）超过95％。水解时，加合物被裂解释放出手性助剂（用于构建双内酰胺醚1）和目标分子，即8型旋光氨基酸甲基酯，19，25或36。两种氨基酸酯可通过分馏或（最终在进一步水解成氨基酸后）通过色谱法分离。讨论了过渡状态模型，该模型可以解释异常高的不对称诱导和诱导构型的可预测性。

  DOI：

  10.1016/s0040-4020(01)91926-x

文献信息

• An Atom-Economical Method To Prepare Enantiopure Benzodiazepines with <i>N</i>-Carboxyanhydrides
  作者：Patrick S. Fier、Aaron M. Whittaker

  DOI：10.1021/acs.orglett.7b00417

  日期：2017.3.17

  development of a rapid, one-pot synthesis of diazepinones with simple reagents is described. N-Carboxyanhydrides (NCAs) are employed as amino acid building blocks that react with o-ketoanilines sequentially as electrophiles and nucleophiles to form diazepinones with water and carbon dioxide as byproducts. Notably, these reactions enable the coupling of stereodefined amino acid derived NCAs without racemization

  描述了用简单的试剂快速，一锅法合成二氮杂酮的进展。N-羧基氰化物（NCA）被用作氨基酸构建基，它们与邻-酮苯胺依次作为亲电子试剂和亲核试剂反应，以水和二氧化碳为副产物形成二氮杂蒽酮。值得注意的是，这些反应能够偶联立体定义的氨基酸衍生的NCA而无需消旋。通过向溴结构域和末端外（BET）溴结构域抑制剂的关键中间体的改进合成证明了该方法。
• Reactions of α-amino acid-N-carboxyanhydrides (NCAs) with organometallic palladium(0) and platinum(0) compounds: structure of a metallated NCA product and its role in polypeptide synthesis
  作者：Andrew A. Goodwin、Xianhui Bu、Timothy J. Deming

  DOI：10.1016/s0022-328x(99)00299-5

  日期：1999.10

  poly(γ-benzyl-l-glutamate) was formed in good yield, but with no control over polymer molecular weight. NMR studies showed that the N-carboxyanhydride ligand of 1 was responsible for polymerization initiation, which confirmed that metallated N-carboxyanhydrides, or ‘activated monomers’ are active, albeit inefficient, initiating species in NCA polymerizations.

  将Pt（COD）2和两当量的PEt 3与1-叔亮氨酸N-羧基酐反应，生成N = H氧化加成产物H（PEt 3）2 Pt （O）（1）。通过X射线晶体学确定1的结构和身份。的Pt（COD）2个两当量的PET的3也与N α -苄酯基-L-苯丙氨酸NCA得到OC 5氧化加成产物，（PET 3）2（2）。当1在室温下，将其与过量的γ-苄基-1-谷氨酸-N-羧基酐（Glu NCA）反应，以高收率形成聚（γ-苄基-1-谷氨酸），但不能控制聚合物的分子量。NMR研究表明1的N-羧基酸酐配体是引发聚合反应的原因，这证实了金属化的N-羧基酸酐或“活化单体”是活性的，尽管在NCA聚合中是无效的引发物种。
• Amino acid-n-carboxy anhydrides hvaing substituent at nitrogen
  申请人：——

  公开号：US20020173664A1

  公开（公告）日：2002-11-21

  This invention provides amino acid N-carboxyanhydrides, each of which has an N-acyl substituent on its nitrogen atom, is represented by the following formula (1): 1 readily reacts with nucleophilic reagents such as free amino acids, alcohols, anions or the like, and are intermediates useful for the high-yield production of amino acid derivatives, optically active compounds, peptides, polypeptides and the like useful in many fields lead by the fields of pharmaceuticals and agrochemicals, and also provides a process for the production of the amino acid N-carboxyanhydrides. Further, the present invention also provides a process for the production of diamides, which uses the compounds of the formula (1) and amine derivatives represented by the following formula (7): 2 These diamides can also be suitably used for the production of amino acid derivatives, optically active compounds, peptides, polypeptides and the like.

  本发明提供了氨基酸N-羧酸酐，每个酐都在其氮原子上具有N-酰基取代基，由以下公式（1）表示：1可以与自由氨基酸、醇、阴离子等亲核试剂轻松反应，是用于高产率生产氨基酸衍生物、光学活性化合物、肽、多肽等在制药和农化领域等多个领域有用的中间体，并提供了一种制备氨基酸N-羧酸酐的方法。此外，本发明还提供了一种使用公式（1）所述化合物和以下公式（7）所表示的胺衍生物的二酰胺的制备方法：2这些二酰胺也可适用于生产氨基酸衍生物、光学活性化合物、肽、多肽等。
• Process for the preparation of N-carboxy-t-leucine anhydride
  申请人：DSM N.V.

  公开号：US20010041812A1

  公开（公告）日：2001-11-15

  Process for the preparation of N-carboxy-t-leucine anhydride in which the corresponding N-carboxy-t-leucine is subjected to a cyclization with the aid of an acyl halogenide. Preferably, acetyl chloride is used as acyl halogenide. The N-carboxy-t-leucine anhydride obtained optionally is subsequently converted into a t-leucine-N-substituted amide with the aid of the corresponding amine. Preferably, methyl amine is chosen as the amine, and the reaction is carried out in a mixture of water and methanol as solvent.

  制备N-羧基-t-亮氨酸酐的过程中，使用酰卤化物协助进行相应的N-羧基-t-亮氨酸环化。最好使用乙酰氯作为酰卤化物。随后，可将所得的N-羧基-t-亮氨酸酐转化为t-亮氨酸-N-取代酰胺，使用相应的胺协助反应。最好选择甲基胺作为胺，并在水和甲醇的混合溶剂中进行反应。
• SUBSTITUTED IMIDAZOHETEROCYCLE DERIVATIVES
  申请人：O'Connor Stephen J.

  公开号：US20120015930A1

  公开（公告）日：2012-01-19

  The present invention provides substituted imidazoheterocycles having the general structure of formula I: wherein Y is chosen from —O—, —OCR g R h —, —CR g R h O—, —CR g R h —, —(CR g R h ) 2 —, —NR i —, —CR g R h NR i — and —NR i CR g R h —. Also provided are pharmaceutically acceptable salts, acid salts, hydrates, solvates and stereoisomers of the compounds of formula I. The compounds are useful as modulators of cannabinoid receptors and for the prophylaxis and treatment of cannabinoid receptor-associated diseases and conditions, such as pain, inflammation and pruritis.

  本发明提供了具有公式I的一般结构的取代咪唑杂环化合物，其中Y从—O—，—OCRgRh—，—CRgRhO—，—CRgRh—，—（CRgRh）2—，—NRi—，—CRgRhNRi—和—NRiCRgRh—中选择。此外，还提供了公式I化合物的药学上可接受的盐、酸盐、水合物、溶剂物和立体异构体。这些化合物可用作大麻素受体调节剂，并用于预防和治疗与大麻素受体相关的疾病和病症，例如疼痛、炎症和瘙痒。