1-(N-叔丁氧羰基氨基)环己烷甲酸 | 115951-16-1

• 物质功能分类: 医药中间体
• 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: 1-(N-叔丁氧羰基氨基)环己烷甲酸
• 中文别名: 1-叔丁氧羰酰胺环己羧酸；丁氧羰基-1-氨基-1-环乙烷羧酸；1-叔丁氧基羰基氨基环己烷羧酸；1-(BOC-氨基)环己甲酸；1-((叔-丁氧羰基)氨基)环己羧酸；1-(Boc-氨基)环己羧酸；1-叔丁氧羰酰胺环己羧酸/1-(BOC-氨基)环己甲酸；Boc-1-氨基环己烷甲酸
• 英文名称: 1-tert-butoxycarbonylaminocyclohexanecarboxylic acid
• 英文别名: 1-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid；Boc-1-aminocyclohexane-1-carboxylic acid；1-(Boc-amino)cyclohexanecarboxylic acid；1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexane-1-carboxylic acid
• CAS: 115951-16-1
• 化学式: C₁₂H₂₁NO₄
• mdl: MFCD00273427
• 分子量: 243.303
• InChiKey: URBHKVWOYIMKNO-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C (dec.)
• 稳定性/保质期：
  如果遵照规格使用和储存，则不会分解，也未有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P280
• 危险性描述：
  H302+H312+H332
• 储存条件：
  密封保存，在0°C下应存放在冷藏环境中。

SDS

Name:	1-(tert-Butylcarbonyl)aminocyclohexanecarboxylic acid Material Safety Data Sheet
Synonym:	N-tert-Butylcarbonylaminocyclohexanecarboxylic acid
CAS:	115951-16-1

Section 1 - Chemical Product MSDS Name:1-(tert-Butylcarbonyl)aminocyclohexanecarboxylic acid Material Safety Data Sheet
Synonym:N-tert-Butylcarbonylaminocyclohexanecarboxylic acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
115951-16-1	1-(tert-Butylcarbonyl)aminocyclohexane	>97	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: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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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 appropriate 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. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. 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 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# 115951-16-1: 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: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 176.50-177.50 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: C12H21NO4
Molecular Weight: 243.3

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, amines, bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 115951-16-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(tert-Butylcarbonyl)aminocyclohexanecarboxylic 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
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 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 115951-16-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 115951-16-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 115951-16-1 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

制备方法与用途

制备

1-叔丁氧羰酰胺环己羧酸的制备如下：向圆底烧瓶中加入43 mL（4 mol/L）氢氧化钠溶液和40 mL四氢呋喃（THF），再滴加5.0 g（34.96 mmol）1-氨基环己烷甲酸。在0℃下，逐滴滴入9.13 g（41.96 mmol）二碳酸二叔丁酯，反应体系于室温搅拌过夜。随后加入100 mL水，并用50 mL（1 mol/L）盐酸酸化。接着使用乙酸乙酯进行萃取（共2次，每次50 mL），合并有机相后，再经饱和食盐水洗涤两次（每次100 mL）。有机相用无水硫酸钠干燥后过滤，并减压蒸馏去除溶剂，粗产物通过硅胶柱层析纯化（石油醚/乙酸乙酯体积比为4:1），最终得到白色固体标题化合物1-叔丁氧羰酰胺环己羧酸7.3 g，收率86%。

应用

1-叔丁氧羰酰胺环己羧酸可用作医药合成中间体。

危险处理

如吸入该物质，请将患者移至新鲜空气处；若皮肤接触，应立即脱去污染衣物，并使用肥皂水和清水彻底冲洗受影响区域，如有不适请就医；如果眼睛接触到该物质，需分开眼睑，用流动清水或生理盐水冲洗至少15分钟，随后立即就医；如吞食，请立即漱口并禁止催吐，随后立即就医。

反应信息

• 作为反应物：
  描述：

  1-(N-叔丁氧羰基氨基)环己烷甲酸 在 甲烷磺酸 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-氨基-N-(氰基甲基)环己烷甲酰胺
  参考文献：
  名称：

  探索组织蛋白酶B S2口袋的荧光特性的新型组织蛋白酶抑制剂：设计，合成和生物学评估

  摘要：

  氟还是氟？基于β，β-二氟环脂族氨基酸，新的二肽腈文库被评估为人组织蛋白酶抑制剂。通过分子建模和NMR研究阐明了氟化面相对于组织蛋白酶B蛋白质结构的方向（见图）。对于（R）配置的体，氟原子被定向到S 2凹穴，而在（S）配置的dis体中，氟化面暴露在溶剂中。

  DOI：

  10.1002/chem.201100113
• 作为产物：
  描述：

  1,3-二氮杂螺[4,5]癸烷-2,4-二酮 在 水 、 sodium hydroxide 、 barium(II) hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 87.0h， 生成 1-(N-叔丁氧羰基氨基)环己烷甲酸
  参考文献：
  名称：

  取代-1,3-二氮杂螺[4.5]癸烷-4-酮的合成及抗惊厥活性

  摘要：

  合成了一系列新型螺咪唑啉酮衍生物 6a-d 和 8a-x，并在最大电击癫痫 (MES) 试验和皮下戊四唑 (scPTZ) 筛选试验中对其抗惊厥活性进行了生物学评估。化合物 8w 是 scPTZ 筛选试验中活性最强的衍生物，其 ED50 值分别比作为参考药物的苯巴比妥和乙琥胺低约 5 倍和 83.6 倍。除了 8a 在 0.09 mmol/kg 下显示 100% 保护外，大多数测试化合物在 MES 筛选测试中表现出中等至微弱的活性。此外，所有测试化合物在神经毒性测试中均未表现出任何最小的运动损伤。

  DOI：

  10.1002/ardp.201500092
• 作为试剂：
  描述：

  2-二苯基膦-联苯 、 ethyl 2-(acetoxy(phenyl)methyl)acrylate 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 4-异丙基甲苯 、 三(4-甲氧苯基)膦 、 1-(N-叔丁氧羰基氨基)环己烷甲酸 、 sodium phosphate 作用下， 以 正己烷 为溶剂， 以75 %的产率得到ethyl (E)-2-((2'-(diphenylphosphino)-[1,1'-biphenyl]-2-yl)methyl)-3-phenylacrylate
  参考文献：
  名称：

  CN114478627

  摘要：

  公开号：

文献信息

• DIHYDROPYRIDAZINE-3,5-DIONE DERIVATIVE AND PHARMACEUTICALS CONTAINING THE SAME
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20160002251A1

  公开（公告）日：2016-01-07

  The present invention provides a dihydropyridazine-3,5-dione derivative or a salt thereof, or a solvate of the compound or the salt, a pharmaceutical drug, a pharmaceutical composition, a sodium-dependent phosphate transporter inhibitor, and a preventive and/or therapeutic agent for hyperphosphatemia, secondary hyperparathyroidism, chronic renal failure, chronic kidney disease, and arteriosclerosis associated with vascular calcification comprising the compound as an active ingredient, and a method for prevention and/or treatment.

  本发明提供了一种二氢吡啶嗪-3,5-二酮衍生物或其盐，或化合物或盐的溶剂化合物，一种药物，一种药物组合物，一种钠依赖性磷酸盐转运体抑制剂，以及作为活性成分的化合物的高磷血症、继发性甲状旁腺功能亢进症、慢性肾功能衰竭、慢性肾病和与血管钙化相关的动脉硬化的预防和/或治疗剂，以及预防和/或治疗的方法。
• Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders
  申请人：Georgetown University

  公开号：US07202279B1

  公开（公告）日：2007-04-10

  The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

  本发明提供了4-取代-2-氮杂环己酮化合物、双环2-5-二酮哌嗪化合物及其药物组合物，它们是有效、安全且有效的神经保护剂。由于它们具有强大的中枢神经系统（CNS）活性，这些化合物可用于增强记忆力并治疗各种神经系统疾病。这些化合物特别适用于治疗由中枢神经系统创伤引起或与之相关的神经系统疾病。
• Cu(I)-Catalyzed Synthesis of Dihydropyrimidin-4-ones toward the Preparation of β- and β³-Amino Acid Analogues
  作者：Basker Rajagopal、Ying-Yu Chen、Chun-Chi Chen、Xuan-Yu Liu、Huei-Ren Wang、Po-Chiao Lin

  DOI：10.1021/jo402670d

  日期：2014.2.7

  A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80–95%). The mild reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the stereochemistry. Further, by involving a variety

  已经成功地开发了铜（I）催化炔酮胺中间体从炔丙基酰胺合成取代的二氢嘧啶-4-酮。合成得到良好的分离产率（80-95％）。室温下温和的反应条件可使反应在数小时内完成，而无需改变立体化学。另外，通过涉及多种反应性亲核试剂，将得到的被取代的二氢嘧啶-4-酮被优雅转化成相应的β-和β 3 -氨基酸的类似物。
• Methods and compounds for inhibiting mrp1
  申请人：——

  公开号：US20030100576A1

  公开（公告）日：2003-05-29

  The present invention further relates to a method of inhibiting MRP1 in a mammal which comprises administering to a mammal in need thereof an effective amount of a compound of formula (I).

  本发明还涉及一种抑制哺乳动物中MRP1的方法，包括向需要的哺乳动物施用化合物(I)的有效量。
• Peptide‐Catalyzed Fragment Couplings that Form Axially Chiral Non‐ <i> C ₂ </i> ‐Symmetric Biaryls
  作者：Gavin Coombs、Marcus H. Sak、Scott J. Miller

  DOI：10.1002/anie.201913563

  日期：2020.2.10

  We have demonstrated that small, modular, tetrameric peptides featuring the Lewis-basic residue β-dimethylaminoalanine (Dmaa) are capable of atroposelectively coupling naphthols and ester-bearing quinones to yield non-C2 -symmetric BINOL-type scaffolds with good yields and enantioselectivity. The study culminates in the asymmetric synthesis of backbone-substituted scaffolds similar to 3,3'-disubstituted

  我们已经证明具有路易斯基本残基β-二甲基氨基丙氨酸（Dmaa）的小，模块化，四聚体肽能够对萘酚和带有酯的醌进行熵选择性偶联，以产生具有良好收率和对映选择性的非C2对称​​BINOL型支架。该研究最终以不对称合成类似于3,3'-双取代BINOL的骨架取代支架（如（R）-TRIP），重结晶后具有良好的（94：6 er）至优异的（> 99.9：0.1 er）对映选择性，以及修饰最小的非甾体类抗炎药（NSAID）萘普生的非对映选择性净芳基化。