丁氧羰基--环乙基-丙氨酸-羟基盐酸盐 | 37736-82-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 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: 丁氧羰基--环乙基-丙氨酸-羟基盐酸盐
• 中文别名: Boc-L-环己基丙氨酸；N-BOC-3-环己基-L-丙氨酸；BOC-L-环己基丙氨酸；(S)-2-叔丁氧羰基氨基-3-环己基丙酸
• 英文名称: (S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid
• 英文别名: Boc-Cha-OH；(2S)-2-(tert-butoxycarbonylamino)-3-cyclohexyl-propanoic acid；(S)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoic acid；Boc-L-cyclohexylalanine；Boc-cyclohexylalanine；(S)-α-[[(1,1-dimethylethoxy)-carbonyl]amino]cyclohexanepropanoic acid；N-(tert-butoxycarbonyl)-3-cyclohexyl-L-alanine；N-(tert-butoxycarbonyl)-L-cyclohexylalanine；Boc-L-Cha-OH；(2S)-3-cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 37736-82-6
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: MSZQAQJBXGTSHP-NSHDSACASA-N

物化性质

• 沸点：
  420.4±28.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：
  29242990
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  密封、阴凉、干燥保存。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Boc-Cha-OH hydrate
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 37736-82-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : Boc-hexahydro-L-phenylalanine
Boc-3-cyclohexyl-L-alaninehydrate
Formula : C14H25NO4 · xH2O
Molecular Weight : 271,35 g/mol
CAS-No. : 37736-82-6
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

(-2-((叔丁氧羰基)氨基)-3-环己基丙酸)是一种丙氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  丁氧羰基--环乙基-丙氨酸-羟基盐酸盐 在 lithium aluminium tetrahydride 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 2-甲基-2-丙基[(2S)-1-环己基-3-氧代-2-丙基]氨基甲酸酯
  参考文献：
  名称：

  二氟酮类肽模拟物提示阿尔茨海默氏病的γ-分泌酶有较大的S1口袋：这对抑制剂设计具有重要意义。

  摘要：

  与阿尔茨海默氏病的病因有关的淀粉样β蛋白（Abeta）的生成的最后一步是通过γ-分泌酶在淀粉样前体蛋白（APP）的跨膜区域内进行蛋白水解。尽管γ-分泌酶被认为是治疗设计的重要目标，但尚未被充分表征或确定。我们实验室中先前使用基于底物的二氟酮和二氟醇过渡态类似物抑制剂的研究表明，γ-分泌酶是天冬氨酰蛋白酶，具有宽松的序列特异性。为了进一步表征γ-分泌酶的活性位点，我们制备了一系列在P1位置具有不同空间体积的二氟酮肽类似物，并测试了这些化合物抑制APP转染细胞中Abeta产生的能力。庞大的脂肪族P1侧链（如仲丁基或环己基甲基）的引入导致增加的γ-分泌酶抑制能力，这表明一个大的S1口袋可容纳这些取代基，并为松散的序列特异性提供了进一步的证据。环己基甲基P1取代基可将N端截短为低分子量化合物（<600 Da），该化合物有效地阻断了Abeta的产生（IC（50）约为5 microM）。该发现表明，最

  DOI：

  10.1021/jm000100f
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 以98%的产率得到丁氧羰基--环乙基-丙氨酸-羟基盐酸盐
  参考文献：
  名称：

  （2S，4S，5S）-5-氨基-6-环己基-4-羟基-2-异丙基己酸正丁基酰胺的羟乙烯二肽异戊烯的合成

  摘要：

  描述了由Boc-L-苯丙氨酸立体选择性地合成（2S，4S，5S）-5-氨基-6-环己基-4-羟基-2-异丙基己酸正丁基酰胺的羟基亚乙基二肽等排体。

  DOI：

  10.1016/s0040-4039(00)91634-4

文献信息

• Interaction of Papain-like Cysteine Proteases with Dipeptide-Derived Nitriles
  作者：Reik Löser、Klaus Schilling、Elke Dimmig、Michael Gütschow

  DOI：10.1021/jm050686b

  日期：2005.12.1

  were introduced, and systematic fluorine, bromine, and phenyl scans for phenylalanine in the P2 position were performed. Moreover, the N-terminal protection was varied. Kinetic investigations were carried out with cathepsin L, S, and K as well as papain. Changes in the backbone structure of the parent N-(tert-butoxycarbonyl)-phenylalanyl-glycine-nitrile (16), such as the introduction of an R-configured

  制备一系列44个在P2位具有各种氨基酸和在P1位具有甘氨酸的二肽腈，并将其评估为半胱氨酸蛋白酶的抑制剂。关于P2-S2相互作用对酶抑制剂复合物形成的重要贡献，重点是将结构多样性引入P2侧链。引入了非蛋白氨基酸，并进行了系统的氟，溴和苯基扫描，以检测P2位置的苯丙氨酸。而且，N-末端保护是多种多样的。使用组织蛋白酶L，S和K以及木瓜蛋白酶进行动力学研究。母体N-（叔丁氧羰基）-苯丙氨酰基-甘氨酸-腈的骨架结构变化（16），例如将R构型的氨基酸或氮杂氨基酸引入P2以及P1氮的甲基化，会导致亲和力的急剧下降。示例性地，16的氰基被醛或甲基酮官能团取代。关于靶酶的底物特异性，讨论了构效关系。
• NOVEL SUBSTITUTED OCTAHYDROCYCLOPENTA[C]PYRROL-4-AMINES AS CALCIUM CHANNEL BLOCKERS
  申请人：Stewart Andrew O.

  公开号：US20100130558A1

  公开（公告）日：2010-05-27

  The present application relates to calcium channel inhibitors containing compounds of formula (I) wherein L 1 , L 2 , R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式（I）化合物的钙通道抑制剂，其中L1、L2、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• A Multicatalyst System for the One‐Pot Desymmetrization/Oxidation of <i>meso</i> ‐1,2‐Alkane Diols
  作者：Christian E. Müller、Radim Hrdina、Raffael C. Wende、Peter R. Schreiner

  DOI：10.1002/chem.201100498

  日期：2011.5.27

  Two is better than one: We demonstrate the viability of an organocatalytic reaction sequence along a short peptide backbone that carries two independent catalytic functionalities, which allow the rapid, one‐pot acylative desymmetrization and oxidation of meso‐alkane‐1,2‐diols to the corresponding acetylated acetoins with good yields and enantioselectivities (see scheme).

  两个优于一个：我们证明的有机催化反应序列的沿着承载两个独立的催化功能，其允许快速，一锅acylative desymmetrization和氧化的短肽骨架的生存能力内消旋-烷烃-1,2-二醇来具有良好产率和对映选择性的相应乙酰化乙酰丙酮（参见方案）。
• Synthesis of Cyclic Oligopeptides Containing an Arg-Gly-Asp (RGD) Sequence.
  作者：Shosuke SOFUKU、Akiko HOSHIDA、Takehiro SHIMADA、Yoichi TAKADA、Takashi TAKAKUWA

  DOI：10.1248/cpb.47.1799

  日期：——

  The synthesis of cyclic RGD peptides with 8-10 residues cyclized by an amide bond and the relationship between their structure and activity (i.e. circular dichroism spectrum and inhibition of platelet aggregation) are reported. The linear peptides were synthsized by the solution method and their cyclization was performed in high dilution using DPPA.

  报道了通过酰胺键环化的8-10个残基的环形RGD多肽的合成，以及它们的结构与活性（即圆二色谱和抑制血小板聚集）之间的关系。线性多肽是通过溶液法合成的，并在高稀释条件下使用DPPA进行环化。
• Immunoproteasome Inhibitor–Doxorubicin Conjugates Target Multiple Myeloma Cells and Release Doxorubicin upon Low-Dose Photon Irradiation
  作者：Elmer Maurits、Michel J. van de Graaff、Santina Maiorana、Dennis P. A. Wander、Patrick M. Dekker、Sabina Y. van der Zanden、Bogdan I. Florea、Jacques J. C. Neefjes、Herman S. Overkleeft、Sander I. van Kasteren

  DOI：10.1021/jacs.9b11969

  日期：2020.4.22

  are anthracyclines such as doxorubicin. We here present a new drug targeting approach that combines both drug classes into a single molecule. Doxorubicin was conjugated to an immunoproteasome-selective inhibitor via light-cleavable linkers, yielding peptide epoxyketone–doxorubicin prodrugs that remained selective and active toward immunoproteasomes. Upon cellular uptake and immunoproteasome inhibition

  蛋白酶体抑制剂是治疗血液系统癌症的公认治疗剂，蒽环类药物如阿霉素也是如此。我们在这里提出了一种新的药物靶向方法，它将两种药物类别结合到一个分子中。多柔比星通过光可裂解接头与免疫蛋白酶体选择性抑制剂偶联，产生肽环氧基酮-多柔比星前药，该前药对免疫蛋白酶体保持选择性和活性。在细胞摄取和免疫蛋白酶体抑制后，多柔比星通过光照射从免疫蛋白酶体抑制剂中释放出来。多发性骨髓瘤细胞以这种方式受到双重打击：免疫蛋白酶体抑制和阿霉素诱导的毒性。我们的策略需要靶向细胞毒剂，