(S)-N-BOC-4-氟苯基氨基乙酸 | 142186-36-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - BOC-氨基酸
• 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)-N-BOC-4-氟苯基氨基乙酸
• 中文别名: (S)-N-BOC-4-氟代苯苷氨酸；(S)-N-Boc-4-氟苯基氨基乙酸
• 英文名称: (S)-2-((tert-butoxycarbonyl)amino)-2-(4-fluorophenyl)acetic acid
• 英文别名: (S)-N-Boc-4-fluorophenylglycine；(S)-[(tert-butoxycarbonyl)amino](4-fluorophenyl)acetic acid；(2S)-2-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 142186-36-5
• 化学式: C₁₃H₁₆FNO₄
• 分子量: 269.273
• InChiKey: IEQBOUSLFRLKKX-JTQLQIEISA-N

物化性质

• 熔点：
  130.2 °C
• 沸点：
  408.4±40.0 °C(Predicted)
• 密度：
  1.2168 (estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 海关编码：
  2922509090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Name:	(S)-N-BOC-4-Fluorophenylglycine, 95%, (98% E.E.) Material Safety Data Sheet
Synonym:	(L)-N-tert-Butoxycarbonyl-alpha-(4-Fluorophenyl)Acetic Acid.
CAS:	142186-36-5

Section 1 - Chemical Product MSDS Name: (S)-N-BOC-4-Fluorophenylglycine, 95%, (98% E.E.) Material Safety Data Sheet
Synonym: (L)-N-tert-Butoxycarbonyl-alpha-(4-Fluorophenyl)Acetic Acid.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
142186-36-5	(S)-N-BOC-4-Fluorophenylglycine	95%	unlisted

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

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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.

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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. 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. 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:
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 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. Clean up spills immediately, observing precautions in the Protective Equipment section. 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 breathing dust, vapor, mist, or gas. 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# 142186-36-5: 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:
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 to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 269.5 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C13H16FNO4
Molecular Weight: 269.27

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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:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 142186-36-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-BOC-4-Fluorophenylglycine - 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 Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material.

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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# 142186-36-5: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 142186-36-5 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 142186-36-5 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 1/16/2002 Revision #2 Date: 10/05/2004 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-N-BOC-4-氟苯基氨基乙酸 在 三乙胺 、 氯甲酸异丁酯 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以63%的产率得到(S)-N-(tert-butoxycarbonyl)-(4-fluorophenyl)glycinamide
  参考文献：
  名称：

  SUBSTITUIERTE PHENYLCYCLOHEXANCARBONSÄUREAMIDE UND IHRE VERWENDUNG ALS ADENOSINAUFNAHME-INHIBITOREN

  摘要：

  公开号：

  EP1187812B1
• 作为产物：
  描述：

  对氟苄胺 在 仲丁基锂 、 三乙胺 、 鹰爪豆碱 作用下， 以 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 6.33h， 生成 (S)-N-BOC-4-氟苯基氨基乙酸
  参考文献：
  名称：

  通过苄基锂化反应快速获得N- Boc苯基甘氨酸衍生物

  摘要：

  我们报告了一种新型有效的方法，用于N- Boc保护的苯基甘氨酸的对映选择性合成。产率和对映体比率根据溶剂，底物的性质和形成手性络合物的方法而有很大差异。结果表明，主要反应途径是对映选择性去质子化/取代过程。对映选择性似乎受s -BuLi-（-）-天冬氨酸络合物的手性鉴别能力的限制。所述的合成方法是获得有用的对映体富集的N- Boc苯基甘氨酸衍生物的最短途径之一。

  DOI：

  10.1016/s0040-4020(01)00159-4

文献信息

• [EN] INDANE DERIVATIVES AS MGLUR7 MODULATORS<br/>[FR] DÉRIVÉS D'INDANE UTILISÉS COMME MODULATEURS DE MGLUR7
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2017131221A1

  公开（公告）日：2017-08-03

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4a and R4b are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy. The compounds of formula (I) are mGluR7 modulators.

  本发明提供了式（I）的化合物及其药学上可接受的盐，其中R1、R2、R3、R4a和R4b如规范中定义，其制备方法，含有它们的药物组合物以及它们在治疗中的用途。式（I）的化合物是mGluR7调节剂。
• Design and Synthesis of Novel Anti-Proliferative Emodin Derivatives and Studies on their Cell Cycle Arrest, Apoptosis Pathway and Migration
  作者：Kun Yang、Ming-Ji Jin、Zhe-Shan Quan、Hu-Ri Piao

  DOI：10.3390/molecules24050884

  日期：——

  Emodin is a cell arrest and apoptosis-inducing compound that is widely distributed in different plants (rhubarb, aloe), lichens and terrestrial fungi, and also isolated from marine-derived fungi and marine sponge-associated fungi. In this study, we designed and synthesized a novel series of emodin derivatives by binding emodin to an amino acid using linkers of varying lengths and composition, and evaluated their anti-proliferative activities using HepG2 cells (human hepatic carcinoma), MCF-7 cells (human breast cancer) and human normal liver L02 cells. Most of these derivatives showed moderate to potent anti-proliferative activities. Notably, compound 7a exhibited potent anti-proliferative activity against HepG2 cells with the half maximal inhibitory concentration (IC50) value of 4.95 µM, which was enhanced 8.8-fold compared to the parent compound emodin (IC50 = 43.87 µM), and it also exhibited better selective anti-proliferative activity and specificity than emodin. Moreover, further experiments demonstrated that compound 7a displayed a significant efficacy of inducing apoptosis through mitochondrial pathway via release of cytochrome c from mitochondria and subsequent activation of caspase-9 and caspase-3, inducing cell arrest at G0/G1 phase, as well as suppression of cell migration of tumor cells. The preliminary results suggested that compound 7a could be a promising lead compound for the discovery of novel anti-tumor drugs and has the potential for further investigations as an anti-cancer drug.

  大黄素是一种引起细胞停滞和凋亡的化合物，广泛分布于不同植物（大黄、芦荟）、地衣和陆生真菌，同时也从海洋真菌和海绵相关真菌中分离出来。在这项研究中，我们设计并合成了一系列新型的大黄素衍生物，通过使用长度和组成不同的连接剂将大黄素与氨基酸结合，评估它们在HepG2细胞（人肝癌）、MCF-7细胞（人乳腺癌）和人正常肝细胞L02中的抗增殖活性。这些衍生物中大多数显示出中等到强效的抗增殖活性。值得注意的是，化合物7a对HepG2细胞表现出强效的抗增殖活性，半数抑制浓度（IC50）值为4.95 µM，比母体化合物大黄素（IC50 = 43.87 µM）提高了8.8倍，而且它还表现出比大黄素更好的选择性抗增殖活性和特异性。此外，进一步的实验表明，化合物7a通过线粒体途径释放细胞色素c并随后激活caspase-9和caspase-3诱导凋亡，使细胞在G0/G1期停滞，同时抑制肿瘤细胞的迁移。初步结果表明，化合物7a可能是发现新型抗肿瘤药物的有希望的先导化合物，并具有进一步作为抗癌药物进行研究的潜力。
• Heterocyclic Compound
  申请人：HASHIMOTO Kentaro

  公开号：US20110034469A1

  公开（公告）日：2011-02-10

  The present invention provides a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof. The compound of the present invention shows a strong IAP antagonistic activity.

  本发明提供了一种由下式表示的化合物 其中，每个符号如说明书中所定义，或其盐。本发明的化合物表现出强烈的IAP拮抗活性。
• [EN] NOVEL LACTAMS AND USES THEREOF<br/>[FR] NOUVELLES LACTAMES ET UTILISATIONS DE CES DERNIERES
  申请人：ASTRAZENECA AB

  公开号：WO2004031154A1

  公开（公告）日：2004-04-15

  Compounds having the formula (I) pharmaceutical compositions containing them and their methods of use for the treatment of neurological disorders related to amyloid ß protein production and neurological disorders such as Alzheimer's disease.. These compounds inhibit γ secretase and thereby inhibit the production of amyloid ß protein, thereby acting to prevent the formation of neurological deposits of amyloid protein.

  具有化学式（I）的化合物，含有它们的药物组合物以及它们用于治疗与淀粉样蛋白ß产生相关的神经系统疾病和阿尔茨海默病等神经系统疾病的方法。这些化合物抑制γ-分泌酶，从而抑制淀粉样蛋白ß的产生，从而防止神经系统中淀粉样蛋白的沉积形成。
• Chemo-Enzymatic Dynamic Kinetic Resolution of Amino Acid Thioesters
  作者：Dario Arosio、Antonio Caligiuri、Paola D'Arrigo、Giuseppe Pedrocchi-Fantoni、Cristina Rossi、Caterina Saraceno、Stefano Servi、Davide Tessaro

  DOI：10.1002/adsc.200700050

  日期：2007.6.4

  racemic-N-protected-β,γ-unsaturated α-amino acid thioesters were found to be substrates for the subtilisin-catalysed hydrolysis to the corresponding acids. The D-enantiomer was continuously racemised in the presence of an organic base. The combined reactions in a biphasic system allowed the deracemisation of the amino acid derivatives based on a dynamic kinetic resolution. Excellent yields and enantioselectivities

  发现外消旋-N-保护的β，γ-不饱和α-氨基酸硫代酯的L-形式是枯草杆菌蛋白酶催化水解成相应酸的底物。D-对映体在有机碱的存在下连续消旋。在双相系统中的合并的反应允许基于动态动力学拆分使氨基酸衍生物脱氨。获得了优异的产率和对映选择性。