(R)-N-BOC-4-氟苯甘氨酸 | 196707-32-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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: (R)-N-BOC-4-氟苯甘氨酸
• 中文别名: (R)-N-BOC-4-氟苯基甘氨酸
• 英文名称: (2R)-[(tert-butoxycarbonyl)amino](4-fluorophenyl)acetic acid
• 英文别名: (R)-2-((tert-butoxycarbonyl)amino)-2-(4-fluorophenyl)acetic acid；(R)-N-Boc-4-fluorophenylglycine；(2R)-2-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 196707-32-1
• 化学式: C₁₃H₁₆FNO₄
• 分子量: 269.273
• InChiKey: IEQBOUSLFRLKKX-SNVBAGLBSA-N

物化性质

• 熔点：
  85.7 °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：
  29224985

SDS

Name:	(R)-N-BOC-4-Fluorophenylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	(D)-N-tert-Butoxycarbonyl-alpha-(4-Fluorophenyl)Acetic Acid
CAS:	196707-32-1

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

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
196707-32-1	(R)-N-BOC-4-Fluorophenylglycine	95%	unlisted

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. 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.

---

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.

---

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. 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.

---

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# 196707-32-1: 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:
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: 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: 85.7 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: C13H16FNO4
Molecular Weight: 269.27

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 196707-32-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-N-BOC-4-Fluorophenylglycine - 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# 196707-32-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 196707-32-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 196707-32-1 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：

  (R)-N-BOC-4-氟苯甘氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.17h， 以91%的产率得到(R)-tert-butyl [1-(4-fluorophenyl)-2-hydroxyethyl]carbamate
  参考文献：
  名称：

  WO2008/5457

  摘要：

  公开号：
• 作为产物：
  描述：

  tert-butyl (4-fluorobenzyl)carbamate 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 3.33h， 生成 (R)-N-BOC-4-氟苯甘氨酸
  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

• Piperazine derivatives and the use thereof as medicament
  申请人：HOENKE Christoph

  公开号：US20150105397A1

  公开（公告）日：2015-04-16

  The present inventions relate to substituted piperazine derivatives of general formula (I) and to the manufacture of said compounds, pharmaceutical compositions comprising a compound according to general formula (I), and the use of said compounds for the treatment of various medical conditions related to glycine transporter-1 (GlyT1).

  这些发明涉及一般式(I)的取代哌嗪衍生物，以及所述化合物的制备，包括符合一般式(I)的化合物的药物组合物，以及利用这些化合物治疗与甘氨酸转运蛋白-1（GlyT1）相关的各种医疗状况。
• [EN] SUBSTITUTED PYRAZOLO[1,5-A]PYRIDINE COMPOUNDS AS RET KINASE INHIBITORS<br/>[FR] COMPOSÉS SUBSTITUÉS DE PYRAZOLO[1,5-A]PYRIDINE EN TANT QU'INHIBITEURS DE LA KINASE RET
  申请人：ANDREWS STEVEN W

  公开号：WO2018071447A1

  公开（公告）日：2018-04-19

  Provided herein are compounds of the Formula I and stereoisomers and pharmaceutically acceptable salts or solvates thereof, in which A, B, X1, X2, X3, X4, Ring D, and E have the meanings given in the specification, which are inhibitors of RET kinase and are useful in the treatment and prevention of diseases which can be treated with a RET kinase inhibitor, including RET-associated diseases and disorders.

  本文件提供了公式I的化合物以及立体异构体和药用可接受的盐或溶剂化物，其中A、B、X1、X2、X3、X4、环D和E具有说明书中给出的含义，它们是RET激酶的抑制剂，可用于治疗和预防可通过RET激酶抑制剂治疗的疾病，包括与RET相关疾病和失调。
• 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。
• [EN] PIPERAZINE DERIVATIVES AND THE USE THEREOF AS MEDICAMENT<br/>[FR] DÉRIVÉS DE PIPÉRAZINE ET LEUR UTILISATION EN TANT QUE MÉDICAMENT
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2015055698A1

  公开（公告）日：2015-04-23

  The present inventions relate to substituted piperazine derivatives of general formula (I) and to the manufacture of said compounds, pharmaceutical compositions comprising a compound according to general formula (I), and the use of said compounds for the treatment of various medical conditions related to glycine transporter-1 (GlyT1).

  这些发明涉及一般式(I)的取代哌嗪衍生物，以及制备该化合物、包含符合一般式(I)的化合物的药物组合物，以及利用该化合物治疗与甘氨酸转运蛋白-1（GlyT1）相关的各种医疗状况。
• Synthesis of <i>C</i>-Propargylic Esters of N-Protected Amino Acids and Peptides
  作者：Sean P. Bew、Glyn D. Hiatt-Gipson

  DOI：10.1021/jo100537q

  日期：2010.6.4

  critical importance of amino acids in organic synthesis as well as their myriad of applications in “click” chemistry it is interesting to note that the synthesis of C-propargyl derived amino acid esters has not been particularly well served. We report a convenient, straightforward, and high-yielding synthesis of structurally diverse C-propargyl-derived N-protected amino acid esters.

  近年来，人们对将炔烃衍生的基元用于所谓的“点击”化学反应产生了极大的兴趣。鉴于氨基酸在有机合成中的至关重要性及其在“点击”化学中的众多应用，值得注意的是，C-炔丙基衍生的氨基酸酯的合成并未得到很好的服务。我们报道了结构多样的C-炔丙基衍生的N-保护的氨基酸酯的方便，直接和高产率的合成。