二乙基(α-氨基苄基)膦酸酯 盐酸盐 | 16656-50-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 中文名称: 二乙基(α-氨基苄基)膦酸酯 盐酸盐
• 中文别名: 二乙基(Alpha-氨基苄基)磷羧酸盐酸；二乙基(α-氨基苄基)膦酸酯盐酸盐；二乙基 (Α-氨基苄基)磷羧酸盐酸
• 英文名称: diethyl 1-amino-1-phenylmethylphosphonate hydrochloride
• 英文别名: diethyl α-aminobenzylphosphonate hydrochloride；diethyl aminophenylmethyl phosphonate hydrochloride；Aminophenylmethanphosphonsaeurediethylesterhydrochlorid；diethoxyphosphoryl(phenyl)methanamine;hydron;chloride
• CAS: 16656-50-1
• 化学式: C₁₁H₁₈NO₃P*ClH
• 分子量: 279.704
• InChiKey: XMRSFMWMNXQRAP-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C (dec.)(lit.)
• 稳定性/保质期：
  按规定使用，该物质不会分解，并且能够避免氧化。

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2931900090
• 储存条件：
  存于密闭、阴凉、干燥处。

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: Diethyl (α-aminobenzyl)phosphonate hydrochloride
Product name
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. : 16656-50-1

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

---

SECTION 3: Composition/information on ingredients
Substances
Formula : C11H18NO3P · HCl
Molecular Weight : 279,70 g/mol
CAS-No. : 16656-50-1
No components need to be disclosed according to the applicable regulations.

---

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

---

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), Oxides of phosphorus
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

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.

---

SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
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)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

---

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.

---

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 191 °C - lit.
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

---

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

---

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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

---

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

---

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.

---

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

---

SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二乙基(α-氨基苄基)膦酸酯 盐酸盐 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 diethyl 1-aminophenylmethylphosphonate
  参考文献：
  名称：

  Synthesis and solution studies of Cu(II) complexes with pyridine derivatives of iminobisphosphonic acids

  摘要：

  New 2-pyridyl, 3-pyridyl and 4-pyridyl derivatives of iminobisphosphonic acid were prepared by addition of tris(trimethylsilyl) phosphite to the corresponding derivatives of pyridineimine-methylphosphonates 3 and subsequent methanolysis of the silylated products 4. Solution studies on the coordination abilities of the ligands have shown that these compounds bind copper(II) ion through the tridentate {N,O,O} mode, where Cu(II) is stabilized by two five-membered chelate rings. The complexes obtained are very stable, with the pCu(II) value above 12, and therefore the ligands can be used as powerful chelating agents for copper ion. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.09.045
• 作为产物：
  描述：

  苯甲醛吖嗪 在 甲醇 、 二乙基亚磷酸氢酯 、 四氯化钛 、 sodium hydride 作用下， 反应 29.0h， 生成 二乙基(α-氨基苄基)膦酸酯 盐酸盐
  参考文献：
  名称：

  Topolski, M.; Rachon, J., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 55, # 1-4, p. 97 - 110

  摘要：

  DOI：

文献信息

• [EN] BICYCLIC HETEROCYCLE DERIVATIVES AND USE THEREOF AS GPR119 MODULATORS<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES BICYCLIQUES ET LEUR UTILISATION EN TANT QUE MODULATEURS DE GPR119
  申请人：SCHERING CORP

  公开号：WO2009143049A1

  公开（公告）日：2009-11-26

  The present invention relates to Bicyclic Heterocycle Derivatives of formula (I), compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of GPR1 19 in a patient.

  本发明涉及公式（I）的双环杂环衍生物，包含双环杂环衍生物的组合物，以及使用双环杂环衍生物治疗或预防患者的肥胖、糖尿病、代谢紊乱、心血管疾病或与GPR119活性相关的疾病的方法。
• Lysine Acetylation in Sexual Stage Malaria Parasites Is a Target for Antimalarial Small Molecules
  作者：Katharine Trenholme、Linda Marek、Sandra Duffy、Gabriele Pradel、Gillian Fisher、Finn K. Hansen、Tina S. Skinner-Adams、Alice Butterworth、Che Julius Ngwa、Jonas Moecking、Christopher D. Goodman、Geoffrey I. McFadden、Subathdrage D. M. Sumanadasa、David P. Fairlie、Vicky M. Avery、Thomas Kurz、Katherine T. Andrews

  DOI：10.1128/aac.02721-13

  日期：2014.7

  Therapies to prevent transmission of malaria parasites to the mosquito vector are a vital part of the global malaria elimination agenda. Primaquine is currently the only drug with such activity; however, its use is limited by side effects. The development of transmission-blocking strategies requires an understanding of sexual stage malaria parasite (gametocyte) biology and the identification of new drug leads. Lysine acetylation is an important posttranslational modification involved in regulating eukaryotic gene expression and other essential processes. Interfering with this process with histone deacetylase (HDAC) inhibitors is a validated strategy for cancer and other diseases, including asexual stage malaria parasites. Here we confirm the expression of at least one HDAC protein in Plasmodium falciparum gametocytes and show that histone and nonhistone protein acetylation occurs in this life cycle stage. The activity of the canonical HDAC inhibitors trichostatin A (TSA) and suberoylanilide hydroxamic acid (SAHA; Vorinostat) and a panel of novel HDAC inhibitors on early/late-stage gametocytes and on gamete formation was examined. Several compounds displayed early/late-stage gametocytocidal activity, with TSA being the most potent (50% inhibitory concentration, 70 to 90 nM). In contrast, no inhibitory activity was observed in P. falciparum gametocyte exflagellation experiments. Gametocytocidal HDAC inhibitors caused hyperacetylation of gametocyte histones, consistent with a mode of action targeting HDAC activity. Our data identify HDAC inhibitors as being among a limited number of compounds that target both asexual and sexual stage malaria parasites, making them a potential new starting point for gametocytocidal drug leads and valuable tools for dissecting gametocyte biology.

  摘要 防止疟原虫向蚊媒传播的疗法是全球消除疟疾议程的重要组成部分。伯氨喹是目前唯一具有这种活性的药物，但其使用受到副作用的限制。要开发阻断传播的策略，就必须了解有性阶段疟原虫（配子体）的生物学特性，并找出新的药物线索。赖氨酸乙酰化是一种重要的翻译后修饰，参与调节真核基因表达和其他重要过程。用组蛋白去乙酰化酶（HDAC）抑制剂干扰这一过程是治疗癌症和其他疾病（包括无性阶段的疟原虫）的有效策略。在这里，我们证实了恶性疟原虫中至少有一种 HDAC 蛋白的表达。 恶性疟原虫 配子细胞中至少有一种 HDAC 蛋白的表达，并表明组蛋白和非组蛋白乙酰化发生在这一生命周期阶段。研究考察了典型 HDAC 抑制剂 trichostatin A (TSA) 和 suberoylanilide hydroxamic acid (SAHA; Vorinostat) 以及一系列新型 HDAC 抑制剂对早期/晚期配子细胞和配子形成的活性。有几种化合物显示出早期/晚期配子细胞杀伤活性，其中 TSA 的杀伤活性最强（50% 抑制浓度，70 至 90 nM）。相比之下，在恶性疟原虫中没有观察到抑制活性。 恶性疟原虫 配子细胞外排实验中未观察到抑制活性。配子细胞杀伤性 HDAC 抑制剂会引起配子细胞组蛋白的高乙酰化，这与针对 HDAC 活性的作用模式是一致的。我们的数据表明，HDAC抑制剂是少数同时针对无性和有性阶段疟原虫的化合物之一，因此它们可能成为配子细胞杀灭药物的新起点，也是研究配子细胞生物学的宝贵工具。
• SYNTHESIS OF PHOSPHONOPEPTIDES CONTAINING 1-AMINOALKYLPHOSPHONIC ACID
  作者：Jiaxi Xu、Chengfeng Xia、Li Yu、Qingzhong Zhou

  DOI：10.1080/10426509908031615

  日期：1999.9.1

  phosphonate. Three phosphonodipeptides containing ethyl 1-amino-2-phenylethylphosphonamidate were also prepared by converting phosphono monoacid into phosphonochloridate and reacting it with amino acid ester. Benzyl ethoxyphosphonyl-glycyl-glycine ethyl ester also was synthesized from ethyl glycylglycinate and ethyl benzylphosphonochloridate derived from direct chlorination of diethyl benzylphosphonate

  摘要 采用四种不同的偶联方法合成了四种含1-氨基烷基膦酸酯的膦酰二肽。然后将其中之一转化为单酸、乙基氢 1-(N-乙酰基-脯氨酰)氨基-2-苯基乙基膦酸酯。还通过将膦酰基单酸转化为膦酰氯并与氨基酸酯反应制备了含有1-氨基-2-苯基乙基膦酰胺酸乙酯的三种膦酰二肽。苄基乙氧基膦酰-甘氨酰-甘氨酸乙酯也由甘氨酰甘氨酸乙酯和苄基膦酰氯乙酯合成，由苄基膦酸二乙酯与磷酰氯直接氯化得到。
• Novel Coumarin-Containing Aminophosphonatesas Antitumor Agent: Synthesis, Cytotoxicity, DNA-Binding and Apoptosis Evaluation
  作者：Ya-Jun Li、Cai-Yi Wang、Man-Yi Ye、Gui-Yang Yao、Heng-Shan Wang

  DOI：10.3390/molecules200814791

  日期：——

  A series of novel coumarin-containing α-aminophosphonates were synthesized and evaluated for their antitumor activities against Human colorectal (HCT-116), human nasopharyngeal carcinoma (human KB) and human lung adenocarcinoma (MGC-803) cell lines in vitro. Compared with 7-hydroxy-4-methylcoumarin (4-MU), most of the derivatives showed an improved antitumor activity. Compound 8j (diethyl 1-(3-(4-methyl-2-oxo-2H-chromen-7-yloxy) propanamido)-1-phenylethyl-Phosphonate), with IC50 value of 8.68 μM against HCT-116 cell lines, was about 12 fold than that of unsubstituted parent compound. The mechanism investigation proved that 8c, 8d, 8f and 8j were achieved through the induction of cell apoptosis by G1 cell-cycle arrest. In addition, the further mechanisms of compound 8j-induced apoptosis in HCT-116 cells demonstrated that compound 8j induced the activations of caspase-9 and caspase-3 for causing cell apoptosis, and altered anti- and pro-apoptotic proteins. DNA-binding experiments suggested that some derivatives bind to DNA through intercalation. The results seem to imply the presence of an important synergistic effect between coumarin and aminophosphonate, which could contribute to the strong chelating properties of aminophosphonate moiety.

  合成了一系列含有香豆素结构的α-氨基膦酸酯类新化合物，并评估了它们对体外人结直肠癌（HCT-116）、人鼻咽癌（人KB）和人肺腺癌（MGC-803）细胞系的抗癌活性。与7-羟基-4-甲基香豆素（4-MU）相比，大多数衍生物显示出增强的抗癌活性。化合物8j（二乙基1-（3-（4-甲基-2-氧-2H-色烯-7-基氧）丙酰胺基）-1-苯乙基膦酸酯），对HCT-116细胞系的IC50值为8.68 μM，是其未取代母体化合物的约12倍。机制研究表明，8c、8d、8f和8j通过诱导G1期细胞周期阻滞来实现细胞凋亡。此外，进一步揭示了化合物8j诱导HCT-116细胞凋亡的机制，表明化合物8j通过激活caspase-9和caspase-3引起细胞凋亡，并改变抗凋亡和促凋亡蛋白。DNA结合实验表明，某些衍生物通过嵌插与DNA结合。结果似乎暗示了香豆素和氨基膦酸酯之间存在重要的协同效应，这可能有助于氨基膦酸酯部分的强螯合特性。
• Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates
  作者：P. P. Onys’ko、T. V. Kim、Yu. V. Rassukanaya、E. I. Kiseleva、A. D. Sinitsa

  DOI：10.1007/s11176-005-0007-6

  日期：2004.9

  Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N-C triad were revealed and applied in the synthesis of α-aminophosphonic acid derivatives.

  开发了合成方法以制备含有电子和立体多样的烷基取代基的苯并咪唑基磷酸酯衍生物，以及它们的质子化异构体。揭示了磷酸化C=N-C三元组中的质子转移规律，并应用于α-氨基磷酸衍生物的合成。