(3,3-二乙氧基丙基)磷酸二乙酯 | 15110-17-5

• 物质功能分类: 化学试剂 - 有机试剂 - 膦酸酯/膦酸盐
• 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: (3,3-二乙氧基丙基)磷酸二乙酯
• 英文名称: diethyl 3,3-diethoxypropylphosphonate
• 英文别名: diethoxy-3,3 propylphosphonate de diethyle；diethyl (3,3-diethoxypropyl)phosphonate；diethyl(3,3-diethoxypropyl)phosphonate；3--propionaldehyd-diaethylacetal；(3,3-Diaethoxy-propyl)-phosphonsaeure-diaethylester；3-Diaethoxyphosphono-propionaldehyd-diaethylacetal；3-diethoxyphosphoryl-1,1-diethoxypropane
• CAS: 15110-17-5
• 化学式: C₁₁H₂₅O₅P
• 分子量: 268.29
• InChiKey: WKPXMGJOGYEGNW-UHFFFAOYSA-N

物化性质

• 沸点：
  98-100 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37,S39
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090

SDS

Name:	Diethyl (3 3-Diethoxypropyl)Phosphonate Material Safety Data Sheet
Synonym:	None Known
CAS:	15110-17-5

Section 1 - Chemical Product MSDS Name:Diethyl (3 3-Diethoxypropyl)Phosphonate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15110-17-5	Diethyl (3,3-Diethoxypropyl)Phosphonat	95.0	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Do NOT use mouth-to-mouth resuscitation.
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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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# 15110-17-5: 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: Clear liquid
Color: yellow to brown - orange-yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 98-100 deg C@ 0.07mmHg
Freezing/Melting Point: Not available.
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: C11H25O5P
Molecular Weight: 268.1458

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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, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15110-17-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diethyl (3,3-Diethoxypropyl)Phosphonate - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 15110-17-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15110-17-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15110-17-5 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

反应信息

• 作为反应物：
  描述：

  (3,3-二乙氧基丙基)磷酸二乙酯 在 盐酸 、 正丁基锂 、 碳酸氢铵 作用下， 以 乙醇 为溶剂， 反应 23.0h， 生成 [2-(2,5-dioxo-imidazolidin-4-yl)-1-methyl-ethyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  制备和转化D'ω-甲酰基烷基膦酸酯使氨基羧基烷基膦酸酯酸化

  摘要：

  已经描述了通过酸水解由亚磷酸三乙酯和溴缩醛得到的相应缩醛的ω-甲酰基烷基膦酸酯。在氰化物和胺存在下的水溶液中，这些化合物会生成氨基腈（Strecker）或乙内酰脲（Bucherer）。这些反应提供了多种化合物，这些化合物通过酸水解（Strecker）或碱性然后酸水解（Bucherer）生成纯的氨基羧基烷基膦酸（膦酰丙氨酸等）。

  DOI：

  10.1016/s0040-4020(01)92454-8
• 作为产物：
  描述：

  3-氯丙醛二乙醇缩醛 、 sodium diethyl phosphite 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3,3-二乙氧基丙基)磷酸二乙酯
  参考文献：
  名称：

  Normant,H.; Sturtz,G., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1961, vol. 253, p. 2366 - 2368

  摘要：

  DOI：

文献信息

• Synthesis and characterization of novel phosphonocarboxylate inhibitors of RGGT
  作者：Fraser P. Coxon、Łukasz Joachimiak、Arafath Kaja Najumudeen、George Breen、Joanna Gmach、Christina Oetken-Lindholm、Rebecca Way、James E. Dunford、Daniel Abankwa、Katarzyna M. Błażewska

  DOI：10.1016/j.ejmech.2014.06.062

  日期：2014.9

  selective inhibitors of Rab geranylgeranyl transferase (RabGGTase, RGGT), an enzyme implicated in several diseases including ovarian, breast and skin cancer. Here we present the synthesis and biological characterization of an extended set of this class of compounds, including lipophilic derivatives of the known RGGT inhibitors. From this new panel of PCs, we have identified an inhibitor of RGGT that is

  抗骨质疏松药物双膦酸盐的膦酸羧酸盐 (PC) 类似物代表第一类 Rab 香叶基香叶基转移酶 (RabGGTase, RGGT) 选择性抑制剂，该酶与卵巢癌、乳腺癌和皮肤癌等多种疾病有关。在这里，我们介绍了一组扩展的此类化合物的合成和生物学表征，包括已知 RGGT 抑制剂的亲脂性衍生物。从这组新的 PC 中，我们鉴定了一种 RGGT 抑制剂，它与已发表的最活跃的膦酰基羧酸盐具有相似的效力，但与异戊二烯焦磷酸合酶相比，对这种酶具有更高的选择性。还提出了对结构要求的新见解，表明只有最有效的第三代双膦酸盐的 PC 类似物才能抑制 RGGT。此外，
• A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner–Wadsworth–Emmons reaction
  作者：Henryk Krawczyk、Katarzyna Wąsek、Jacek Kędzia、Jakub Wojciechowski、Wojciech M. Wolf

  DOI：10.1039/b712145h

  日期：——

  The synthesis of α-, β- and γ-substituted α-phosphono-γ-lactones was accomplished using different ring closure and ring homologation strategies. It was found that the lactones could be selectively transformed into the corresponding ethyl cyclopropanecarboxylates by treatment with sodium ethoxide in boiling THF. The reported reaction provides an attractive alternative to the classical homologous Horner–Wadsworth–Emmons approach to the construction of cyclopropanes with electron-withdrawing functionalities.

  通过不同的环闭合和环同系化策略，成功合成了α-、β-和γ-取代的α-磷酸-γ-内酯。研究发现，这些内酯可以通过在沸腾的四氢呋喃中用乙醇钠处理，选择性地转化为相应的乙基环丙烷羧酸酯。所报道的反应为构建带有吸电子功能的环丙烷提供了一种吸引人的替代方法，超越了经典的同系化Horner-Wadsworth-Emmons方法。
• [EN] COMPOUNDS FOR INHIBITING 1- DEOXY-D-XYLULOSE- 5 - PHOSPHATE REDUCTOISOMERASE<br/>[FR] COMPOSÉS DESTINÉS À INHIBER LA 1-DÉSOXY-D-XYLULOSE-5-PHOSPHATE RÉDUCTOISOMÉRASE
  申请人：UNIV GEORGE WASHINGTON

  公开号：WO2013006444A1

  公开（公告）日：2013-01-10

  [0082] In particular, the compound is effective to inhibit Dxr in Mycobacterium tuberculosis (Mtb). The present invention relates to compounds having general formula (I) or where X is an acidic group, such as carboxylate, phosphonate, sulfate, and tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, preferably 2, 3, or 4. The compounds inhibits l-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr), particularly Dxr in Mycobacterium tuberculosis (Mtb).

  特别是，该化合物能有效抑制结核分枝杆菌（Mtb）中的Dxr。本发明涉及具有通式（I）的化合物，其中X是酸性基团，如羧酸盐、膦酸盐、硫酸盐和四唑基；Ar是取代或未取代的芳香或杂环芳基团；n为0、1、2、3或4，优选为2、3或4。这些化合物抑制l-脱氧-D-木糖-5-磷酸还原异构酶（Dxr），特别是结核分枝杆菌（Mtb）中的Dxr。
• Compounds for inhibiting 1-deoxy-D-xylulose-5-phosphate reductoisomerase
  申请人：Boshoff Helena I.

  公开号：US09593136B2

  公开（公告）日：2017-03-14

  In particular, the compound is effective to inhibit Dxr in Mycobacterium tuberculosis (Mtb). The present invention relates to compounds having general formula (I) or (II) where X is an acidic group, such as carboxylate, phosphonate, sulfate, and tetrazole; Ar is a substituted or unsubstituted aromatic or heteroaromatic group; and n is 0, 1, 2, 3, or 4, preferably 2, 3, or 4. The compounds inhibits 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr), particularly Dxr in Mycobacterium tuberculosis (Mtb).

  特别是，该化合物能有效抑制结核分枝杆菌（Mtb）中的Dxr。本发明涉及具有一般式（I）或（II）的化合物 其中X是酸性基团，如羧酸盐、膦酸盐、硫酸盐和四唑基；Ar是取代或未取代的芳香或杂芳基团；n为0、1、2、3或4，优选为2、3或4。这些化合物抑制1-脱氧-D-木糖-5-磷酸还原异构酶（Dxr），特别是结核分枝杆菌（Mtb）中的Dxr。
• Design of potential bisubstrate inhibitors against Mycobacterium tuberculosis (Mtb) 1-deoxy-d-xylulose 5-phosphate reductoisomerase (Dxr)—evidence of a novel binding mode
  作者：Géraldine San Jose、Emily R. Jackson、Eugene Uh、Chinchu Johny、Amanda Haymond、Lindsay Lundberg、Chelsea Pinkham、Kylene Kehn-Hall、Helena I. Boshoff、Robin D. Couch、Cynthia S. Dowd

  DOI：10.1039/c3md00085k

  日期：——

  In most bacteria, the nonmevalonate pathway is used to synthesize isoprene units. Dxr, the second step in the pathway, catalyzes the NADPH-dependent reductive isomerization of 1-deoxy-D-xylulose-5-phosphate (DXP) to 2-C-methyl-D-erythritol-4-phosphate (MEP). Dxr is inhibited by natural products fosmidomycin and FR900098, which bind in the DXP binding site. These compounds, while potent inhibitors of Dxr, lack whole cell activity against Mycobacterium tuberculosis (Mtb) due to their polarity. Our goal was to use the Mtb Dxr-fosmidomycin co-crystal structure to design bisubstrate ligands to bind to both the DXP and NADPH sites. Such compounds would be expected to demonstrate improved whole cell activity due to increased lipophilicity. Two series of compounds were designed and synthesized. Compounds from both series inhibited Mtb Dxr. The most potent compound (8) has an IC50 of 17.8 μM. Analysis shows 8 binds to Mtb Dxr via a novel, non-bisubstrate mechanism. Further, the diethyl ester of 8 inhibits Mtb growth making this class of compounds interesting lead molecules in the search for new antitubercular agents.

  在大多数细菌中，非梅瓦隆酸途径用于合成异构烯单位。该途径的第二步是Dxr，它催化NADPH依赖的1-脱氧-D-木酮糖-5-磷酸（DXP）转化为2-C-甲基-D-赤藓糖-4-磷酸（MEP）的还原异构化反应。Dxr受到天然产品fosmidomycin和FR900098的抑制，这些化合物与DXP结合位点结合。这些化合物虽然是Dxr的强效抑制剂，但由于其极性，缺乏对结核分枝杆菌（Mtb）的全细胞活性。我们的目标是利用Mtb Dxr-fosmidomycin共晶结构设计双底物配体，以同时结合DXP和NADPH位点。这类化合物预计由于其增强的疏水性而表现出更好的全细胞活性。设计并合成了两系列化合物。两系列中的化合物均抑制Mtb Dxr。最强效的化合物（8）的IC50为17.8 µM。分析表明，化合物8通过一种新颖的非双底物机制与Mtb Dxr结合。此外，化合物8的二乙酯抑制了Mtb的生长，这使得这一类化合物成为寻找新抗结核药物的有趣领先分子。