4-(二乙基膦)丁酸 | 38694-48-3

• 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: 4-(二乙基膦)丁酸
• 英文名称: γ-diethoxyphosphorylbutyric acid
• 英文别名: 4-(diethoxyphosphinoyl)butanoic acid；4-(diethyloxyphosphoryl)butyric acid；4-(diethoxyphosphinyl)butanoic acid；4-(diethoxyphosphoryl)butanoic acid；4-(diethylphosphate)butyric acid；diethyl,4-phosphonobutyric acid；4-diethoxyphosphorylbutanoic acid
• CAS: 38694-48-3
• 化学式: C₈H₁₇O₅P
• mdl: MFCD00775370
• 分子量: 224.194
• InChiKey: LCHMQUIASGRBNV-UHFFFAOYSA-N

物化性质

• 熔点：
  62°C
• 沸点：
  140-145 °C(Press: 0.03 Torr)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36/37/39
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Diethylphosphonobutanoic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Diethylphosphonobutanoic acid
CAS number: 38694-48-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H17O5P
Molecular weight: 224.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(二乙基膦)丁酸 在 硼烷四氢呋喃络合物 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 diethyl (4-hydroxybutyl)phosphonate
  参考文献：
  名称：

  [EN] NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL ANTI-DIABETIC AGENTS
  [FR] NOUVEAUX AGENTS ANTIDIABÉTIQUES UTILES AVEC DES DÉRIVÉS DE BENZIMIDAZOLE CYCLIQUES

  摘要：

  结构式（I）的新化合物是AMP-蛋白激酶的激活剂，并且在治疗、预防和抑制由AMPK激活的蛋白激酶介导的疾病方面非常有用。本发明的化合物在治疗2型糖尿病、高血糖、代谢综合征、肥胖、高胆固醇血症和高血压方面非常有用。

  公开号：

  WO2010051206A1
• 作为产物：
  描述：

  4-膦酰丁酸三乙酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 4-(二乙基膦)丁酸
  参考文献：
  名称：

  磷霉素的双前药替代抗疟药和抗结核药。

  摘要：

  合成了一系列11种磷霉素替代物的双前药衍生物，并研究了它们抑制恶性疟原虫和结核分枝杆菌的体外生长的能力。将新戊酰氧基甲基（POM）膦酸酯前药修饰物与异羟肟酸酯部分的各种前药衍生化反应相结合。大多数化合物对恶性疟原虫的活性与磷霉素相近或逊于磷霉素。N-苄基取代的氨基甲酸酯前药6f是最具活性的抗疟疾类似物，IC50值为0.64 µM。与磷霉素和母体POM前药5相反，2-硝基呋喃和2-硝基噻吩前药6i和6j显示出有希望的抗结核活性。

  DOI：

  10.1016/j.bmcl.2019.03.009

文献信息

• Synthetic Fosmidomycin Analogues with Altered Chelating Moieties Do Not Inhibit 1-Deoxy-D-xylulose 5-phosphate Reductoisomerase or Plasmodium falciparum Growth In Vitro
  作者：René Chofor、Martijn Risseeuw、Jenny Pouyez、Chinchu Johny、Johan Wouters、Cynthia Dowd、Robin Couch、Serge Van Calenbergh

  DOI：10.3390/molecules19022571

  日期：——

  Fourteen new fosmidomycin analogues with altered metal chelating groups were prepared and evaluated for inhibition of E. coli Dxr, M. tuberculosis Dxr and the growth of P. falciparum K1 in human erythrocytes. None of the synthesized compounds showed activity against either enzyme or the Plasmodia. This study further underlines the importance of the hydroxamate functionality and illustrates that identifying effective alternative bidentate ligands for this target enzyme is challenging.

  制备了14种改变了金属配位基团的磷霉素类似物，并评估了它们对大肠杆菌Dxr、结核分枝杆菌Dxr的抑制作用以及在人类红细胞中对恶性疟原虫K1生长的抑制作用。合成的化合物均未显示对任一酶或疟原虫的活性。这项研究进一步强调了羟肟酸基团的重要性，并表明确定该靶酶的有效替代双齿配体具有挑战性。
• Pd-Catalyzed Highly Chemo- and Regioselective Hydrocarboxylation of Terminal Alkyl Olefins with Formic Acid
  作者：Wenlong Ren、Jianxiao Chu、Fei Sun、Yian Shi

  DOI：10.1021/acs.orglett.9b02101

  日期：2019.8.2

  An efficient Pd-catalyzed hydrocarboxylation of alkenes with HCOOH is described. A wide variety of linear carboxylic acids bearing various functional groups can be obtained with excellent chemo- and regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO.

  描述了用HCOOH有效地Pd催化的烯烃加氢羧化反应。在温和的反应条件下，可以得到具有优异的化学和区域选择性的各种带有各种官能团的线性羧酸。反应过程操作简单，不需要处理有毒的CO。
• Activation anionique du phosphite de diethyle par le fluorure de potassium depose sur alumine, synthese de phosphonates fonctionalises
  作者：Didier Villemin、Rassem Racha

  DOI：10.1016/s0040-4039(00)84375-0

  日期：1986.1

  Dry reactions of diethylphosphite on KF-Al2O3 with different. electrophiles conduct to the synthesis of functionalized phosphonates.

  亚磷酸二乙酯在KF-Al 2 O 3上的干反应有不同。亲电试剂可进行功能化膦酸酯的合成。
• 一种端位羧酸的合成方法
  申请人：常州大学

  公开号：CN110423191B

  公开（公告）日：2022-03-29

  本发明公开了一种端位羧酸的合成方法，其特征在于：在惰性气体的保护下，将式(3)所示的烯烃、甲酸、乙酸酐、Pd(OAc)2以及单磷配体TFPP按比例加入有机溶剂中，在80‑90℃条件下，式(3)所示的烯烃、甲酸和乙酸酐在金属钯盐Pd(OAc)2和单磷配体TFPP催化作用下经48‑72h的氢羰基化反应制得下式所示的端位羧酸，反应完成后分离目标产物端位羧酸；其中式(3)所示的烯烃选自环烯烃或R1为推电子基团的直链烯烃。采用本发明所述的方法能够在低温非高压的温和条件下反应得到对应的端位羧酸及其衍生物，且所述合成方法步骤简便、便于操作，产率高，能够大大的节约能源和提高合成效率。
• Synthesis of New Phosphonated Tripod Ligands as Putative New Therapeutic Agents in the Chelation Treatment of Metal Intoxications
  作者：Ramon Burgada、Theodorine Bailly、Marc Lecouvey、Valery Larue、Yves Leroux

  DOI：10.1002/1099-0690(200101)2001:2<349::aid-ejoc349>3.0.co;2-f

  日期：2001.1

  In a quest for new chelation therapy drugs for the treatment of intoxication by actinides, some new phosphonated chelating tripod ligands have been synthesized. They have been obtained by means of a coupling reaction between a diethylphosphonoalkanoic acid activated with N,N′-disuccinimidyl carbonate (DSC) and a series of polyamines, with subsequent deprotection of the phosphonate groups.

  为了寻找治疗锕系元素中毒的新螯合治疗药物，合成了一些新的膦化螯合三脚架配体。它们是通过用 N,N'-二琥珀酰亚胺碳酸酯 (DSC) 活化的二乙基膦酰基链烷酸和一系列多胺之间的偶联反应获得的，随后将膦酸酯基团脱保护。