2-氧代-4-苯丁基磷酸二甲酯 | 41162-19-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 2-氧代-4-苯丁基磷酸二甲酯
• 中文别名: 2-氧基-4-苯基丁基膦酸二甲酯
• 英文名称: dimethyl(2-oxo-4-phenylbutyl)phosphonate
• 英文别名: Dimethyl (2-oxo-4-phenylbutyl)phosphonate；1-dimethoxyphosphoryl-4-phenylbutan-2-one
• CAS: 41162-19-0
• 化学式: C₁₂H₁₇O₄P
• 分子量: 256.238
• InChiKey: ONYIBVIIOCEBIV-UHFFFAOYSA-N

物化性质

• 沸点：
  120-122 °C (0.5 mmHg)
• 密度：
  1.152±0.06 g/cm3(Predicted)
• 闪点：
  >110°C
• 溶解度：
  氯仿（微溶）、甲醇（微溶）
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

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：
  S24/25
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	Dimethyl (2-oxo-4-phenylbutyl)phosphonate tech. 85% Material Safety Data Sheet
Synonym:	None Known
CAS:	41162-19-0

Section 1 - Chemical Product MSDS Name:Dimethyl (2-oxo-4-phenylbutyl)phosphonate tech. 85% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
41162-19-0	Dimethyl (2-oxo-4-phenylbutyl)phosphon	85%	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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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:
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:
Wash thoroughly after handling. Use with adequate ventilation. 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 cool, dry place. 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# 41162-19-0: 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
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 120-122 deg C @ 0.5mmg
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: C12H17O4P
Molecular Weight: 256.0904

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
None reported.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Phosphine, carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 41162-19-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Dimethyl (2-oxo-4-phenylbutyl)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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 41162-19-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 41162-19-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 41162-19-0 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

制备方法与用途

用途

2-氧代-4-苯丁基磷酸二甲酯（比马前列素杂质12）是抗青光眼剂比马前列素的中间体。比马前列素是一种人工合成的前列腺素，与前列腺素F2α在结构上相关。

反应信息

• 作为反应物：
  描述：

  2-氧代-4-苯丁基磷酸二甲酯 在 Candida antarctica lipase B 、 lithium hydroxide monohydrate 、 potassium tert-butylate 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 甲基叔丁基醚 、 丙酮 为溶剂， 反应 16.75h， 生成 比马前列素
  参考文献：
  名称：

  A New Synthetic Approach to Prostaglandin Analogues: Synthesis of Bimatoprost via Lipase Enzymatic Catalysis

  摘要：

  报道了一种简单、便捷且高效的合成方法，通过脂肪酶介导的手性前体Corey内酯二醇作为底物进行立体选择性还原，合成(15S)比马前列素(4)。该方法采用斯温氧化、脂肪酶酶促还原和维蒂希反应作为关键步骤来合成比马前列素。与已报道的方法相比，这种方法具有较高的产率、成本效益，且简化了合成步骤。

  DOI：

  10.14233/ajchem.2017.20878
• 作为产物：
  描述：

  1-碘-4-苯基丁烷-2-酮 以60的产率得到2-氧代-4-苯丁基磷酸二甲酯
  参考文献：
  名称：

  Synth. Commun. 2012, 42, 1288-1305

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-氧代-4-苯丁基磷酸二甲酯 、 [(1S,2R,3R,4R)-4-benzoyloxy-3-formyl-2-[(Z)-7-oxo-7-propan-2-yloxyhept-2-enyl]cyclopentyl] benzoate 在 2-氧代-4-苯丁基磷酸二甲酯 作用下， 以65的产率得到[(1S,2R,3R,4R)-4-benzoyloxy-3-[(E)-3-oxo-5-phenylpent-1-enyl]-2-[(Z)-7-oxo-7-propan-2-yloxyhept-2-enyl]cyclopentyl] benzoate
  参考文献：
  名称：

  Synth. Commun. 2012, 42, 1288-1305

  摘要：

  DOI：

文献信息

• A Facile and Efficient Synthesis of (15R)-Latanoprost from Chiral Precursor Corey Lactone Diol
  作者：K VIJENDHAR、B SRINIVAS、SATHYANARAYANA BOODIDA

  DOI：10.1007/s12039-015-0963-2

  日期：2015.11

  synthetic protocol is a good alternative for the synthesis of latanoprost with high stereo selectivity and improved yield. A simple, convenient and convergent approach for the synthesis of (15R) latanoprost is reported with high stereo selectivity and improved yield from chiral precursor Corey lactone diol using Swern oxidation, allylic reduction and Wittig reaction conditions.

  开发了一种有效的不对称合成途径，用于在Swern氧化，烯丙基还原和Wittig反应条件下，以Corey内酯二醇为手性底物，合成抗青光眼剂（15R）-拉坦前列素。在该方法中，使用甲醇中的低成本催化剂NiCl 2 / NaBH 4一步即可完成酮基和烯烃官能团的还原。该新的合成方案是合成具有高立体选择性和提高收率的拉坦前列素的良好选择。 据报道，使用Swern氧化，烯丙基还原和Wittig反应条件，从手性前体Corey内酯二醇合成立体（15R）拉坦前列素具有简便，便捷和收敛的方法，其立体选择性高，产率提高。
• Process for the synthesis of prostaglandin derivatives
  申请人：Technopharma S.A.

  公开号：EP1721894A1

  公开（公告）日：2006-11-15

  An alternative method for the synthesis of prostaglandin F analogues, in particular, analogues of PGF2α and specifically for the synthesis of latano-prost, wherein the transformation of the lactone intermediate (5) into the corresponding lactol (7) is carried out by treating the lactone intermediate (5) with a silane, preferably polymethylhydrosiloxane (PMHS), in the presence of a titanocene - and preferably titanocene fluoride. The method enables considerable production economies with respect to the conventional reduction of lactone with diisobutylaluminum hydride (DIBAL-H).

  一种合成前列腺素F类似物的方法，特别是PGF2α类似物，特别是用于合成拉坦前列腺素，其中通过用硅烷处理乳内中间体(5)，优选使用聚甲基氢硅氧烷(PMHS)，在存在钛烯化合物，最好是钛烯氟化物的情况下，将乳内中间体(5)转化为相应的乳糖(7)。 该工艺与二异丁基氢化铝(DIBAL-H)还原内酯相比，可显著降低生产成本。
• Process for the preparation of latanoprost
  申请人：——

  公开号：US20030149294A1

  公开（公告）日：2003-08-07

  Disclosed is a novel process for the preparation of the anti-glaucoma drug Latanoprost, in good yield, in large amounts and with desired purity. Also disclosed are novel intermediates for the above process.

  揭示了一种新颖的制备抗青光眼药物拉唑前列素的方法，产量高，数量大且纯度良好。还披露了上述方法的新颖中间体。
• GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington’s Disease-Related Phenotypes
  作者：Congcong Wang、Yu-Fang Zhang、Shimeng Guo、Quan Zhao、Yanping Zeng、Zhicheng Xie、Xin Xie、Boxun Lu、Youhong Hu

  DOI：10.1021/acs.jmedchem.0c01133

  日期：2021.1.28

  studies showed that Comp-43 reduces mHTT levels by targeting GPR52 and promotes survival of mouse primary striatal neurons. Moreover, in vivo study showed that Comp-43 not only reduces mHTT levels but also rescues HD-related phenotypes in HdhQ140 mice. Taken together, our study confirms that inhibition of GPR52 is a promising strategy for HD therapy, and the GPR52 antagonist Comp-43 might serve as a lead

  GPR52是一种孤儿G蛋白偶联受体（GPCR），最近被认为是亨廷顿氏病（HD）（一种无法治愈的单基因神经退行性疾病）的潜在药物靶标。在这项研究中，我们发现GPR52的纹状体敲低可降低成年HdhQ140小鼠的mHTT水平，从而将GPR52确认为HD靶标。此外，通过结构-活性关系（SAR）研究，我们发现了一种高效且特异的GPR52拮抗剂Comp- 43，IC 50值为0.63μM 。进一步的研究表明，Comp- 43通过靶向GPR52降低mHTT水平，并促进了小鼠原代纹状体神经元的存活。此外，体内研究表明Comp- 43不仅降低了mHTT水平，而且还挽救了HdhQ140小鼠的HD相关表型。两者合计，我们的研究证实，抑制GPR52是HD治疗的一种有前途的策略，而GPR52拮抗剂Comp- 43可能充当进一步研究的先导化合物。
• A General Procedure for the Preparation of β-Ketophosphonates
  作者：Kevin M. Maloney、John Y. L. Chung

  DOI：10.1021/jo901552k

  日期：2009.10.2

  A mild, high-yielding procedure for the preparation of β-ketophosphonates is described. The condensation is general with respect to the ester and phosphonate, and the products are obtained in high yields within minutes at 0 °C. The reaction procedure is operationally simple and amenable to large-scale preparations.

  描述了制备β-酮膦酸酯的温和的高产率方法。对于酯和膦酸酯而言，缩合是普遍的，并且在0℃下在数分钟内以高收率获得产物。该反应程序操作简单并且适于大规模制备。