(5-羧基戊基)三苯基溴化磷 | 50889-29-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (5-羧基戊基)三苯基溴化磷
• 中文别名: 5-羧戊基三苯基溴化膦；5-羧戊基三苯基溴化磷；5-羧基戊基-三苯基溴化磷；5-羧基戊基三苯基溴化磷
• 英文名称: (5-carboxypentyl)triphenylphosphonium bromide
• 英文别名: (5-carboxypentyl)triphenylphosphine bromide；6-Triphenylphosphonium bromide hexanoic acid；triphenyl-6-hexanoic acid phosphonium bromide；(5-carboxybutyl)triphenylphosphonium bromide；(5-carboxy-l-pentyl)triphenylphosphonium bromide；6-Triphenylphosphaniumylhexanoate;hydrobromide；6-triphenylphosphaniumylhexanoate;hydrobromide
• CAS: 50889-29-7
• 化学式: Br*C₂₄H₂₆O₂P
• 分子量: 457.347
• InChiKey: JUWYRPZTZSWLCY-UHFFFAOYSA-N

物化性质

• 熔点：
  197-201 °C
• 溶解度：
  易溶于氯仿和甲醇。
• 稳定性/保质期：
  如果按照规定使用和储存，则不会分解，也未有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22,R36/37/38
• WGK Germany：
  3
• 安全说明：
  S22,S26,S36,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器保持密封，并储存在阴凉、干燥的地方。同时，确保工作环境具有良好的通风或排气设施。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
(5-Carboxypentyl)(triphenyl)phosphonium bromide
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
(5-Carboxypentyl)(triphenyl)phosphonium bromide
Ingredient name:
CAS number: 50889-29-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C24H26O2P.Br
Molecular weight: 457.3

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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, hydrogen bromide.

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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

制备方法与用途

用途

5-羧基戊基-三苯基溴化磷可用作医药中间体、催化剂和歧化剂等。

反应信息

• 作为反应物：
  描述：

  (5-羧基戊基)三苯基溴化磷 在 氯化亚砜 、 potassium tert-butylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 (Z)-辣椒素
  参考文献：
  名称：

  A facile procedure for synthesis of capsaicin

  摘要：

  DOI：

  10.1021/jo00275a040
• 作为产物：
  描述：

  6-溴己酸 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 17.0h， 以100%的产率得到(5-羧基戊基)三苯基溴化磷
  参考文献：
  名称：

  细胞色素P450 CYP505X对辣椒素的脂肪羟基化和环氧化作用

  摘要：

  微生物细胞色素P450酶（CYP）能够模拟人CYP的代谢。一项挑战是鉴定相应的药物代谢物，并将底物特异性与人类酶的底物特异性进行比较。在这项研究中，来自烟曲霉的VIII类自足CYP （CYP505X）及其酶的变体在大肠杆菌中异源表达。使用活性药物成分（API）和（杂环）化合物确定变体的底物范围。辣椒素（辣椒中的活性化合物）在全细胞介导的生物转化中被最有效地氧化（4.36μM/ min）。分离，纯化产物，并通过1D和2D NMR阐明其结构。这两种主要代谢物在亲脂性侧链上显示出修饰。具体地，将辣椒素在8位羟基化以得到（E） -8-羟基-N-（4-羟基-3-甲氧基苄基）-8-甲基非-6-烯酰胺并在双键上环氧化以得到N-（4-羟基-3-甲氧基苄基）-5-（3-异丙基环氧乙烷-2-基）-戊酰胺。

  DOI：

  10.1016/j.tet.2018.08.049
• 作为试剂：
  描述：

  (5-羧基戊基)三苯基溴化磷 、 (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol 在 (5-羧基戊基)三苯基溴化磷 作用下， 生成 7-[2-(4,4-Difluoro-3-hydroxyoctyl)-5-hydroxy-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoic acid
  参考文献：
  名称：

  Promotion of wound-healing with 15-keto-prostaglandin compounds

  摘要：

  一种促进伤口愈合的方法，包括向需要此类治疗的受试者施用15-酮前列腺素化合物的愈合有效量。

  公开号：

  US05252605A1

文献信息

• Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enones to Chiral Cycloalkanols with Three Contiguous Stereocenters
  作者：Yun-Ting Liu、Ji-Qiang Chen、Lin-Ping Li、Xin-Yang Shao、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1021/acs.orglett.7b01343

  日期：2017.6.16

  A highly efficient iridium-catalyzed asymmetric hydrogenation of tetrasubstituted cyclic enones has been developed for the enantioselective synthesis of chiral cycloalkanols with three contiguous stereocenters. The C═O and C═C bonds of the enone substrates were hydrogenated sequentially in one pot with excellent enantioselectivity (92 to >99% ee) and diastereoselectivity (dr 95:5 to >99:1). The reaction

  已经开发了一种高效的铱催化的四取代环烯酮的不对称氢化反应，用于对映体选择性合成具有三个连续立体中心的手性环烷醇。烯酮底物的C═O和C═C键在一锅中依次氢化，具有优异的对映选择性（92至> 99％ee）和非对映选择性（dr 95：5至> 99：1）。该反应为抗溃疡药罗沙前列醇的所有立体异构体提供了一种实用的方法。
• 1,2 diarylbenzimdazoles and their pharmaceutical use
  申请人：Schering AG

  公开号：US20020006948A1

  公开（公告）日：2002-01-17

  Benzimidazoles of general formula I 1 and the use of benzimidazole derivatives for the production of pharmaceutical agents for treatment and prophylaxis of diseases that are associated with a microglia activation are described.

  通用公式I的苯并咪唑及其衍生物的使用用于生产与微胶质细胞活化相关的疾病的药物制剂，用于治疗和预防这些疾病。
• Selective Functionalization of Antimycin A Through an <i>N</i>-Transacylation Reaction
  作者：Arnaud Chevalier、Yanmin Zhang、Omar M. Khdour、Sidney M. Hecht

  DOI：10.1021/acs.orglett.6b00882

  日期：2016.5.20

  proceeds through a bis-N-acylated intermediate, which undergoes facile deformylation. This transacylation reaction has been employed for the site-specific functionalization of the mitochondrial poison antimycin A, affording several novel derivatives. The selective cytotoxicity of some of these derivatives toward cultured A549 human lung epithelial adenocarcinoma cells, in comparison with WI-38 normal human

  3-（N-甲酰基氨基）水杨酸的酰化导致转酰基化而甲酰基部分丢失。反应通过双-N-酰化的中间体进行，该中间体进行容易的去甲酰基化。该转酰化反应已用于线粒体毒物抗霉素A的位点特异性功能化，提供了几种新型衍生物。与WI-38正常人肺成纤维细胞相比，这些衍生物中的一些对培养的A549人肺上皮腺癌细胞的选择性细胞毒性说明了这种转酰化反应的一种应用。
• Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations
  作者：Pantelia、Daskalaki、Cuquerella、Rotas、Miranda、Vougioukalakis

  DOI：10.3390/molecules24213957

  日期：——

  strong chemiluminescence performance are of high importance. We herein report the synthesis and chemiluminescence properties of eight novel phosphonium-functionalized amino-acylated luminol and isoluminol derivatives, designed as mitochondriotropic chemiluminescence reactive oxygen species trackers. Three different phosphonium cationic moieties were employed (phenyl, p-tolyl, and cyclohexyl), as well as

  活细胞中活性氧的监测提供了有关细胞功能和性能的宝贵信息。近年来，由于化学发光具有快速测量和高灵敏度等优点，基于化学发光的活性氧监测的发展受到越来越多的关注。在这方面，具有强化学发光性能的特定细胞器靶向跟踪器非常重要。我们在此报告了八种新型鏻功能化氨基酰化鲁米诺和异鲁米诺衍生物的合成和化学发光特性，这些衍生物被设计为线粒体化学发光活性氧类跟踪器。使用了三种不同的鏻阳离子部分（苯基、对甲苯基和环己基），以及两个烷酰基链（己酰基和十一酰基）作为桥接/连接体。合成是通过相应的邻苯二甲酰亚胺（作为邻苯二甲酰肼的前体）酰化，然后进行肼解来完成的。选择这种方法是因为（异）鲁米诺的直接酰化令人沮丧。评估了新衍生物的化学发光，并与母体分子的化学发光进行了比较。观察到所有衍生物的化学发光性能相对较差，以异鲁米诺为基础的化学发光性能最差。这一结果主要归因于化学发光氧化反应过程中荧光物种形成的产率低。选择这种方法
• Synthesis, biological evaluation, and structure activity relationship (SAR) study of pyrrolidine amide derivatives as <i>N</i>-acylethanolamine acid amidase (NAAA) inhibitors
  作者：Pan Zhou、Lei Xiang、Dongsheng Zhao、Jie Ren、Yan Qiu、Yuhang Li

  DOI：10.1039/c8md00432c

  日期：——

  N-Acylethanolamine acid amidase (NAAA) is one of the key enzymes involved in the degradation of fatty acid ethanolamides (FAEs), especially for palmitoylethanolamide (PEA). Pharmacological blockage of NAAA restores PEA levels, providing therapeutic benefits in the management of inflammation and pain. In the current work, we showed the structure-activity relationship (SAR) studies for pyrrolidine amide

  N-酰基乙醇胺酸酰胺酶（NAAA）是参与脂肪酸乙醇酰胺（FAE）降解的关键酶之一，尤其是对于棕榈酰乙醇酰胺（PEA）而言。NAAA的药理学阻断作用可恢复PEA水平，从而在炎症和疼痛的治疗中提供治疗益处。在当前的工作中，我们显示了吡咯烷酰胺衍生物作为NAAA抑制剂的结构-活性关系（SAR）研究。检查了吡咯烷酰胺的末端苯基的一系列芳族取代基或取代基。SAR数据表明，较小的亲脂性3-苯基取代基对于最佳效用是优选的。构象柔性的接头增加了吡咯烷酰胺衍生物的抑制能力，但降低了其对脂肪酸酰胺水解酶（FAAH）的选择性。构象上受限的接头没有增强抑制剂对NAAA的效力，但是改善了对FAAH的选择性。开发了几种低微摩尔有效的NAAA抑制剂，其中包括带有刚性4-苯基肉桂酰基的4g。透析和动力学分析表明4g通过竞争和可逆的机制抑制NAAA。此外，4g在脂多糖（LPS）诱导的急性肺损伤（ALI）模型中显示出较高的抗