1,4,8,11-四(氨甲酰基甲基)-1,4,8,11-四氮杂环十四烷 | 345612-63-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1,4,8,11-四(氨甲酰基甲基)-1,4,8,11-四氮杂环十四烷
• 中文别名: 1,4,8,11-四(氨基羰基甲基)-1,4,8,11-四氮杂环十四烷
• 英文名称: 1,4,8,11-tetrakis(carbamoylmethyl)-1,4,8,11-tetraazacyclotetradecane
• 英文别名: 1,4,8,11-Tetrakis(aminocarbonylmethyl)-1,4,8,11-tetraazacyclotetradecane；2-[4,8,11-tris(2-amino-2-oxoethyl)-1,4,8,11-tetrazacyclotetradec-1-yl]acetamide
• CAS: 345612-63-7
• 化学式: C₁₈H₃₆N₈O₄
• 分子量: 428.535
• InChiKey: IELGXFGSUVHRIY-UHFFFAOYSA-N

物化性质

• 沸点：
  762.0±60.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  避免氧化和水分

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  185
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 海关编码：
  2933990090
• 储存条件：
  保存方法：密封于阴凉、通风的干燥处。

SDS

---

Section 1: Product Identification
Chemical Name: 1,4,8,11-Tetraazacyclotetradecane-N,N',N",N'''-tetraacetamide, min. 98%
CAS Registry Number: 345612-63-7
Formula: C18H36N8O4
EINECS Number: none
Chemical Family: organic amine
Synonym: 2-(4,8,11-Tris-carbamoylmethyl-1,4,8,11tetraaza-cyclotetradec-1-yl)-acetamide

---

Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 345612-63-7 100% no data no data

---

Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract
Primary Routes of Exposure: Inhalation, skin, eyes
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes irritation to the skin
Inhalation: Causes irritation to the nose, mucous membranes and respiratory tract
Ingestion: No information on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract
Chronic Health Affects: No information available on long-term chronic effects
NTP: No
IARC: No
OSHA: No

---

SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

---

SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: no data
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry chemical or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire, this material may emit irritating organic fumes
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards

---

SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non-combustible adsorbent and
Spill and Leak Procedures:
swept up.

---

SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container. Keep in a cool, dry place.

---

SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

---

SECTION 9: Physical and Chemical Properties
Color and Form: white to yellow powder
Molecular Weight: 428.53
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: insoluble

---

SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: oxidizing agents
Decomposition Products: carbon dioxide, carbon monoxide, nitrogen oxides and organic fumes

---

SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files
Carcinogenic Effects: No data
Mutagenic Effects: No data
Tetratogenic Effects: No data

---

SECTION 12: Ecological Information
Ecological Information: No information available

---

SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations

---

SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

---

SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Title compound not listed
Second Ingredient: none

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  lead(II) perchlorate trihydrate 、 1,4,8,11-四(氨甲酰基甲基)-1,4,8,11-四氮杂环十四烷 以 水 为溶剂， 以86%的产率得到[Pb(TETAM)](ClO₄)₂*2.8H₂O
  参考文献：
  名称：

  Cyclam衍生物的合成，表征和X射线晶体结构。8.八齿氨基甲酰基武装大环对铅（II）螯合的热力学和动力学评估。

  摘要：

  在开发包含铅选择性螯合剂的杂化有机-无机萃取材料及其在水净化过程中的应用的过程中，三种N-氨基甲酰基甲基取代的1,4,8,11-四氮杂环十四烷（环酰胺）的铅（II）结合特性）已通过光谱法（IR，UV-vis，MALDI-TOF MS，（1）H和（13）C NMR），X射线晶体学，电位法和动力学方法进行了充分研究。溶液NMR研究表明，Pb（2+）离子被截留在由四个大环氮和四个酰胺氧原子组成的分子笼中。在水溶液中测定的质子化和铅结合常数显示出线性依赖性，因此所有三种衍生物在任何pH值下均具有相似的亲和力。热力学和动力学参数揭示了分子内氢键也发挥了关键作用，四乙酰胺衍生物L（1）的晶体结构也证明了这一点，该结构涉及每个大环叔胺的孤对和一个属于附加臂的酰胺氢原子。与L（1）相比，对于N-（二甲基）氨基甲酰基甲基-和N-（二乙基）氨基甲酰基甲基取代的cyclams（分别为L（2）和L（3）），没有这

  DOI：

  10.1021/ic0508019
• 作为产物：
  描述：

  在 disodium hydrogenphosphate 、 3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt 、 potassium carbonate 、 sodium chloride 作用下， 生成 1,4,8,11-四(氨甲酰基甲基)-1,4,8,11-四氮杂环十四烷
  参考文献：
  名称：

  The NiCEST Approach: Nickel(II) ParaCEST MRI Contrast Agents

  摘要：

  Paramagnetic Ni(II) complexes are shown here to form paraCEST MRI contrast agents (paraCEST = paramagnetic: chemical exchange saturation transfer; NICEST = Ni(II) based CEST agents). Three azamacro-cycles with amide pendent groups bind Ni(II) to form stable NiCEST contrast agents including 1,4,7-tris-(carbamoylmethyl)-1,4,7-triazacyclononane. (L1), 1,4,8,11-tetrakis(carbamoylmethyl)-1,4,8,11-tetraazacyclo-tetradecane (L2), and 7,13-bis(carbamoylmethyl)-1,4,10-trioxa-7,13-diazacyclopentadecane (L3). [Ni(L3)](2+), [Ni(L1)](2+), and [Ni(L2)](2+) have CEST peaks attributed to amide protons that are shifted 72, 76, and 76 ppm from the bulk water resonance, respectively. Both CEST MR images and CEST spectroscopy show that [Ni(L3)](2+) has the largest CEST effect in 100 mM NaCl, 20 mM HEPES pH 7.4 at 37 degrees C. This larger CEST effect is attributed to the sharper proton resonances of the complex which arise from a rigid structure and low relaxivity.

  DOI：

  10.1021/ja307909x

文献信息

• [EN] MACROCYCLES, COBALT AND IRON COMPLEXES OF SAME, AND METHODS OF MAKING AND USING SAME<br/>[FR] MACROCYCLES, COMPLEXES DE COBALT ET DE FER DE CEUX-CI, ET PROCÉDÉS DE PRÉPARATION ET D'UTILISATION CORRESPONDANTS
  申请人：RES FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK UNIVERSITY AT BUFFALO

  公开号：WO2015038943A1

  公开（公告）日：2015-03-19

  Provided are macrocyclic compounds and iron or cobalt coordinated macrocyclic compounds. The compounds can be used as MRI contrast agents. Certain compounds are redox active and can be used to assess the biological redox status of a sample.

  提供的是大环化合物和铁或钴配位的大环化合物。这些化合物可以用作磁共振成像对比剂。某些化合物具有氧化还原活性，可用于评估样品的生物氧化还原状态。
• Lead(II) complexes with amide-appended tetraazamacrocyclic ligands – Synthesis, structure, characterization and calculation studies
  作者：Krzysztof Lyczko、Monika Lyczko、Marek Pruszyński

  DOI：10.1016/j.poly.2020.114822

  日期：2020.12

  B3LYP/LANL2DZ,6-31G(d,p) calculations. The dimeric [Pb(TRITAM)]24+ (3a) and monomeric [Pb(TRITAM)]2+ (3b) complexes were obtained by reactions of lead(II) triflate and perchlorate with TRITAM. For the other ligands, the monomeric cationic complexes were only obtained. The total coordination number of the lead(II) ion is nine in 3a and eight in the remaining compounds. The coordination polyhedrons around the

  摘要五个新的铅（II）配合物[Pb（DOTAM）]（OTf）2（1a），[Pb（TETAM）]（OTf）2·2H2O（2a），[Pb（TETAM）]（ClO4）2·具有酰胺附加的四氮杂大环配体的2.8H 2 O（2b），[Pb（TRITAM）] 2（OTf）4（3a），[Pb（TRITAM）]（ ）2·nH2O（3b，n = 2.3或2.4）}在结构，光谱和热重分析方面进行了合成和表征。晶体结构基于单晶X射线衍射解析，并与通过DFT B3LYP / LANL2DZ，6-31G（d，p）计算获得的分子几何结构进行比较。通过三氟甲磺酸铅（II）和高氯酸盐与TRITAM反应获得二聚体[Pb（TRITAM）] 24+（3a）和单体[Pb（TRITAM）] 2+（3b）配合物。对于其他配体，仅获得单体阳离子配合物。铅（II）离子的总配位数为3a中的9个，其余化合物中为8个。金属中心周围的配位
• CoCEST: cobalt(ii) amide-appended paraCEST MRI contrast agents
  作者：Sarina J. Dorazio、Abiola O. Olatunde、Joseph A. Spernyak、Janet R. Morrow

  DOI：10.1039/c3cc45000g

  日期：——

  The first examples of air-stable CoII paraCEST MRI contrast agents are reported. Amide NH protons on the complexes give rise to CEST peaks that are shifted up to 112 ppm from the bulk water resonance. One complex has multiple CEST peaks that may be useful for ratiometric mapping of pH.

  本研究首次报道了空气稳定 CoII paraCEST MRI 造影剂的实例。络合物上的酰胺 NH 质子产生了 CEST 峰，这些峰与大量水共振相比偏移达 112 ppm。其中一种复合物具有多个 CEST 峰，可用于绘制 pH 比值图。
• Six, Seven or Eight Coordinate Fe^II, Co^IIor Ni^IIComplexes of Amide-Appended Tetraazamacrocycles for ParaCEST Thermometry
  作者：Abiola O. Olatunde、Christopher J. Bond、Sarina J. Dorazio、Jordan M. Cox、Jason B. Benedict、Michael D. Daddario、Joseph A. Spernyak、Janet R. Morrow

  DOI：10.1002/chem.201503125

  日期：2015.12.7

  complexes have a six‐coordinate metal ion bound to the 1‐, 4‐amide oxygen atoms and four nitrogen atoms of the tetraazamacrocycle. The [Fe(L2)]2+ complex has an unusual eight‐coordinate FeII bound to four amide oxygen atoms and four macrocyclic nitrogen atoms. For [Co(L2)]2+, one structure has seven‐coordinate CoII with three bound amide pendents and a second structure has a six‐coordinate CoII with two

  两个四氮杂大环的 Fe II 、Co II和 Ni II配合物（1,4,8,11-四（氨基甲酰基甲基）-1,4,8,11-四氮杂环十四烷（ L1 ）和 1,4,7,10-四（氨基甲酰基甲基） )‐1,4,7,10-四氮杂环十二烷 ( L2 ) 有望作为 paraCEST 试剂用于温度记录（paraCEST=顺磁化学交换饱和转移）。L1的Fe II 、Co II和 Ni II配合物显示出多达四个 CEST。峰偏移 ≤112 ppm，而L2的类似配合物仅在 ≤69 ppm 处显示单个 CEST 峰 [Co( L2 )] 2+ 、 [Fe( L2 ) 的 CEST 峰的温度系数 ( C T ) 比较。 ] 2+ 、[Ni( L1 )] 2+和 [Co( L1 )] 2+显示 [Co( L1 )] 2+的 CEST 峰在 4.7 处给出最大的C T (-0.66 ppm o C -1 ) T) 的
• Isomeric Co(<scp>ii</scp>) paraCEST agents as pH responsive MRI probes
  作者：Christopher J. Bond、Roy Cineus、Alexander Y. Nazarenko、Joseph A. Spernyak、Janet R. Morrow

  DOI：10.1039/c9dt04558a

  日期：——

  newly discovered isomer of Co(ii) (1,4,8,11-tetrakis(carbamoylmethyl)-1,4,8,11-tetraazacyclotetradecane = CCRM) produces four highly paramagnetically shifted chemical exchange saturation transfer (CEST) peaks. The 1,8-pendants of the complex are bound in a trans-arrangement to produce a Co(ii) complex of increased kinetic inertness. The isomers have a stabilized Co(ii) center (E1/2 of 540 to 550 mV

  一种新发现的Co（ii）异构体（1,4,8,11-四（氨基甲酰基甲基）-1,4,8,11-四氮杂环十四烷= CCRM）产生四个高度顺磁位移的化学交换饱和转移（CEST）峰。该复合物的1，8-链垂体以反式排列结合以产生动力学惰性增加的Co（ii）复合物。异构体具有稳定的Co（ii）中心（相对于SHE，E1 / 2为540至550 mV的E1 / 2）。1,8和1,4-异构体都是溶液中和组织匀浆中优异的pH探针，这是由于它们具有高度顺磁性位移的酰胺质子。这些异构体既产生比例pH读数，也产生与pH相关的酰胺质子交换速率常数。