1-苄基-1,4,8,11-四氮环十四烷 | 132723-93-4

• 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: 1-苄基-1,4,8,11-四氮环十四烷
• 中文别名: 1-苄基-1,4,8,11-四氮杂环十四烷
• 英文名称: 1-Benzyl-1,4,8,11-tetraazacyclotetradecane
• 英文别名: 1.benzyl-1,4,8,11-tetraazacyclotetradecane；N-benzylcyclam；benzylcyclam；Bz-cyclam；1-benzyl-1,4,8,11-tetrazacyclotetradecane
• CAS: 132723-93-4
• 化学式: C₁₇H₃₀N₄
• mdl: MFCD09263311
• 分子量: 290.452
• InChiKey: WNEKVKFZHNGHEH-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，不存在已知的危险反应。避免与氧化物、水分等接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.647
• 拓扑面积：
  39.3
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 储存条件：
  请将贮藏器密封保存，并将其存放在阴凉干燥处。同时，确保工作环境具备良好的通风或排气设施。

SDS

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Section 1: Product Identification
Chemical Name: N-Benzyl-1,4,8,11-tetraazacyclotetradecane, min. 98%
CAS Registry Number: 132723-93-4
Formula: C17H30N4
EINECS Number: none
Chemical Family: organic amine
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 132723-93-4 100% no data no data

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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

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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.

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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

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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.

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

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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.

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SECTION 9: Physical and Chemical Properties
Color and Form: white to yellow powder
Molecular Weight: 290.45
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: insoluble

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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

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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

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SECTION 12: Ecological Information
Ecological Information: No information available

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

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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

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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-苄基-1,4,8,11-四氮环十四烷 在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、150.0 kPa 条件下， 反应 186.0h， 生成
  参考文献：
  名称：

  具有 N-丙酸悬臂的铜 (II) Cyclam 配合物

  摘要：

  具有不同数量的 N-取代丙酸基团的四个环烷烃（1,4,8,11-四氮杂环十四烷）配体导致采用反式 I 构型（4+1 几何）的五配位铜 (II) 配合物，即配合物具有明显的菱形畸变的基态。从结构数据（X射线衍射分析和电子顺磁共振、UV/Vis和IR光谱）来看，随着丙酸基团取代的大环仲胺基团数量的增加，从方锥体到三角双锥体的畸变增加，这预计会导致相对较低的复杂稳定性。超氧化物歧化酶 (SOD) 和人血清激发实验的体外研究以及 64Cu 标记复合物的生物分布数据证实了这一点。

  DOI：

  10.1002/ejic.201500510
• 作为产物：
  描述：

  1,4,8,11-四氮杂环十四烷 在 盐酸 、 六甲基磷酰三胺 、 sodium hydroxide 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 1-苄基-1,4,8,11-四氮环十四烷
  参考文献：
  名称：

  Filali, Ayoub; Yaouanc, Jean-Jacques; Handel, Henri, Angewandte Chemie, 1991, vol. 103, # 5, p. 563 - 564

  摘要：

  DOI：

文献信息

• Mono N-functionalization of cyclic and linear tetraamines via their tridentate tricarbonylchromium complexes
  作者：Jean-Jacques Yaouanc、Nathalie Le Bris、Guénaëlle Le Gall、Jean-Claude Clément、Henri Handel、Hervé des Abbayes

  DOI：10.1039/c39910000206

  日期：——

  11-tetraazacyclotetradecane 2, 1,4,7,10-tetraazadecane 3 and 1,5,8,12-tetraazadodecane 4 have been selectively alkylated in high yield at the uncomplexed nitrogen atom, giving rise to mono N-functionalized tetraamines and bis-macrocyclic compounds.

  的FAC -LCR（CO）3个1,4,7,10-四的三齿配合物1，1,4,8,11-四氮杂2，1,4,7,10- tetraazadecane 3和1,5,8，已在未络合的氮原子上高产率地选择性地烷基化了十二-十四氮十二烷4，产生了单N-官能化的四胺和双大环化合物。
• A convenient method for the preparation of mono N-alkylated cyclams and cyclens in high yields
  作者：Cong Li、Wing-Tak Wong

  DOI：10.1016/s0040-4039(02)00497-5

  日期：2002.4

  Selective and high yield synthesis of mono N-substituted derivatives of cyclam and cyclen can be achieved by using a direct and general synthetic method with very mild reaction conditions.

  可以通过使用直接且通用的合成方法，在非常温和的反应条件下，选择性地高收率合成cyclam和cycln的单N-取代衍生物。
• An organic template approach for the synthesis of selectively functionalised tetraazacycloalkanes
  作者：Frédéric Boschetti、Franck Denat、Enrique Espinosa、Roger Guilard

  DOI：10.1039/b108244b

  日期：2002.2.12

  Selectively functionalised tetraazacycloalkanes are obtained from the open-chain tetraamine by using a bisaminal moiety acting both as a template agent and as a N-protecting group.

  选择性功能化的四氮杂环烷烃是通过使用一个双醛基团，从开放链四胺中获得的，该双醛基团既充当模板剂，又作为氮保护基团。
• General route for the synthesis of mono N-alkylated derivatives of tetraazamacrocycles
  作者：H. Bernard、J.J. Yaouanc、J.C. Clément、H. des Abbayes、H. Handel

  DOI：10.1016/s0040-4039(00)74848-9

  日期：1991.1

  The selective synthesis of mono N-substituted derivatives of tetraazamacrocycles can be achieved using a new boron triprotection easily removed after alkylation.

  可以使用在烷基化后容易除去的新型硼三保护来实现四氮杂大环的单N-取代的衍生物的选择性合成。
• Structure and Dynamics of Metallomacrocycles:  Recognition of Zinc Xylyl-Bicyclam by an HIV Coreceptor
  作者：Xiangyang Liang、John A. Parkinson、Michael Weishäupl、Robert O. Gould、Stephen J. Paisey、Hye-seo Park、Tina M. Hunter、Claudia A. Blindauer、Simon Parsons、Peter J. Sadler

  DOI：10.1021/ja0260723

  日期：2002.8.1

  Consideration of the anti-HIV activity of xylyl-bicyclam complexes of other metal ions suggests that affinity for carboxylates, configurational flexibility, and kinetic factors may all play roles in receptor recognition. For example, Pd(II) cyclam complexes interact only weakly with axial ligands and are inflexible and inactive, whereas Co(III) cyclams bind carboxylates strongly, are configurationally

  作为用于设计基于金属的治疗和诊断剂的平台，大环足够坚固以提供强大的金属结合位点和立体选择性定向官能团，但又足够灵活以适应生物靶标的诱导匹配识别所需的结构变化。我们考虑了共同受体 CXCR4（一种被 HIV 用于膜融合和细胞进入的 G 蛋白偶联受体）识别双-四氮杂大环二甲苯基-bicyclam（一种有效的抗 HIV 药物）的 Zn(II) 复合物。NMR 研究表明，Zn(II)(2)-二甲苯基-双环烷高氯酸盐的大环以两种主要构型存在于水溶液中，trans-I（氮手性 R,S,R,S）和 trans-III（S, S，R，R）。乙酸盐的加入引起了重大的结构变化。X 射线晶体学表明，醋酸盐复合物含有不寻常的顺式 V 环链烷烃构型（R、R、R、R 和折叠），醋酸盐与 Zn(II) 的双齿配位加上第二配位球之间的双H对角线 NH 质子位于相反的 cyclam 表面和乙酸酯羧酸氧。详细的 1D 和 2D