(±)N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) | 176763-62-5

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机铋、钴、镨、钆、镓、铱、铼、钇、铽等
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II)
• 英文别名: (±)-Co(Sal^t-Bu,t-Bu)；(±)-Co(6,6'-(cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene)bis(2,4-di-tert-butylphenol))；Co(salen)；[(N,N'-bis(3,5-di-tert-butylsalicylidene)1,2-cyclohexanediaminato(2-))cobalt(II)]；rac-trans-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane diaminocobalt(II)；(R,R)-(-)-N,N'-Bis(3,5-ditert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II)；cobalt(2+);2,4-ditert-butyl-6-[[(1R,2R)-2-[(3,5-ditert-butyl-2-oxidophenyl)methylideneamino]cyclohexyl]iminomethyl]phenolate
• CAS: 176763-62-5
• 化学式: C₃₆H₅₂CoN₂O₂
• 分子量: 603.814
• InChiKey: ZFWPDJKMASHRPT-GAQUOPITSA-L

物化性质

• 熔点：
  >350 °C(lit.)
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  29349990
• 危险性防范说明：
  P280
• 危险性描述：
  H302+H312+H332
• 储存条件：
  保存方法：存于密闭、阴凉、干燥处。

SDS

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Section 1: Product Identification
Chemical Name: (1R,2R)-(-)-1,2-Cyclohexanediamino-N,N'-bis(3,5-di-t-butylsalicylidene)cobalt (II)
CAS Registry Number: 176763-62-5
Formula: C36H52CoN2O2
EINECS Number: none
Chemical Family: organometallic complexes
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 176763-62-5 100% 0.02mg/m3 (as Co) no data

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Section 3: Hazards Identification
Causes irritation of eyes, skin, and respiratory tract. May cause lung disease, polycythemia, congestive failure,
Emergency Overview:
and enlargement of the thyroid. Limited evidence of a carcinogenic effect.
Primary Routes of Exposure: Skin and eyes, ingestion and dust inhalation.
Eye Contact: Causes irritation, redness, and pain.
Skin Contact: May cause dermatitis. Causes irritation to skin. Symptoms include redness, itching, and pain.
Causes irritation to the respiratory tract. Symptoms may include coughing, shortness of breath, nausea,
Inhalation:
respiratory hypersensitivity, asthma.
Causes abdominal pain, nausea, vomiting, flushing of the face and ears, mild hypo tension, rash, and ringing
Ingestion:
in the ears.
Irritating to skin, eyes and respiratory tract. Causes abdominal pain, nausea, vomiting, coughing, and
Acute Health Affects:
shortness of breath.
Repeated oral administration of cobalt salts may reduce thyroid activity, cause blood disease, and damage
Chronic Health Affects: kidney, heart and lungs. Prolonged or repeated skin exposure may cause dermatitis. Limited evidence of a
carcinogenic effect.
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: not applicable
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, foam or dry powder
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 toxic 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 away from heat and direct sunlight.

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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: Material may form a fine dust. If possible, 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: Material may form a fine dust. If possible, 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: red-brown pwdr.
Molecular Weight: 603.76
Melting Point: 406-412°C
Boiling Point: no data
Vapor Pressure: not applicable
Specific Gravity: no data
Odor: none
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, organic fumes, and cobalt oxide.

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: Possible carcinogen
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: See category N096 for reporting.
Second Ingredient: None

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (±)N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 在 氢氟酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Enantioselective Radiosynthesis of Positron Emission Tomography (PET) Tracers Containing [¹⁸F]Fluorohydrins

  摘要：

  Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [F-18](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [F-18]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

  DOI：

  10.1021/ja5025645
• 作为试剂：
  描述：

  4-硝基苯乙烯 、 N-ethyl-N-fluorobenzenesulfonamide 在 (±)N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 作用下， 以 乙酸乙酯 为溶剂， 反应 10.0h， 以57%的产率得到N-ethyl-N-(2-fluoro-2-(4-nitrophenyl)ethyl)benzenesulfonamide
  参考文献：
  名称：

  钴催化发散氨基氟化和苯乙烯与N-氟磺酰胺的氨基化反应

  摘要：

  已经开发了苯乙烯与N-氟磺酰胺同时用作胺化剂和氟化剂的钴催化的氨基氟化反应。通过加入1.0当量的PPh 3，可以容易地实现从氨基氟化到氨化的催化反应中选择性的转换。两种转化在温和的反应条件下均能耐受多种底物。

  DOI：

  10.1021/acs.orglett.1c01308

文献信息

• Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes
  作者：Jeishla L. M. Matos、Suhelen Vásquez-Céspedes、Jieyu Gu、Takuya Oguma、Ryan A. Shenvi

  DOI：10.1021/jacs.8b11699

  日期：2018.12.12

  Herein we report the reductive coupling of electronically unbiased olefins with imines and aldehydes. Iron catalysis allows addition of alkyl-substituted olefins into imines through the intermediacy of free radicals, whereas a combination of catalytic Co(Sal t-Bu, t-Bu) and chromium salts enables a branch-selective coupling of olefins and aldehydes through the formation of a putative alkyl chromium intermediate

  使用金属氢化物氢原子转移 (MHAT) 催化将烯烃和有能力的亲自由基亲电子试剂偶联起来，可以轻松发生自由基加氢官能化。传统的双电子亲电子试剂一直不反应。在此，我们报告了电子无偏烯烃与亚胺和醛的还原偶联。铁催化允许通过自由基的中介将烷基取代的烯烃加成到亚胺中，而催化 Co(Sal t-Bu, t-Bu) 和铬盐的组合使烯烃和醛通过形成支链选择性偶联成为可能一种假定的烷基铬中间体。
• 一种治疗细菌感染的化合物
  申请人：苏州信诺维医药科技有限公司

  公开号：CN111303144B

  公开（公告）日：2020-11-27

  本发明公开了通式(I)所示的化合物或其药学上可接受的盐及其用于治疗细菌感染的用途。
• Asymmetric Catalytic Synthesis of α-Aryloxy Alcohols: Kinetic Resolution of Terminal Epoxides via Highly Enantioselective Ring-Opening with Phenols
  作者：Joseph M. Ready、Eric N. Jacobsen

  DOI：10.1021/ja9910917

  日期：1999.6.1

  terminal epoxides with catalyst 3b4 (Scheme 1, Nu ) OH) suggested that (salen)Co(III) complexes might also serve as effective catalysts for the enantioselective addition of phenols to epoxides. This strategy has proven successful, and we report here the first examples of kinetic resolution of epoxides with phenols, with the isolation of 1-aryloxy 2-alcohols (1) in high ee’s and yields. Reaction of 2.2

  哈佛大学化学与化学生物学系，剑桥，马萨诸塞州 02138 接收日期：1999 年 4 月 6 日 对映纯的 R-芳氧基醇 (1) 是不对称合成的重要目标，因为它们在多种药学上重要的化合物中作为关键合成中间体。 1 原则上，可以通过多种途径获得这些结构单元，包括芳氧基酮的不对称还原 2 或对映纯末端环氧化物与酚类的开环。其中，后者可能是最通用和最直接的，但将酚类加成到环氧化物中的可用方法极其有限。尚未设计出用于末端环氧化物的酚类开环的催化方法，3 且未催化反应需要强制条件，例如在酚盐存在下在极性溶剂中加热环氧化物至高温。这些热方法通常产量低，特别不适合敏感基材。因此，尽管最近发现了获得高光学纯度末端环氧化物的通用方法 4，但通过环氧化物与酚类开环来开发对映纯 R-芳氧基醇的路线仍然是一个未解决的问题。外消旋形式的末端环氧化物的易接近性使得末端环氧化物与酚的动力学拆分成为一种潜在的有吸引力的途径
• Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation
  作者：Sophia L. Shevick、Carla Obradors、Ryan A. Shenvi

  DOI：10.1021/jacs.8b06458

  日期：2018.9.26

  mechanistic model of this reaction through the use of reaction progress kinetic analysis (RPKA), radical clock experiments, and stoichiometric studies. Through exclusion of competing hypotheses, we conclude that the reaction proceeds through an unprecedented alkylcobalt to nickel direct transmetalation. Demonstration of catalytic alkene prefunctionalization, via spectroscopic observation of an organocobalt

  钴/镍双催化末端烯烃与碘芳烃的加氢芳基化利用容易获得的起始材料构建了复杂性，并且高度优先选择马尔可夫尼科夫（支化）产物。在这里，我们通过使用反应进程动力学分析（RPKA）、自由基时钟实验和化学计量研究，提出了该反应的机理模型。通过排除竞争假设，我们得出结论，该反应通过前所未有的烷基钴到镍的直接金属转移进行。通过有机钴物质的光谱观察，催化烯烃预官能化的演示将这种 Csp2-Csp3 交叉偶联方法与传统的金属转移过程（采用化学计量的有机金属亲核试剂）和有机卤化物跨镍的双金属氧化加成区别开来，描述为自由基断裂和随后的烷基自由基在第二个镍中心捕获。对反应的深入理解导致了优化的加氢芳基化程序，排除了外源氧化剂，证明金属转移是净氧化还原中性的。钴催化烯烃预官能化以及通过直接金属转移与镍催化循环的接触提供了一个新平台，以预备有用的方式融合这两个丰富的化学领域。
• Enantioselective Radiosynthesis of Positron Emission Tomography (PET) Tracers Containing [¹⁸F]Fluorohydrins
  作者：Thomas J. A. Graham、R. Frederick Lambert、Karl Ploessl、Hank F. Kung、Abigail G. Doyle

  DOI：10.1021/ja5025645

  日期：2014.4.9

  Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [F-18](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [F-18]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.