(4-CBZ-氨基苯基)三氟硼酸钾 | 850623-45-9

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟硼酸钾系列
• 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: (4-CBZ-氨基苯基)三氟硼酸钾
• 中文别名: 4-(苄氧基羰基氨基)苯基三氟硼酸钾
• 英文名称: 4-(benzyloxycarbonylamino)-phenyl trifluoroborate
• 英文别名: Potassium (4-cbz-aminophenyl)trifluoroborate；potassium;trifluoro-[4-(phenylmethoxycarbonylamino)phenyl]boranuide
• CAS: 850623-45-9
• 化学式: C₁₄H₁₂BF₃NO₂*K
• 分子量: 333.159
• InChiKey: ADBHDDIXRRMUNK-UHFFFAOYSA-N

物化性质

• 熔点：
  250-266℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P305+P351+P338,P405,P261,P280,P304+P340
• 危险性描述：
  H319,H315,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Potassium (4-Cbz-aminophenyl)trifluoroborate
Product Name:
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Potassium (4-Cbz-aminophenyl)trifluoroborate
Ingredient name:
CAS number: 850623-45-9

---

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:

---

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.

---

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.

---

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.

---

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.

---

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: C14H12BF3KNO2
Molecular weight: 333.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen fluoride.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (4-CBZ-氨基苯基)三氟硼酸钾 、 1-(4-喹啉基)甲胺 在 potassium carbonate 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以42%的产率得到benzyl N-[4-(6-oxocyclohexen-1-yl)phenyl]carbamate
  参考文献：
  名称：

  使用钯催化的三氟硼酸盐交叉偶联反应对环状 α-碘酮进行 α-芳基化和炔基化

  摘要：

  通过钯催化的环状 α-碘代烯酮与芳基三氟硼酸钾盐的交叉偶联反应，描述并说明了 α-芳基-和 α-炔基环己烯酮的快速合成。该程序可以轻松获得用电子给体和受体取代基官能化的 α-芳基化和炔基化环己烯酮，收率良好。

  DOI：

  10.1055/s-0029-1218580
• 作为产物：
  描述：

  C₁₆H₁₈BNO₄ 在 potassium hydrogen bifluoride 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (4-CBZ-氨基苯基)三氟硼酸钾
  参考文献：
  名称：

  (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones 通过 Suzuki-Miyaura 交叉偶联反应使用芳基三氟硼酸盐的功能化：方便的对映选择性制备 α-取代的 β-氨基酸

  摘要：

  Pd(OAc) 2 催化的 1-苯甲酰基-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones 与芳基三氟硼酸钾交叉偶联反应的简单方案已开发。该反应在 110 °C 下使用无配体催化剂进行。在所有情况下，观察到 1-苯甲酰基-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones 和芳基三氟硼酸盐完全转化为 CC 偶联产物在 30- 360 分钟 值得注意的是，芳基三氟硼酸钾中存在的多种基团（-CF 3 、-OMe、-SEt、-CN、-CHO、-Cl、-Cbz、-NCbz、-OH、-CO 2 H）可能是容忍。Suzuki-Miyaura 产品中的环内双键氢化，然后酸水解，得到高度对映体富集的 α-芳基取代的 β-氨基酸。

  DOI：

  10.1002/ejoc.201000852

文献信息

• Synthesis and trypanocidal activity of a library of 4-substituted 2-(1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ols
  作者：Michael N. Balfour、Caio H. Franco、Carolina B. Moraes、Lucio H. Freitas-Junior、Hélio A. Stefani

  DOI：10.1016/j.ejmech.2017.01.040

  日期：2017.3

  A library of 16 4-substituted 2-(1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ols 17–32 has been synthesized for use in biological testing against Trypanosoma cruzi, the protozoan parasite that causes Chagas disease. The 4-substituted 2-(1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ols 17–32 were subjected to biological testing to evaluate their efficacy against intracellular Trypanosoma cruzi (Y strain) amastigotes

  16 4-取代的2-（1的文库ħ吡咯并[3,2- c ^ ]吡啶-2-基）丙-2-醇17 - 32已被用于合成在抗生物测试克氏锥虫，原生动物寄生虫导致恰加斯病。四取代的2-（1 ħ吡咯并[3,2- c ^ ]吡啶-2-基）丙-2-醇17 - 32进行生物测试，以抗胞内评估其疗效克氏锥虫（Y株）以苯甲硝唑为参照化合物感染U2OS人细胞的变形虫。一式两份进行该测定（两个独立实验），并进行高含量分析（HCA）以测定锥虫活性。所测试的化合物的三呈现相对高的杀锥虫活性（19，22和29）中，观察到严重然而宿主细胞毒性伴随。将需要对高活性化合物进行化学优化并合成更多化合物以用于针对克鲁氏锥虫的生物学测试，以提高选择性，从而可以建立结构-活性关系，以提供对化学和生物学方面的更深入的分析。
• Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products
  作者：Emily C. Gentry、Lydia J. Rono、Martina E. Hale、Rei Matsuura、Robert R. Knowles

  DOI：10.1021/jacs.7b13616

  日期：2018.3.7

  noncovalent open-shell complexes can be intercepted by the stable nitroxyl radical TEMPO· to form alkoxyamine-substituted pyrroloindolines with high levels of enantioselectivity. Further elaboration of these optically enriched adducts can be achieved via a catalytic single-electron oxidation/mesolytic cleavage sequence to furnish transient carbocation intermediates that may be intercepted by a wide range

  尽管人们对自由基阳离子合成化学的兴趣不断增长，但控制这些中间体反应中的对映选择性仍然是一个挑战。基于对酶系统中色氨酸氧化的最新见解，我们报告了一种光催化方法，用于生成吲哚自由基阳离子作为与手性磷酸根阴离子的氢键加合物。这些非共价开壳络合物可以被稳定的硝酰自由基TEMPO·拦截，形成具有高水平对映选择性的烷氧基胺取代的吡咯并吲哚啉。这些光学富集的加合物的进一步精制可以通过催化单电子氧化/介晶裂解序列来实现，以提供可被多种亲核试剂拦截的瞬时碳阳离子中间体。总而言之，这个两步序列提供了一种简单的催化方法，可以通过标准实验方案从常见的合成中间体获得各种对映体富集形式的取代吡咯并吲哚啉。介绍了该方法的设计、开发、机理研究和范围，以及该方法在几种二聚吡咯并吲哚啉天然产物合成中的应用。
• Synthesis of a Tyr-Tyr Dipeptide Library and Evaluation Against Tumor Cells
  作者：Stanley N.S. Vasconcelos、Juliana M. Sciani、Nicole M. Lisboa、Helio A. Stefani

  DOI：10.2174/1573406414666180309153142

  日期：2018.10.3

  functionalization of these Tyr-Tyr dipeptides with Suzuki-Miyaura and Sonogashira crosscoupling reactions in good yields. Twelve different Tyr-Tyr dipeptides were investigated against three cell lines: HaCaT; Jurkat-E6; and A2058. RESULTS Some of the Tyr-Tyr dipeptides showed activity against Jurkat-E6 leukaemia cells at low concentration, decreasing their viability, but not against non-tumor HaCaT cells

  背景技术蛋白质和肽的结构成分，氨基酸已被用作合成具有更复杂分子的抗多种癌症的分子。目的正在寻找新的抗癌化合物，特别是对于那些侵袭性强，预后较差的癌症（例如白血病）。方法在这里，我们报告了一种通过声化学反应合成Tyr-Tyr二肽的方法，然后以良好的产率将这些Tyr-Tyr二肽与Suzuki-Miyaura和Sonogashira交叉偶联反应进行功能化。针对三种细胞系，研究了十二种不同的Tyr-Tyr二肽。Jurkat-E6; 和A2058。结果一些Tyr-Tyr二肽在低浓度下对Jurkat-E6白血病细胞具有活性，降低了它们的活力，但不是针对非肿瘤的HaCaT细胞，提示对肿瘤细胞具有特异性的细胞毒性。结论所有的二肽都能降低Jurkat细胞系的活力，但是A2058细胞系对肽的处理反应不好。一些修饰的Tyr-Tyr二肽对白血病肿瘤细胞表现出选择性活性。
• Highly efficient palladium-catalyzed Suzuki–Miyaura reactions of potassium aryltrifluoroborates with 5-iodo-1,3-dioxin-4-ones in water: an approach to α-aryl-β-ketoesters
  作者：Adriano S. Vieira、Rodrigo L.O.R. Cunha、Clécio F. Klitzke、Julio Zukerman-Schpector、Hélio A. Stefani

  DOI：10.1016/j.tet.2009.11.027

  日期：2010.1

  The high efficient palladium-catalyzed Suzuki-Miyaura reactions of potassium aryltrifluoroborates 3 with 5-iodo-1,3-dioxin-4-ones 2a-b in water as only solvent in the presence of n-Bu4NOH as base is reported. The respective 5-aryl-1,3-dioxin-4-ones 4a-n were obtained in good to excellent yields. The catalyst system provides high efficiency at low load using electronically diverse coupling partners. The obtained 2,2,6-trimethyl-5-aryl-1,3-dioxin-4-ones were transformed into corresponding alpha-aryl-beta-ketoesters 6 by reaction with an alcohol in the absence of solvent. (C) 2009 Elsevier Ltd. All rights reserved.
• Palladium(II)-Catalyzed Direct Arylation of Enaminones Using Organotrifluoroborates
  作者：Haibo Ge、Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/ja710221c

  日期：2008.3.1

  A Pd(II)-catalyzed reaction for the direct aryation of cyclic enaminones is reported. The reactivity of electron-rich, electron-poor, and sterically encumbered organotrifluoroborates was investigated. This reaction represents a unique use for organotrifluoroborates as coupling partners and discloses the utility of enaminones for direct-functionalization reactions. It provides immediate access to arylpiperidine, indolizidine, and quinolizidine scaffolds from the corresponding mono- and bicyclic, unattenuated enaminones.