(3-三氟甲基苯基)-氨基甲酸叔丁酯 | 109134-07-8

• 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: (3-三氟甲基苯基)-氨基甲酸叔丁酯
• 英文名称: tert-butyl 3-(trifluoromethyl)phenylcarbamate
• 英文别名: tert-Butyl (3-(trifluoromethyl)phenyl)carbamate；tert-butyl N-[3-(trifluoromethyl)phenyl]carbamate
• CAS: 109134-07-8
• 化学式: C₁₂H₁₄F₃NO₂
• 分子量: 261.244
• InChiKey: PLLZDOLFXQKWQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(N-BOC-Amino)benzotrifluoride
Synonyms: tert-Butyl 3-(trifluoromethyl)phenylcarbamate

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3-(N-BOC-Amino)benzotrifluoride
CAS number: 109134-07-8

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

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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.
Store in closed vessels.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C12H14F3NO2
Molecular weight: 261.2

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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, nitrogen oxides, hydrogen fluoride.

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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

反应信息

• 作为反应物：
  描述：

  (3-三氟甲基苯基)-氨基甲酸叔丁酯 在 三乙烯二胺 、 三乙基硅烷 、 N-fluoro-2-naphthoylquininium tetrafluoroborate 、 仲丁基锂 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 various solvents 为溶剂， 生成 (3R)-3-(5-氯-2-甲氧基苯基)-3-氟-6-(三氟甲基)-1H-吲哚-2-酮
  参考文献：
  名称：

  使用金鸡纳生物碱（F-CA-BF4）的N-氟铵盐进行BMS-204352（MaxiPost）的对映选择性合成。

  摘要：

  描述了由金鸡纳生物碱的N-氟铵盐介导的强效Maxi-K钾通道开放剂（BMS-204352）的对映选择性合成。评价了两种合成途径。ee高达88％（单次重结晶后> 99％）。

  DOI：

  10.1039/b303113f
• 作为产物：
  描述：

  间氨基三氟甲苯 以89的产率得到(3-三氟甲基苯基)-氨基甲酸叔丁酯
  参考文献：
  名称：

  3-substituted oxindole derivatives as potassium channel modulators

  摘要：

  提供了一种新型的3-苯基氧吲哚衍生物，其化学式为##STR1##其中R为氢、羟基或氟；R1、R2、R3和R4各自独立地为氢、C.sub.1-4烷基、卤素、三氟甲基、苯基、对甲基苯基或对三氟甲基苯基；或R1和R2、R2和R3或R3和R4相互连接形成苯并环；R5为氢或C.sub.1-4烷基；R6为氯或三氟甲基；或其无毒的药学上可接受的盐、溶剂或水合物，它们是大电导钙激活钾通道的开放剂，并且在治疗对钾通道开放有反应的疾病方面有用。

  公开号：

  US05565483A1

文献信息

• Accessing Difluoromethylated and Trifluoromethylated <i>cis</i> ‐Cycloalkanes and Saturated Heterocycles: Preferential Hydrogen Addition to the Substitution Sites for Dearomatization
  作者：Xue Zhang、Liang Ling、Meiming Luo、Xiaoming Zeng

  DOI：10.1002/anie.201907457

  日期：2019.11.18

  Reported here is a straightforward process in which a cyclic (alkyl)(amino)carbene/Rh catalyst system facilitates the preferential addition of hydrogen to the substitution sites of difluoromethylated and trifluoromethylated arenes and heteroarenes, leading to dearomative reduction. This strategy enables the diastereoselective synthesis of cis-difluoromethylated and cis-trifluoromethylated cycloalkanes

  此处报道的是一种简单的方法，其中环状（烷基）（氨基）卡宾/ Rh催化剂体系有助于将氢优先添加到二氟甲基化和三氟甲基化的芳烃和杂芳烃的取代位上，从而导致脱芳族还原反应。该策略使非对映选择性合成顺式-二氟甲基化和顺式-三氟甲基化的环烷烃和饱和的杂环，甚至允许形成具有定义的赤道取向的二-和三氟甲基的全顺式多-三氟甲基化的环状产物。氘标记研究表明，氢优先攻击平面芳烃的取代位，从而导致脱芳香化作用，可能以异质Rh为反应性物种，
• Synthesis of3H and14C labeled (S)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-3-fluoro-6-(trifluoromethyl)-2H-indol-2-one, maxipost?. An agent for post-stroke neuroprotection
  作者：Douglas D. Dischino、Valentin K. Gribkoff、Piyasena Hewawasam、George M. Luke、J. Kent Rinehart、Tony L. Spears、John E. Starrett

  DOI：10.1002/jlcr.652

  日期：2003.2

  The syntheses of tritium labeled (S)-3-(5-chloro-2-[OC3H3]methoxyphenyl-1,3-dihydro-3-fluoro-6-(trifluoromethyl)-1H-indol-2-one, and carbon-14 (S)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-3-fluoro-6-(trifluoromethyl)-2H-[2,3-14C2] indol-2-one are reported. The 3H-labeled compound was prepared in a two-step synthesis from C3H3I. The final product was purified via chiral HPLC to yield the desired enantiomer in a 4% radiochemical yield and a specific activity of 60 Ci/mmol. The 14C-labeled compound was prepared in a four-step synthesis from diethyl [carboxylate-14C1,2] oxalate. The final product was purified via chiral HPLC to yield the desired enantiomer in a 20% radiochemical yield and a specific activity of 28.4 μCi/mg. Copyright © 2002 John Wiley & Sons, Ltd.

  报告了氚标记的(S)-3-(5-氯-2-[OC3H3]甲氧基苯基)-1,3-二氢-3-氟-6-(三氟甲基)-1H-吲哚-2-酮和碳-14标记的(S)-3-(5-氯-2-甲氧基苯基)-1,3-二氢-3-氟-6-(三氟甲基)-2H-[2,3-14C2]吲哚-2-酮的合成。3H标记的化合物是通过从C3H3I进行两步合成制备的。最终产物通过手性HPLC纯化，得到所需的对映体，放化产率为4%，比活度为60 Ci/mmol。14C标记的化合物是通过从二乙基[羧酸-14C1,2]草酸酯进行四步合成制备的。最终产物通过手性HPLC纯化，得到所需的对映体，放化产率为20%，比活度为28.4 μCi/mg。版权所有 © 2002 John Wiley & Sons, Ltd.
• Catalytic Enantioselective Fluorination of Oxindoles
  作者：Yoshitaka Hamashima、Toshiaki Suzuki、Hisashi Takano、Yuta Shimura、Mikiko Sodeoka

  DOI：10.1021/ja0513077

  日期：2005.7.1

  developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluorinated in a highly enantioselective manner (up to 96% ee). In addition, when R was a hydrogen atom, enantioselective fluorination followed by solvolysis gave

  我们开发了一种高效催化对映选择性氟化的羟吲哚衍生物。在催化量的手性 Pd 配合物 2 (2.5 mol%) 存在下，各种底物，包括芳基和烷基取代的羟吲哚，以高度对映选择性的方式（高达 96% ee）氟化。此外，当 R 是氢原子时，对映选择性氟化然后溶剂分解得到单氟化酯，ee 高达 93%。据我们所知，这是羟吲哚催化对映选择性氟化的第一个例子。
• Ligand-Promoted <i>Meta</i>-C–H Arylation of Anilines, Phenols, and Heterocycles
  作者：Peng Wang、Marcus E. Farmer、Xing Huo、Pankaj Jain、Peng-Xiang Shen、Mette Ishoey、James E. Bradner、Steven R. Wisniewski、Martin D. Eastgate、Jin-Quan Yu

  DOI：10.1021/jacs.6b04966

  日期：2016.7.27

  Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic

  在这里，我们报告了一种通用的 3-乙酰氨基-2-羟基吡啶类配体的开发，这些配体使用降冰片烯作为瞬态介质促进苯胺、杂环芳香胺、苯酚和 2-苄基杂环的间位 CH 芳基化。提供了 120 多个例子，证明了这种配体支架能够实现广泛的底物和偶联伙伴范围。使用该配体还首次实现了以杂环芳基碘化物作为偶联伙伴的间位 CH 芳基化。通过允许来那度胺衍生物的间位 CH 芳基化，展示了这种药物发现转化的效用。还展示了该反应的无银方案的第一步。
• Vanilloid receptor ligands and their use in treatments
  申请人：Bo Y. Yunxin

  公开号：US20060183745A1

  公开（公告）日：2006-08-17

  Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  具有一般结构的化合物及其组合物，用于治疗急性、炎症性和神经性疼痛、牙痛、普通头痛、偏头痛、集群头痛、混合血管和非血管综合征、紧张性头痛、一般炎症、关节炎、风湿病、骨关节炎、炎性肠道疾病、炎性眼部疾病、炎性或不稳定膀胱疾病、牛皮癣、伴有炎症成分的皮肤疾病、慢性炎症症状、炎症性疼痛及相关的过敏性疼痛和触痛、神经性疼痛及相关的过敏性疼痛和触痛、糖尿病性神经病痛、烧伤性神经痛、交感神经维持性疼痛、去神经综合征、哮喘、上皮组织损伤或功能障碍、单纯疱疹、呼吸、泌尿、消化或血管区域内脏运动障碍、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠道疾病、胃溃疡、十二指肠溃疡、腹泻、坏死性剂引起的胃病变、毛发生长、血管运动性或过敏性鼻炎、支气管疾病或膀胱疾病。