N-BOC4-氟-2-甲酰基苯胺 | 844891-31-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 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: N-BOC4-氟-2-甲酰基苯胺
• 中文别名: N-BOC4-氟-2-甲酰苯胺
• 英文名称: tert-butyl N-(2-formyl-4-fluorophenyl)carbamate
• 英文别名: tert-butyl N-(4-fluoro-2-formylphenyl)carbamate；tert-butyl (4-fluoro-2-formylphenyl)carbamate
• CAS: 844891-31-2
• 化学式: C₁₂H₁₄FNO₃
• mdl: MFCD07776962
• 分子量: 239.246
• InChiKey: KRTNPYAOWNCJNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  288.0±30.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-BOC 4-fluoro-2-formylaniline
Synonyms: tert-Butyl 4-fluoro-2-formylphenylcarbamate; 2-(Boc-Amino)-5-fluorobenzaldehyde

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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: N-BOC 4-fluoro-2-formylaniline
CAS number: 844891-31-2

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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: C12H14FNO3
Molecular weight: 239.2

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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：

  N-BOC4-氟-2-甲酰基苯胺 在 正丁基锂 、 potassium tert-butylate 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 叔丁醇 、 正戊烷 为溶剂， 反应 5.25h， 生成 5-fluoro-1-(triisopropylsilyl)-1H-indole
  参考文献：
  名称：

  寻求简单性和灵活性：合理获取 12 种氟代吲哚羧酸

  摘要：

  所有十二个在苯并环上带有氟取代基和羧基的吲哚羧酸已经被制备出来。直接来自相应的氟吲哚或氯化衍生物。通过氢/金属置换（“金属化”），或通过卤素/金属置换从溴或碘氟吲哚中提取，有机金属中间体每次都被二氧化碳捕获。在大多数情况下，尽管不是所有情况，五元环中的氮原子必须由三烷基甲硅烷基保护。一些溴或碘氟吲哚成功地经受了重卤素的碱性梯度驱动的选择性迁移。在通往目标化合物的途中意外发现。是 5-氟-N-（三烷基甲硅烷基）吲哚的严格位点选择性金属化（4-位的独家去质子化）。氟吲哚虽然以前是已知的，但可以使用 Bartoli 或 Leimgruber-Batcho 方法从适当取代的硝基苯中更方便地获得。精心设计了一种新的非常有吸引力的吲哚合成，包括 N-酰基保护的苯胺的邻位锂化，然后是邻位甲酰化、Wittig 氯亚甲基化和碱催化环化，并伴有脱氯化氢。这五个连续的步骤可以简化为一个方便的一锅协议。[在 SciFinder

  DOI：

  10.1002/ejoc.200600118
• 作为产物：
  描述：

  4-氟-2-羟甲基苯胺 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-BOC4-氟-2-甲酰基苯胺
  参考文献：
  名称：

  2-氨基苯甲醛与乙炔基二羧酸二烷基酯之间的膦催化反应：1,2-二氢喹啉衍生物的合成及烯烃化反应的发展

  摘要：

  通过使2-氨基苯甲醛衍生物和乙炔二羧酸二烷基酯与催化量的膦反应，可以很好地合成一系列1,2-二氢喹啉。该反应通过使用苯基硅烷的选择性原位氧化膦还原而被催化。此外，在相同的起始原料和还原剂的附加作用下，发现了新的烯烃化反应。氢/氘（H / D）交换实验揭示了该反应的可能机理。

  DOI：

  10.1021/acs.orglett.8b01870

文献信息

• [EN] DIAMIDE MACROCYCLES AS FACTOR XIA INHIBITORS<br/>[FR] MACROCYCLES DIAMIDES UTILISÉS EN TANT QU'INHIBITEURS DU FACTEUR XIA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016205482A1

  公开（公告）日：2016-12-22

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective factor XIa inhibitors or dual inhibitors of FXIa and plasma kallikrein. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.

  本发明提供了式(I)的化合物：或其立体异构体、互变异构体或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性因子XIa抑制剂或FXIa和血浆激肽酶的双重抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用它们治疗血栓栓塞和/或炎症性疾病的方法。
• Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives
  作者：Jiping Hao、Yi Xu、Zhongliang Xu、Zhiqiang Zhang、Weibo Yang

  DOI：10.1021/acs.orglett.8b03440

  日期：2018.12.21

  A Pd-catalyzed, highly regioselective and stereoselective three-component domino allylic substitution/N–H carbene insertion reaction under mild conditions is described. This reaction demonstrates a wide substrate scope and satisfactory functional group tolerance, providing a broad range of allylic sulfone-containing amino acid derivatives. Moreover, DBU mediates highly diastereoselective cross-dehydrogenative

  描述了在温和条件下Pd催化的，高度区域选择性和立体选择性的三组分多米诺烯丙基烯丙基取代/ NH卡宾插入反应。该反应证明了广泛的底物范围和令人满意的官能团耐受性，提供了范围广泛的含烯丙基砜的氨基酸衍生物。此外，DBU不使用过氧化物或任何金属氧化剂即可介导烯丙基砜的高度非对映选择性的交叉脱氢偶联环合反应。此开发的协议提供了7元环杂环化合物，其中既包含含砜的氨基酸酯，又包含一个季碳中心。机理研究表明，在这种环状结构中发生了异常的甘氨酸转运蛋白。
• Synthesis of regiospecifically substituted quinolines from anilines
  作者：Giorgio Chelucci、Ilaria Manca、Gerard A. Pinna

  DOI：10.1016/j.tetlet.2004.12.020

  日期：2005.1

  A protocol for the synthesis of quinolines substituted on both pyridine and benzo-fused rings is reported. The method is based on the formylation of a substituted N-(tert-butoxycarbonyl)aniline followed by direct cyclisation and aromatisation of the intermediate product obtained by condensation of the formed N-Boc o-aminobenzaldehyde with an enolisable carbonyl compound. Yields up to 88% have been

  报道了合成在吡啶和苯并稠合的环上取代的喹啉的方案。该方法是基于取代的甲酰化ñ - （叔丁氧羰基）苯胺，接着通过所形成的缩合获得的环化直接和中间产物的芳构化Ñ -Boc ö -aminobenzaldehyde与烯醇化羰基的化合物。已获得高达88％的产率。
• Stereodivergent Access to [6.7]-Fused <i>N</i>-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations
  作者：Zhan-Cai Ma、Lin-Wen Wei、Yuan Huang

  DOI：10.1021/acs.orglett.3c00269

  日期：2023.3.17

  seven-membered cyclic N-sulfonyl aldimines for the synthesis of a wide array of N-heterocycles with 1,3-nonadjacent stereogenic centers via palladium catalysis. The polarity of solvents was found to play a key role in the switch of diastereoselectivity. Furthermore, good enantioselectivities of these reactions were achieved by the employment of commercially available Wingphos as the chiral ligand.

  我们描述了乙烯基苯并恶嗪酮和七元环状N-磺酰醛亚胺的高效立体发散 [4 + 2] 环化反应，用于通过钯催化合成各种具有 1,3-不相邻立体中心的N-杂环。发现溶剂的极性在非对映选择性的转换中起着关键作用。此外，这些反应的良好对映选择性是通过使用市售的 Wingphos 作为手性配体实现的。
• Efficient synthesis of 3‐sulfonyl‐1,2‐dihydroquinolines via tandem <scp>aza‐Michael</scp> addition/cyclizations of <i>N</i>‐acyl‐protected 2‐aminobenzaldehyde with vinyl sulfones
  作者：Kai‐Kai Wang、Guo‐Yan Liu、Yan‐Li Li、Wen‐Wen Zhou、Jun‐Wei Ye、Yan‐Zhi Jia、Rongxiang Chen、Zhan‐Yong Wang

  DOI：10.1002/jhet.4729

  日期：2023.11

  A mild and effective method for the synthesis of 3-sulfonyl-1,2-dihydroquinolines from N-acyl-protected 2-aminobenzaldehyde with vinyl sulfones has been established. This reaction could rapidly proceed and exhibit different reactivity when employed the vinyl sulfones as nucleophile on aza-Michael addition/cyclization reaction, allow for the production of 1,2-DHQs in high yields up to 95%. In addition

  建立了一种温和有效的由N-酰基保护的2-氨基苯甲醛与乙烯基砜合成3-磺酰基-1,2-二氢喹啉的方法。当使用乙烯基砜作为氮杂迈克尔加成/环化反应的亲核试剂时，该反应可以快速进行并表现出不同的反应活性，从而可以以高达 95% 的高收率生产 1,2-DHQ。此外，通过X射线单晶结构分析证实了产物的化学结构。