N-环己基-N-甲基-2-溴苯甲酰胺 | 349395-89-7

• 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-环己基-N-甲基-2-溴苯甲酰胺
• 中文别名: 2-溴-n-环己基-n-甲基苯甲酰胺
• 英文名称: 2-bromo-N-cyclohexyl-N-methylbenzamide
• CAS: 349395-89-7
• 化学式: C₁₄H₁₈BrNO
• mdl: MFCD01211895
• 分子量: 296.207
• InChiKey: PDEAYYAQSYOTJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: N-Cyclohexyl-N-methyl 2-bromobenzamide
Synonyms: 2-Bromo-N-cyclohexyl-N-methylbenzamide

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: N-Cyclohexyl-N-methyl 2-bromobenzamide
CAS number: 349395-89-7

---

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.

---

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.
Store in closed vessels.
Storage:

---

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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C14H18BrNO
Molecular weight: 296.2

---

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 bromide.

---

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：

  N-环己基-N-甲基-2-溴苯甲酰胺 在 氢氧化钾 、 硼烷四氢呋喃络合物 作用下， 生成 N-(2-bromobenzyl)-N-methylcyclohexylamine
  参考文献：
  名称：

  在钯催化的不对称烯丙基烷基化反应中，带有氮原子的手性亚砜配体是可立体控制的配位元素[1]

  摘要：

  通过使用带有氮原子的手性亚砜配体作为配位元素，例如手性α-亚磺酰基乙酰胺，β或γ-氨基亚砜和β-亚磺酰基磺酰胺，研究了钯催化的不对称烯丙基烷基化反应。证明了手性亚磺酰基功能对不对称诱导的影响。（S）-2-吡咯烷基苯基对甲苯基亚砜或（S）-2-（N-丁基-N-甲基氨基甲基）苯基对亚砜的用途甲苯催化的不对称烯丙基烷基化反应中的甲苯基亚砜作为手性配体，在我们研究的手性亚砜配体中提供了最高的对映选择性（分别为50％或58％ee）。亚砜基参与这些催化的不对称反应是合理的，并基于获得的立体化学结果提出了不对称诱导的机理。

  DOI：

  10.1016/s0957-4166(98)00394-2
• 作为产物：
  描述：

  N-甲基环己胺 、 2-溴苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到N-环己基-N-甲基-2-溴苯甲酰胺
  参考文献：
  名称：

  在钯催化的不对称烯丙基烷基化反应中，带有氮原子的手性亚砜配体是可立体控制的配位元素[1]

  摘要：

  通过使用带有氮原子的手性亚砜配体作为配位元素，例如手性α-亚磺酰基乙酰胺，β或γ-氨基亚砜和β-亚磺酰基磺酰胺，研究了钯催化的不对称烯丙基烷基化反应。证明了手性亚磺酰基功能对不对称诱导的影响。（S）-2-吡咯烷基苯基对甲苯基亚砜或（S）-2-（N-丁基-N-甲基氨基甲基）苯基对亚砜的用途甲苯催化的不对称烯丙基烷基化反应中的甲苯基亚砜作为手性配体，在我们研究的手性亚砜配体中提供了最高的对映选择性（分别为50％或58％ee）。亚砜基参与这些催化的不对称反应是合理的，并基于获得的立体化学结果提出了不对称诱导的机理。

  DOI：

  10.1016/s0957-4166(98)00394-2

文献信息

• Investigation of the Mechanism of C(sp³)−H Bond Cleavage in Pd(0)-Catalyzed Intramolecular Alkane Arylation Adjacent to Amides and Sulfonamides
  作者：Sophie Rousseaux、Serge I. Gorelsky、Benjamin K. W. Chung、Keith Fagnou

  DOI：10.1021/ja103081n

  日期：2010.8.11

  reactivity of C(sp(3))-H bonds adjacent to a nitrogen atom can be tuned to allow intramolecular alkane arylation under Pd(0) catalysis. Diminishing the Lewis basicity of the nitrogen lone pair is crucial for this catalytic activity. A range of N-methylamides and sulfonamides react exclusively at primary C(sp(3))-H bonds to afford the products of alkane arylation in good yields. The isolation of a Pd(II) reaction

  可以调整与氮原子相邻的 C(sp(3))-H 键的反应性，以允许在 Pd(0) 催化下进行分子内烷烃芳基化。降低氮孤对的路易斯碱度对于这种催化活性至关重要。一系列 N-甲基酰胺和磺酰胺仅在初级 C(sp(3))-H 键上反应，以高产率提供烷烃芳基化产物。Pd(II) 反应中间体的分离使得能够评估反应机理，重点是碱在 C(sp(3))-H 键断裂步骤中的作用。这些化学计量研究的结果，连同动力学同位素效应实验，为协调的金属化-去质子化 (CMD) 过渡态提供了罕见的实验支持，此前已在烷烃 C(sp(3))-H 芳基化中提出了这种过渡态。而且，DFT 计算揭示了新戊酸盐添加剂作为磷化氢从 Pd(II) 中间体解离的促进剂的额外作用，使 CMD 过渡态成为可能。最后，进行了动力学研究，揭示了反应速率表达及其与新戊酸盐浓度的关系。
• Steric Effect of Carboxylate Ligands on Pd-Catalyzed Intramolecular C(sp² )-H and C(sp³ )-H Arylation Reactions
  作者：Yutaka Tanji、Naoya Mitsutake、Tetsuaki Fujihara、Yasushi Tsuji

  DOI：10.1002/anie.201804566

  日期：2018.8.6

  carboxylic acid bearing three cyclohexylmethyl substituents at the α‐position, namely, tri(cyclohexylmethyl)acetic acid, is demonstrated to act as an efficient ligand source in Pd‐catalyzed intramolecular C(sp2)−H and C(sp3)−H arylation reactions. The reactions proceed smoothly under mild reaction conditions, even at room temperature due to the steric bulk of the carboxylate ligands, which accelerates the

  在α-位置带有三个环己基甲基取代基的大分子羧酸，即三（环己基甲基）乙酸被证明是Pd催化的分子内C（sp 2）-H和C（sp 3）的有效配体来源-H芳基化反应。由于羧酸盐配体的空间体积较大，即使在室温下，反应也可在温和的反应条件下顺利进行，这加快了催化循环中确定C H键活化步骤的速度。
• Photocatalysis in Aqueous Micellar Media Enables Divergent C–H Arylation and <i>N</i>-Dealkylation of Benzamides
  作者：Martyna Cybularczyk-Cecotka、Jędrzej Predygier、Stefano Crespi、Joanna Szczepanik、Maciej Giedyk

  DOI：10.1021/acscatal.2c00468

  日期：2022.3.18

  Photocatalysis in aqueous micellar media has recently opened wide avenues to activate strong carbon–halide bonds. So far, however, it has mainly explored strongly reducing conditions, restricting the available chemical space to radical or anionic reactivity. Here, we demonstrate a controllable, photocatalytic strategy that channels the reaction of chlorinated benzamides via either a radical or a cationic

  最近，水性胶束介质中的光催化为激活强碳卤键开辟了广阔的途径。然而，到目前为止，它主要探索了强烈的还原条件，将可用的化学空间限制为自由基或阴离子反应性。在这里，我们展示了一种可控的光催化策略，该策略通过自由基或阳离子途径引导氯化苯甲酰胺的反应，从而实现化学发散的 C-H 芳基化或N-脱烷基化。该催化系统在温和的条件下运行，亚甲基蓝作为光催化剂，蓝色 LED 作为光源。介绍了决定底物反应性、选择性和初步机理研究的因素。
• Nickel or Phenanthroline Mediated Intramolecular Arylation of sp³ C–H Bonds Using Aryl Halides
  作者：William C. Wertjes、Lydia C. Wolfe、Peter J. Waller、Dipannita Kalyani

  DOI：10.1021/ol402869h

  日期：2013.12.6

  the intramolecular arylation of sp3 C–H bonds adjacent to nitrogen using aryl halides is described. Arylation was accomplished using either Ni(COD)2 or 1,10-phenanthroline in substoichiometric amounts, and the reaction conditions were applied to a variety of electronically differentiated benzamide substrates. Preliminary studies suggest a mechanism involving aryl and alkyl radical intermediates.

  描述了使用芳基卤化物开发与氮相邻的 sp 3 C-H 键的分子内芳基化。使用亚化学计量量的Ni(COD) 2或 1,10-菲咯啉完成芳基化，并将反应条件应用于各种电子分化的苯甲酰胺底物。初步研究表明涉及芳基和烷基自由基中间体的机制。
• Steric effect of carboxylic acid ligands on Pd-catalyzed C–H activation reactions
  作者：Tetsuaki Fujihara、Atsushi Yoshida、Motoi Satou、Yutaka Tanji、Jun Terao、Yasushi Tsuji

  DOI：10.1016/j.catcom.2016.06.003

  日期：2016.9

  Various carboxylic acids with different substitution patterns were used as ligands in intra- and intermolecular Pd-catalyzed C–H activation reactions to investigate steric effect of the ligands. Bulky carboxylic acids suppress deactivation of Pd catalysts.

  在Pd分子内和分子间催化的CH活化反应中，各种具有不同取代方式的羧酸用作配体，以研究配体的空间效应。庞大的羧酸可抑制Pd催化剂的失活。