N-[2-(二甲氨基)-2-氧乙基]-氨基甲酸-1,1-二甲基乙酯 | 72287-76-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-[2-(二甲氨基)-2-氧乙基]-氨基甲酸-1,1-二甲基乙酯
• 英文名称: tert-butyl (2-(dimethylamino)-2-oxoethyl)carbamate
• 英文别名: N-(tert-butoxycarbonyl)glycine N,N-dimethylamide；tert-butyl N-[2-(dimethylamino)-2-oxoethyl]carbamate
• CAS: 72287-76-4
• 化学式: C₉H₁₈N₂O₃
• 分子量: 202.254
• InChiKey: PIHHWCMBAMTJAK-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68°
• 沸点：
  313.5±25.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924199090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: tert-Butyl N-[(dimethylcarbamoyl)methyl]carbamate
Synonyms: tert-butyl N-[2-(dimethylamino)-2-oxoethyl]carbamate

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: tert-Butyl N-[(dimethylcarbamoyl)methyl]carbamate
CAS number: 72287-76-4

---

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.
Storage: Store in closed vessels, refrigerated.

---

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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H18N2O3
Molecular weight: 202.3

---

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.

---

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-[2-(二甲氨基)-2-氧乙基]-氨基甲酸-1,1-二甲基乙酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N,N-二甲基甘氨酰胺
  参考文献：
  名称：

  Highly Selective and Sensitive Detection of Biogenic Defense Phytohormone Salicylic Acid in Living Cells and Plants Using a Novel and Viable Rhodamine-Functionalized Fluorescent Probe

  摘要：

  Detecting plant-derived signal molecules using fluorescent probes is a key topic and a huge challenge for scientists. Salicylic acid (SA), a vital plant-derived defense hormone, can activate global transcriptional reprogramming to systemically express a network of prominent pathogenesis-related proteins against invasive microorganisms. This strategy is called systemic acquired resistance (SAR). Therefore, monitoring the dynamic fluctuations of SA in subcellular microenvironments can advance our understanding of different physiological and pathological functions during the SA-induced SAR mechanism, thus benefiting the discovery and development of novel immune activators that contribute to crop protection. Here, detection of signaling molecule SA in plant callus tissues was first reported and conducted by a simple non-fluorescent rhodamine-tagged architecture bearing a flexible 2-amino-N,N-dimethylacetamide pattern. This study can markedly advance and promote the usage of fluorescent SA probes for distinguishing SA in the plant kingdom.

  DOI：

  10.1021/acs.jafc.9b06771
• 作为产物：
  描述：

  BOC-甘氨酸 在 三乙胺 作用下， 以 水 为溶剂， 生成 N-[2-(二甲氨基)-2-氧乙基]-氨基甲酸-1,1-二甲基乙酯
  参考文献：
  名称：

  Conformational Analysis of β-Turn Structure in Tetrapeptides Containing Proline or Proline Analogs

  摘要：

  In order to evaluate the influence of cyclic secondary amino acids on the stability of beta-turn structure, we have prepared Ac-Gly-L-Xxx-L-Leu-Gly-N(CH3)(2) (Xxx = Aze, 4-membered ring: 1, Xxx = Pro, 5-membered ring: 2, Xxx = Pip, 6-membered ring: 3). The NOE cross peaks that support beta-turn structure were observed in 1-3. The NOE cross peak between both terminals of the synthetic peptides, however, was observed only in the NOESY spectra of 2. This result indicates that 5-membered ring side chain in proline plays a very important role in the formation of beta-hairpin structure. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00529-7

文献信息

• LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism
  作者：Marie-Céline Frantz、Lucie P. Pellissier、Elsa Pflimlin、Stéphanie Loison、Jorge Gandía、Claire Marsol、Thierry Durroux、Bernard Mouillac、Jérôme A. J. Becker、Julie Le Merrer、Christel Valencia、Pascal Villa、Dominique Bonnet、Marcel Hibert

  DOI：10.1021/acs.jmedchem.8b00697

  日期：2018.10.11

  affinity and efficacy of representative ligands of the V1a and V2 vasopressin receptor subtypes (V1a-R and V2-R) and of the oxytocin receptor. Our results confirm the subtlety of the structure–affinity and structure–efficacy relationships around vasopressin/oxytocin receptor ligands and lead however to the first nonpeptide OT receptor agonist active in a mouse model of ASD after peripheral ip administration

  催产素（OT）及其受体（OT-R）与自闭症谱系障碍（ASD）的病因有关，并且OT-R是治疗干预的潜在目标。当前已经报道了极少的非肽催产素激动剂。它们的分子和体内药理学仍有待阐明，并且没有显示它们在改善与ASD相关的动物模型中的社会互动方面有效。为了合理设计中枢活性非肽全激动剂的设计，我们以系统的方式研究了V 1a和V 2加压素受体亚型（V 1a -R和V 2）的代表性配体的亲和力和功效的结构决定因素。-R）和催产素受体。我们的研究结果证实了血管加压素/催产素受体配体周围的结构亲和力和结构功效关系的微妙之处，但是导致了在外围腹膜内注射后在ASD小鼠模型中首个活性的非肽OT受体激动剂。
• Total Synthesis of (±)-Kainic Acid with an Aza-[2,3]-Wittig Sigmatropic Rearrangement as the Key Stereochemical Determining Step
  作者：James C. Anderson、Matthew Whiting

  DOI：10.1021/jo030101q

  日期：2003.8.1

  route to the kainoid skeleton is exemplified by the synthesis of (+/-)-kainic acid from 3-butyn-1-ol. The route relies on the aza-[2,3]-Wittig sigmatropic rearrangement to efficiently install the relative stereochemistry between C2-C3. The C4 stereocenter was derived from a diastereocontrolled iodolactonization. The aza-[2,3]-Wittig rearrangement potentially allows structural diversity at C3 and the

  由3-丁炔-1-醇合成（+/-）-海藻酸举例说明了通往类胡萝卜素骨架的灵活途径。该路线依赖于aza- [2,3] -Wittigσ重排，以有效地在C2-C3之间安装相对立体化学。C4立体中心源自非对映控制的碘内酯化。氮杂-[2，3]-维蒂希重排潜在地允许C3处的结构多样性，并且保持立体化学的甲苯磺酰基基团的置换允许C4处的结构多样性。发现在用高阶氰基铜酸盐试剂处理后，反式-C2羧酸官能团对于保持立体化学在C4上是最重要的。
• Photochemical and Additive-Free Coupling Reaction of α-Cumyl α-Keto Esters via Intermolecular C–H Bond Activation
  作者：Go Hirai、Mikiko Sodeoka、Eisuke Ota、Yu Mikame、Shigeru Nishiyama

  DOI：10.1055/s-0035-1561098

  日期：——

  simple alcohols, alkanes, ethers, and amides. Use of tertiary alkyl ester, α-cumyl ester, is the key for avoiding the known photo-degradation process. Intermolecular C–H bond activation and subsequent C–C bond formation were promoted by irradiation with an LED lamp (365 nm) without any additives. Among the coupling partners, reactions with sterically less demanding amides proceeded efficiently to provide

  我们开发了 α-酮酯与几种简单的醇、烷烃、醚和酰胺的光化学偶联反应。使用叔烷基酯、α-枯基酯是避免已知光降解过程的关键。用不含任何添加剂的 LED 灯（365 nm）照射促进分子间 C-H 键活化和随后的 C-C 键形成。在偶联伙伴中，与空间上要求较低的酰胺反应有效地进行，以提供独特的 N-酰基-β-氨基-α-羟基酸衍生物。在苯或丙酮作为溶剂中，与固体氨基酸衍生物的反应提供了四氢-1,4-二氮杂-2,5-二酮衍生物的前体。
• Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination
  作者：A. J. Metrano、N. C. Abascal、B. Q. Mercado、E. K. Paulson、S. J. Miller

  DOI：10.1039/c6cc01428c

  日期：——

  X-Ray crystallography and NMR spectroscopy were used to investigate the effect of primary structure on both secondary structure and enantioselectivity in peptide-based catalysts for an atroposelective bromination reaction.

  X射线晶体学和核磁共振光谱学被用来研究肽基催化剂在对映选择性溴化反应中的一级结构对二级结构和对映选择性的影响。
• Enantioselective Synthesis of 3-Arylquinazolin-4(3<i>H</i>)-ones via Peptide-Catalyzed Atroposelective Bromination
  作者：Matthew E. Diener、Anthony J. Metrano、Shuhei Kusano、Scott J. Miller

  DOI：10.1021/jacs.5b07726

  日期：2015.9.30

  atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional

  我们报告了一种含叔胺的 β-转角肽的开发，该肽可催化药物相关的 3-芳基喹唑啉-4(3H)-酮（喹唑啉酮）的间质选择性溴化，在广泛的底物范围内具有高水平的对映诱导作用。使用 X 射线晶体学和 2D-​​NOESY 实验探索了游离催化剂和肽-底物复合物的结构。还使用密度泛函理论计算研究了围绕手性苯胺轴的喹唑啉酮旋转势垒，并根据观察到的高对映选择性进行了讨论。机理研究还表明，最初的溴化事件是立体决定的，主要的一溴化物中间体是一种阻转异构稳定的单邻位取代异构体。立体异构稳定的一溴化物的观察刺激了三溴化物产物转化为其他阻转异构定义的感兴趣的产物。例如，(1) 脱卤 Suzuki-Miyaura 交叉偶联序列提供邻位芳基化衍生物，(2) 区域选择性 Buchwald-Hartwig 胺化程序安装对胺官能团。在这些后续转化过程中保留了立体化学信息。