2'-氨基-4',5'-亚甲二氧基苯乙酮 | 28657-75-2

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 2'-氨基-4',5'-亚甲二氧基苯乙酮
• 中文别名: 6-氨基-3,4-亚甲二氧基苯乙酮；6'-氨基-3',4'-(亚甲基二氧代)苯乙酮；5-乙酰-6-氨基-1,3-苯并二呋喃；2’-氨基-4’,5’-亚甲二氧基苯乙酮；2-氨基-4,5-亚甲二氧基苯乙酮
• 英文名称: 2-amino-4,5-methylenedioxy-acetophenone
• 英文别名: 6-amino-3,4-methylenedioxyacetophenone；1-(6-aminobenzo[d][1,3]dioxol-5-yl)ethanone；1-(6-aminobenzo[d][1,3]dioxol-5-yl)ethan-1-one；1-(6-amino-1,3-benzodioxol-5-yl)ethanone
• CAS: 28657-75-2
• 化学式: C₉H₉NO₃
• mdl: MFCD00075855
• 分子量: 179.175
• InChiKey: DWTHYSZSRJOMSC-UHFFFAOYSA-N

物化性质

• 熔点：
  168-171 °C
• 沸点：
  158 °C (30 mmHg)
• 密度：
  1.2822 (rough estimate)
• 溶解度：
  溶于二甲基甲酰胺
• 稳定性/保质期：
  常温常压下稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2932999099
• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  请将贮藏器密封存放于阴凉、干燥处，并确保工作环境具备良好通风或排气设施。

SDS

Name:	6-Amino-3 4-Methylenedioxyacetophenone 99+% (GC) Material Safety Data Sheet
Synonym:	None known
CAS:	28657-75-2

Section 1 - Chemical Product MSDS Name:6-Amino-3 4-Methylenedioxyacetophenone 99+% (GC) Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
28657-75-2	6-Amino-3,4-Methylenedioxyacetophenone	99+	249-131-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 28657-75-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: brown
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 168.00 - 171.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H9NO3
Molecular Weight: 179.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 28657-75-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Amino-3,4-Methylenedioxyacetophenone - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 28657-75-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 28657-75-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 28657-75-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2'-氨基-4',5'-亚甲二氧基苯乙酮 在 钯 palladium diacetate 、 甲酸 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 三(邻甲基苯基)磷 、 silver carbonate 、 三氯氧磷 、 苯酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 GENZ-644282抑制剂
  参考文献：
  名称：

  5-(2-Aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones:  Variation of N-Alkyl Substituents Modulates Sensitivity to Efflux Transporters Associated with Multidrug Resistance

  摘要：

  5H-8,9-Dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo [c, h]-[1,6]naphthyridin-6-one (ARC-111) has potent TOP1-targeting activity and pronounced antitumor activity. Several analogues of ARC-111 were synthesized with NH2, N-alkyl, N,N-dialkyl, pyrrolidinyl, piperidinyl, and piperazinyl substituents at the 2-position of the 5-ethyl group. The relative TOP1-targeting activity and cytotoxicity of these structural analogues were assessed in RPMI8402 and P388 tumor cells and their camptothecin-resistant variants CPT-K5 and P388/CPT45, respectively. Potent TOP1-targeting activity was retained within a series of mono N-alkyl analogues that included NHCH2CH3, NHCH(CH3)(2), and NHC(CH3)(3). TOP1-targeting activity was diminished by the presence of a N-benzyl moiety. In a comparison of a series of N-alkyl-N-isopropyl analogues, activity decreased in the order CH3 > CH2CH3 > CH(CH3)(2). Cytotoxicity in RPMI8402 and P388 did correlate with TOP1-targeting activity. Cytotoxic activity was also determined in KB3-1 cells and its variants KB/V-1 and KBH5.0. As KB/V-1 cells overexpress MDR1 and KBH5.0 cells overexpress BCRP, decreased cytotoxicity in these cell lines relative to the parent cell line is indicative of compounds that are substrates for these efflux transporters. In view of their diminished cytotoxicity in KB/V-1 cells, it appears that the likely demethylated metabolites of ARC-111, i.e., where NH2 or NHCH3 replaces the N(CH3)(2) at the 2-position of the 5-ethyl substituent, are substrates for MDR1. In contrast, no significant difference in cytotoxicity among these three cell lines was observed with other N-alkyl analogues, including NHC2H5, NHCH(CH3)(2), NHC(CH3)(3), N(CH3)(2), N(CH2CH3)(2), NCH3(CH(CH)(3))(2)), and either the pyrrolidinyl or the piperidinyl analogues. The 2-(piperazinyl) analogues were associated with diminished cytotoxicity in KB/V-1 cells, suggesting that the second basic amino substituent is associated with their recognition as substrates by MDR1. Comparative studies on the antitumor activity of ARC-111 and its N-demethylated derivatives (the NHCH3 and NH2 analogues) against SJ-BT45 medulloblastoma xenografts in scid mice revealed that the secondary amine metabolite is at least as active as ARC-111 in vivo, although the primary amine derivative was significantly less potent.

  DOI：

  10.1021/jm049447z
• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 palladium 10% on activated carbon 、 氢气 、 硝酸 作用下， 以 硝基甲烷 、 乙醇 为溶剂， 反应 18.5h， 生成 2'-氨基-4',5'-亚甲二氧基苯乙酮
  参考文献：
  名称：

  [EN] CAMPTOTHECIN DERIVATIVE, AND PHARMACEUTICAL COMPOSITION AND USE THEREOF
  [FR] DÉRIVÉ DE CAMPTOTHÉCINE, COMPOSITION PHARMACEUTIQUE ET LEUR UTILISATION
  [ZH] 喜树碱衍生物、其药物组合物及其应用

  摘要：

  提供了式(I)所示化合物、或其立体异构体或药学上可接受的盐、其药物组合物，以及它们在抗肿瘤方面的用途。

  公开号：

  WO2023020605A1

文献信息

• Ru(ii)-catalyzed intermolecular ortho-C–H amidation of aromatic ketones with sulfonyl azides
  作者：M. Bhanuchandra、M. Ramu Yadav、Raja K. Rit、Malleswara Rao Kuram、Akhila K. Sahoo

  DOI：10.1039/c3cc41915k

  日期：——

  Ru(II)-catalyzed intermolecular ortho-C–H amidation of weakly coordinating aromatic ketones with sulfonyl azides is reported. The developed reaction protocol can be extended to various substituted aromatic ketones to afford a wide range of desired C–N bond formation products in good yields.

  报道了Ru(II)催化下，弱配位芳香酮与磺酰叠氮之间的分子间邻位C–H酰胺化反应。该反应方案可以扩展到各种取代的芳香酮，以良好产率获得大量期望的C–N键形成产物。
• Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer­-Type Transformation
  作者：Jianbo Wang、Xi Wang、Yan Xu、Yujing Zhou、Yan Zhang

  DOI：10.1055/s-0033-1338659

  日期：——

  strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are

  摘要 报道了通过Sandmeyer型反应将氨基转化为三氟甲基的芳香族三氟甲基化的新策略。该转化包括用亚硝酸叔丁酯和盐酸将芳族胺重氮化以形成芳基重氮氯化物，然后在低温下用三氟甲基银进行三氟甲基化。各种容易获得的芳族胺在温和条件下均能平稳转化。 报道了通过Sandmeyer型反应将氨基转化为三氟甲基的芳香族三氟甲基化的新策略。该转化包括用亚硝酸叔丁酯和盐酸将芳族胺重氮化以形成芳基重氮氯化物，然后在低温下用三氟甲基银进行三氟甲基化。各种容易获得的芳族胺在温和条件下均能平稳转化。
• Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin
  申请人：——

  公开号：US20020095041A1

  公开（公告）日：2002-07-18

  Biphenylsulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, bicyclic or tricyclic carbon or heterocyclic ring biphenylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.

  提供了二苯基磺胺类化合物和调节或改变内皮素家族肽活性的方法。具体包括使用双环或三环碳或杂环环二苯基磺胺类化合物的方法，通过将该磺胺类化合物与内皮素受体接触来抑制内皮素肽与内皮素受体的结合。还提供了通过给予有效剂量的这些磺胺类化合物或其前药来治疗内皮素介导的疾病的方法，这些化合物能够抑制或增加内皮素的活性。
• Easy α-alkylation of ketones with alcohols through a hydrogen autotransfer process catalyzed by RuCl2(DMSO)4
  作者：Ricardo Martínez、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tet.2006.07.013

  日期：2006.9

  indicate that the process goes through the oxidation of the alcohols with ruthenium (after a previous deprotonation) to yield the corresponding aldehyde and a ruthenium hydride intermediate. In turn, the aldehyde suffers a classical aldol reaction with the starting ketone to form the corresponding α,β-unsaturated ketone, which finally is reduced through a Michael-type addition by the aforementioned ruthenium

  酮与醇的亲电子α-烷基化是通过RuCl 2（DMSO）4催化的氢自动转移过程完成的。仅通过选择合适的起始酮（分别为甲基酮或双环亚甲基酮）以及喹啉（通过使用2-氨基苄醇衍生物）或相应的醇，该反应即可生成简单的烷基化酮或α，β-不饱和酮。通过添加额外当量的初始醇衍生而来。在最后一种情况下，在上述烷基化过程之后，羰基化合物还原。机理研究似乎表明该过程经历了醇与钌的氧化（在先前的去质子化之后），得到了相应的醛和氢化钌中间体。反过来，醛与起始酮发生经典的醛醇缩合反应，形成相应的α，β-不饱和酮，
• Synthesis of the antitumoural agent batracylin and related isoindolo[1,2-b]quinazolin-12(10H)-ones
  作者：Carlos M. Martínez-Viturro、Domingo Domínguez

  DOI：10.1016/j.tetlet.2006.11.168

  日期：2007.2

  The synthesis of batracylin and related isoindolo[1,2-b]quinazolin-12-ones from easily accessible o-acylanilines is reported. The preparation of these tetracyclic compounds through a Mitsunobu reaction followed by spontaneous cyclodehydration shows the ability of this methodology to afford good yields of a wide variety of diversely 7, 8, 9, 10-substituted isoindoloquinazolinones in two steps.

  据报道，从容易获得的邻苯丙氨酸类化合物中合成巴统西林和相关的异吲哚并[1,2 - b ]喹唑啉-12-酮。通过Mitsunobu反应然后自发环脱水制备这些四环化合物，表明该方法能够分两步提供多种多样的7、8、9、10取代异吲哚并喹唑啉酮的良好收率。

表征谱图