cis-1,2-cyclobutane dicarboxylic anhydride | 4462-96-8

• 物质功能分类: 化学试剂 - 有机试剂 - 羧酸酐
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: cis-1,2-cyclobutane dicarboxylic anhydride
• 英文别名: (1R,5S)-3-oxabicyclo[3.2.0]heptane-2,4-dione
• CAS: 4462-96-8
• 化学式: C₆H₆O₃
• 分子量: 126.112
• InChiKey: NMNZZIMBGSGRPN-ZXZARUISSA-N

物化性质

• 熔点：
  73 °C
• 沸点：
  90-100 °C(Press: 0.5 Torr)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2917209090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：2-8°C，建议使用惰性气体保护。

SDS

Name:	Perhydrocyclobuta[c]furan-1 3-dione 95+% Material Safety Data Sheet
Synonym:	Cyclobutane-1,2-dicarboxylic acid anhydrid
CAS:	4462-96-8

Section 1 - Chemical Product MSDS Name:Perhydrocyclobuta[c]furan-1 3-dione 95+% Material Safety Data Sheet
Synonym:Cyclobutane-1,2-dicarboxylic acid anhydrid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4462-96-8	Perhydrocyclobuta[c]furan-1,3-dione	95+%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under an inert atmosphere.

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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# 4462-96-8: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 60 - 65 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H6O3
Molecular Weight: 126

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Oxidizing agents, bases, amines.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4462-96-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Perhydrocyclobuta[c]furan-1,3-dione - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 4462-96-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4462-96-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4462-96-8 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

制备方法与用途

环丁烷-1,2-二甲酸酐是一种合成化合物，已证明其为醇类不对称合成的有效催化剂。它可以用于环丁烷或环酮等环状化合物的立体选择性合成。

反应信息

• 作为反应物：
  描述：

  cis-1,2-cyclobutane dicarboxylic anhydride 在 lithium aluminium tetrahydride 、 乙醚 、 异丙醇 作用下， 生成 3-hexyl-3-methyl-3-azonia-bicyclo[3.2.0]heptane; iodide
  参考文献：
  名称：

  Hypotensive Agents. VII.¹ Azabicyclo[3.2.0]heptane Derivatives²

  摘要：

  DOI：

  10.1021/jo01360a029
• 作为产物：
  描述：

  1,1,2,2-Tetracarboxy-cyclobutan 生成 cis-1,2-cyclobutane dicarboxylic anhydride
  参考文献：
  名称：

  CXCIX.—某些二溴四羧酸酯对丙二酸乙酯，乙基四羧酸乙酯和类似物质的钠衍生物的作用

  摘要：

  DOI：

  10.1039/jr9280001513

文献信息

• [EN] COMPOUNDS THAT INHIBIT MCL-1 PROTEIN<br/>[FR] COMPOSÉS INHIBANT LA PROTÉINE MCL-1
  申请人：AMGEN INC

  公开号：WO2018183418A1

  公开（公告）日：2018-10-04

  Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (I), or a stereoisomer thereof; and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.

  本文提供了髓样细胞白血病1蛋白（Mcl-1）抑制剂，其制备方法，相关的药物组合物，以及使用这些物质的方法。例如，本文提供了化合物的化学式（I）或其立体异构体；以及这些化合物的药用盐和含有这些化合物的药物组合物。本文提供的化合物和组合物可以用于治疗癌症等疾病或症状。
• Synthesis and Anxiolytic Activity of N-Substituted Cyclic Imides(1R*,2S*,3R*,4S*)-N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-2,3-bicyclo(2.2.1)heptanedicarboximide(Tandospirone) and Related Compounds.
  作者：Kikuo ISHIZUMI、Atsuyuki KOJIMA、Fujio ANTOKU

  DOI：10.1248/cpb.39.2288

  日期：——

  The in vitro binding affinities of these compounds were also examined for 5-HT1A receptor sites. Structure-activity relationships within these series are discussed. One of these compounds, (1R*,2S*,-3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3- bicyclo[2.2.1]heptanedicarboximide (1: tandospirone), was found to be equipotent with buspirone in its anxiolytic activity and more anxio-selective

  合成了一系列带有ω-（4-芳基和4-杂芳基-1-哌嗪基）烷基的环状酰亚胺，并在体内测试其抗焦虑活性。还检查了这些化合物的体外结合亲和力的5-HT1A受体位点。讨论了这些系列中的构效关系。这些化合物之一，（1R *，2S *，-3R *，4S *）-N- [4- [4-（4-嘧啶基）-1-哌嗪基]丁基] -2,3-双环[2.2.1已发现]庚烷二甲酰亚胺（1：tandospirone）与丁螺环酮具有相同的抗焦虑活性，并且比丁螺环酮和地西epa具有更高的选择性。Tandospirone（1）目前正在作为一种选择性抗焦虑药进行临床评估。
• The Synthesis of Unsubstituted Cyclic Imides Using Hydroxylamine under Microwave Irradiation
  作者：Ellis Benjamin、Yousef Hijji

  DOI：10.3390/molecules13010157

  日期：——

  Unsubstituted cyclic imides were synthesized from a series of cyclic anhydrides,hydroxylamine hydrochloride (NH2OH·HCl), and 4-N,N-dimethylamino-pyridine (DMAP,base catalyst) under microwave irradiation in monomode and multimode microwaves. Thisnovel microwave synthesis produced high yields of the unsubstituted cyclic imides forboth the monomode (61 - 81%) and multimode (84 - 97%) microwaves.

  未取代的环状亚胺通过一系列环状酐、盐酸羟胺(NH2OH·HCl)以及4-N,N-二甲氨基吡啶(DMAP，碱催化剂)在单模和多模微波辐照下合成。这种新颖的微波合成方法在单模微波（产率61%-81%）和多模微波（产率84%-97%）条件下均能产生高产量的未取代环状亚胺。
• Highly Enantioselective Hydrogenative Desymmetrization of Bicyclic Imides Leading to Multiply Functionalized Chiral Cyclic Compounds
  作者：Masato Ito、Chika Kobayashi、Akio Himizu、Takao Ikariya

  DOI：10.1021/ja105048c

  日期：2010.8.25

  Highly enantioselective hydrogenative desymmetrization of bicyclic imides has been developed with chiral Cp*Ru(PN) catalysts. The present hydrogenation directly provides stereochemically well-defined cyclic compounds with excellent enantiomeric exessses, which might otherwise require a detour to reach.

  使用手性 Cp*Ru(PN) 催化剂开发了双环酰亚胺的高度对映选择性氢化去对称化。本氢化直接提供立体化学明确定义的环状化合物，具有优异的对映异构体，否则可能需要绕道而行。
• [EN] TRIAZACYCLODODECANSULFONAMIDE ("TCD")-BASED PROTEIN SECRETION INHIBITORS<br/>[FR] INHIBITEURS DE SÉCRÉTION DE PROTÉINE À BASE DE TRIAZACYCLODODÉCANSULFONAMIDE ("TCD")
  申请人：KEZAR LIFE SCIENCES

  公开号：WO2019178510A1

  公开（公告）日：2019-09-19

  Provided herein are triazacyclododecansulfonamide ("TCD")-based protein secretion inhibitors, such as inhibitors of Sec61, methods for their preparation, related pharmaceutical compositions, and methods for using the same. For example, provided herein are compounds of Formula (I) and pharmaceutically acceptable salts and compositions including the same. The compounds disclosed herein may be used, for example, in the treatment of diseases including inflammation and/or cancer.

  本文提供了基于三氮杂环十二烷磺酰胺（"TCD"）的蛋白质分泌抑制剂，例如Sec61的抑制剂，其制备方法，相关的药物组合物，以及使用它们的方法。例如，本文提供了符合Formula（I）的化合物及其药用盐和包括它们的组合物。本文披露的化合物可以用于治疗炎症和/或癌症等疾病。