7,7-二氯二环[3.2.0]庚-2-烯-6-酮 | 5307-99-3

• 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 - 有机氧化合物
• 中文名称: 7,7-二氯二环[3.2.0]庚-2-烯-6-酮
• 中文别名: 7,7-二氯二环(3.2.0 )庚-2-烯-6-酮；7,7-二氯二环[3.2.]庚-2-烯-6-酮
• 英文名称: (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
• 英文别名: 7,7-dichlorobicyclo<3.2.0>hept-2-en-6-one；7,7-Dichlorbicyclo<3.2.0>hept-2-en-6-on；7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-one
• CAS: 5307-99-3
• 化学式: C₇H₆Cl₂O
• mdl: MFCD00013738
• 分子量: 177.03
• InChiKey: JBPBARAOHIDZPU-UHFFFAOYSA-N

物化性质

• 沸点：
  58-64 °C (0.5 mmHg)
• 密度：
  1.44±0.1 g/cm3(Predicted)
• 闪点：
  127-128°C/25mm
• 稳定性/保质期：

  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2914700090
• 安全说明：
  S26,S36/37/39
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险品运输编号：
  3265
• 危险性描述：
  H302,H314
• 储存条件：
  请将药品存放在4℃以下避光、阴凉干燥且密封的地方保存。

SDS

Name:	7 7-Dichlorobicyclo(3.2.0)hept-2-enone Material Safety Data Sheet
Synonym:	None
CAS:	5307-99-3

Section 1 - Chemical Product MSDS Name:7 7-Dichlorobicyclo(3.2.0)hept-2-enone Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5307-99-3	7,7-Dichlorobicyclo(3.2.0)hept-2-enone	98	226-165-0

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.
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:
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.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. 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. Avoid contact with eyes, skin, and clothing. Avoid breathing vapor or mist.
Storage:
Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.)

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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# 5307-99-3: Personal Protective Equipment Eyes: Wear chemical splash goggles.
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: Liquid
Color: clear brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 127 - 129 deg C @ 25 mmHg
Freezing/Melting Point: Not available.
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: C7H6Cl2O
Molecular Weight: 177.03

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
High temperatures.
Incompatibilities with Other Materials:
Strong bases, strong oxidizing agents, strong reducing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5307-99-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
7,7-Dichlorobicyclo(3.2.0)hept-2-enone - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 5307-99-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5307-99-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5307-99-3 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：

  7,7-二氯二环[3.2.0]庚-2-烯-6-酮 在 水 、 三乙胺 、 potassium carbonate 作用下， 以 叔丁醇 为溶剂， 反应 3.5h， 以52%的产率得到(+/-)-2-formylcyclopent-2-enecarboxylic acid
  参考文献：
  名称：

  （±）-7,7-dichlorobicyclo [3.2.0] hept-2-en-6-one的邻位取代的环戊烯和环戊烯酮

  摘要：

  （±）-7,7-二氯双环[3.2.0]庚-2-烯-6-酮在叔丁醇与水和三乙胺的混合物中溶剂化，然后依次用K 2 CO 3，NaBH 4处理，和CH 2 N 2，得到2-（羟甲基）环戊-2-烯-1-羧酸甲酯，将其进行氢化还原，环氧化，三氯乙酰亚胺化和乙酰化。2-（乙酰氧基甲基）环戊-2-烯-1-羧酸甲酯与氧化铬（VI）-3,5-二甲基吡唑配合物的烯丙基氧化得到2-（乙酰氧基甲基）-4-氧代环戊-2-烯-1-甲酸甲酯羧酸盐和甲基（1 R *，2 R *，5 R将*）-1-（羟甲基）-6-氧杂双环[3.1.0]-己烷-2-羧酸酯转化为合成脱氧entecavir和肉瘤霉素甲酯的结构单元。

  DOI：

  10.1134/s1070428015030057
• 作为产物：
  描述：

  (1S,4S,5S)-7,7-dichloro-2,4-bis(trimethylsilyl)bicyclo[3.2.0]hept-2-en-6-one 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以37%的产率得到7,7-二氯二环[3.2.0]庚-2-烯-6-酮
  参考文献：
  名称：

  双（三甲基甲硅烷基）环戊二烯与二氯酮的反应，以及N-苯基马来酰亚胺与两个甲硅烷基化的甲基环戊二烯之间的狄尔斯-阿尔德反应

  摘要：

  双（三甲基甲硅烷基）环戊二烯与二氯酮反应，仅得到衍生自2，5-二甲硅烷基化的异构体（5）的加合物（7）。甲基（三甲基甲硅烷基）环戊二烯（18）和三甲基甲硅烷基甲基环戊二烯（21）得到狄尔斯-阿尔德加合物（19）和（20），（22）和（23），其中区域选择性不受甲硅烷基的影响。加合物（22）的环氧化和环氧化物的酸催化的开口导致在甲硅烷基的存在控制下的重排中形成外-亚甲基降冰片烷（26）。

  DOI：

  10.1039/p19810000684

文献信息

• Synthesis, structure-activity relationships, and mechanistic studies of 5-arylazo-tropolone derivatives as novel xanthine oxidase (XO) inhibitors
  作者：Daisuke Sato、Takuya Kisen、Mina Kumagai、Kiminori Ohta

  DOI：10.1016/j.bmc.2017.12.017

  日期：2018.1

  5-arylazotropolone derivatives as potential XO inhibitors. In vitro enzyme-inhibitory assays for XO revealed that 3-nitro derivative 1j showed the most potent XO inhibitory activity, which is by one order of magnitude more potent than allopurinol. An enzyme-kinetic study revealed that 1j inhibited the production of uric acid by XO both competitively and non-competitively. A docking-simulation study of 1j with

  黄嘌呤氧化酶（XO）是一种在活性位点包含钼的酶，催化嘌呤碱氧化为尿酸。尽管XO抑制剂被广泛用于治疗高尿酸血症和痛风，但在临床上仅极少数的此类化合物被用作治疗这些疾病的药物。鉴于托酚酮独特的理化性质，即其螯合作用和与羧酸相似的pKa值，我们合成了22种潜在的XO抑制剂5-芳基偶氮酮化合物。XO的体外酶抑制试验表明，3-硝基衍生物1j表现出最有效的XO抑制活性，比别嘌呤醇的效力高一个数量级。酶动力学研究表明1jXO竞争性和非竞争性抑制了尿酸的产生。1j与XO的对接模拟研究表明，托酚酮环的羰基和羟基与充当钼配体的羟基和XO活性位点周围的氨基酸残基相互作用。
• [EN] PYRAZOLE DERIVATIVES AS BROMODOMAIN INHIBITORS<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILISÉS EN TANT QU'INHIBITEURS DE BROMODOMAINE
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2018158212A1

  公开（公告）日：2018-09-07

  The present invention is directed to pyrazole derivatives, pharmaceutical compositions comprising the compounds and the use of the compounds or the compositions in the treatment of various diseases

  本发明涉及吡唑衍生物，包括该化合物的药物组合物以及在治疗各种疾病中使用该化合物或组合物。
• Acid-catalyzed rearrangement of cyclobutanols. Syntheses of chrysenes, cyclopentenophenanthrenes, and diarylmethanes
  作者：Edward Lee-Ruff、Alan C. Hopkinson、Hira Kazarians-Moghaddam、Brij Gupta、Morris Katz

  DOI：10.1139/v82-026

  日期：1982.1.15

  Acid-catalyzed reactions of 8-aryl or 8,8-diarylbicyclo[4.2.0]oct-2-en-7-ols lead to tetrahydrophenanthrene derivatives. For example 8-(1-naphthyl)-bicyclo[4.2.0]oct-2-en-7-ols give substituted chrysenes in methanesulphonic acid. In the case of the homologous 7-aryl or 7,7-diarylbicyclo[3.2.0]hept-2-en-6-ols a novel transformation to diarlymethanes is observed. A mechanism is proposed which accounts

  8-芳基或8,8-二芳基双环[4.2.0] oct-2-en-7-ols 的酸催化反应生成四氢菲衍生物。例如，8-(1-萘基)-双环[4.2.0]oct-2-en-7-ols 在甲磺酸中产生取代的芘。在同源 7-芳基或 7,7-二芳基双环 [3.2.0]hept-2-en-6-ols 的情况下，观察到了向二芳基甲烷的新转化。提出了一种机制来解释在这些重排中观察到的产物分布。
• A practical route to both enantiomers of bicyclo[3.3.0]oct-2-en-7-one and their use for the synthesis of key trisubstituted cyclopentanes
  作者：David Cousin、John Mann

  DOI：10.1016/j.tet.2008.01.134

  日期：2008.4

  We describe new methodology for the synthesis of both enantiomers of 7,7-dichlorobicyclo[3.2.0]hep-2-en-6-one and conversion of these compounds into stereochemically defined bicyclo[3.3.0]oct-2-en-7-ones and thence trisubstituted cyclopentanes. These are key intermediates for the synthesis of prostanoids, brefeldin and other cyclopentane-containing natural products.

  我们描述了7,7-二氯双环[3.2.0] hep-2-en-6-one的两个对映异构体的合成以及将这些化合物转化为立体化学定义的双环[3.3.0] oct-2-en-的新方法7-ones，然后是三取代的环戊烷。这些是合成前列腺素，布雷菲德菌素和其他含环戊烷的天然产物的关键中间体。
• 一种corey内酯二醇的制备方法
  申请人：沈阳欧利康化学科技有限公司

  公开号：CN107573309A

  公开（公告）日：2018-01-12

  本发明提供一种corey内酯二醇的制备方法，涉及一种醇的合成技术领域。该发明由包含下述步骤制备而成：解聚、环化、脱氯、拆分、氧化、prins反应、水解。本发明简便易行、易于操作，有利于工业化生产。

表征谱图