顺-N-(4-氯丁烯基)邻苯二甲酰亚胺 | 84347-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 顺-N-(4-氯丁烯基)邻苯二甲酰亚胺
• 英文名称: (Z)-N-(4-chloro-2-butenyl)phthalimide
• 英文别名: (Z)-2-(4-Chlorobut-2-en-1-yl)isoindoline-1,3-dione；2-[(Z)-4-chlorobut-2-enyl]isoindole-1,3-dione
• CAS: 84347-67-1
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: VSGHWUAHVBTJIU-ARJAWSKDSA-N

物化性质

• 熔点：
  79°C
• 沸点：
  374.2±35.0 °C(Predicted)
• 密度：
  1.2385 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2925190090
• 储存条件：
  存放于0至6℃阴凉干燥处。

SDS

Name:	cis-N-(4-Chlorobutenyl)Phthalimide 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	84347-67-1

Section 1 - Chemical Product MSDS Name:cis-N-(4-Chlorobutenyl)Phthalimide 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
84347-67-1	cis-N-(4-Chlorobutenyl)Phthalimide	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Light sensitive.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. 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light.
Storage:
Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.) Store protected from light.

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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# 84347-67-1: 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:
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: Crystalline powder
Color: light brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
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: C12H10ClNO2
Molecular Weight: 235.5285

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions. Light sensitive.
Conditions to Avoid:
Incompatible materials, light, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 84347-67-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
cis-N-(4-Chlorobutenyl)Phthalimide - 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.
WGK (Water Danger/Protection)
CAS# 84347-67-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 84347-67-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 84347-67-1 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：

  顺-N-(4-氯丁烯基)邻苯二甲酰亚胺 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 以60%的产率得到cis-4-chloro-2,3-epoxy-1-phthalimidobutane
  参考文献：
  名称：

  新型不饱和无环和环氧化物核苷类似物的合成，X射线晶体结构研究，抗病毒和细胞抑制作用评估。

  摘要：

  合成了一系列新颖的嘌呤和嘧啶核苷类似物，其中糖部分被4-氨基-2-丁烯基（2-6和10-18）和环氧乙烷基（8和20）间隔基取代。不饱和无环核苷类似物的Z-（2-6）和E-异构体（10-18）是通过将2和6个取代的嘌呤和5个取代的尿嘧啶碱基与Z-（1）或E-邻苯二甲酰亚胺缩合而合成的（9）前体。环氧乙烷基核苷类似物（8和20）是通过1和9与间氯过氧苯甲酸环氧化并随后与腺嘌呤偶联而获得的。对新化合物的抗病毒和抗肿瘤细胞活性进行了评估。在烯属核苷类似物中，含有4-氨基-2-丁烯基侧链的腺嘌呤的Z-异构体（6）表现出最佳的细胞抑制活性，尤其是对结肠癌的抑制作用（SW 620，IC50 = 26 microM）。它的E-异构体15除了对结肠癌（SW 620，IC50 = 56.5 microM）细胞有轻微抑制作用外，对恶性肿瘤细胞系没有任何抗增殖活性。通常，Z-异构体显示出比相应的E-异构体更好的

  DOI：

  10.1016/j.bmc.2006.07.033
• 作为产物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 potassium phtalimide 以 N,N-二甲基甲酰胺 为溶剂， 以28%的产率得到顺-N-(4-氯丁烯基)邻苯二甲酰亚胺
  参考文献：
  名称：

  手性支架配体在催化对映选择性加氢甲酰化中的应用

  摘要：

  β-氨基醛的合成是通过 PMP 保护的烯丙胺的对映选择性加氢甲酰化来实现的。该反应是通过使用与底物共价可逆结合的鳞片支架配体来完成的。这些配体的行为类似于手性助剂，因为它们在加氢甲酰化过程中共价连接到底物上；然而，与传统的不对称配体类似，它们可以以催化量使用。二取代烯烃的直接加氢甲酰化在温和条件（35 °C 和 50 psi CO/H(2)）下进行，Z-烯烃具有优异的对映选择性（高达 93% ee）。

  DOI：

  10.1021/ja107433h

文献信息

• Thromboxane synthetase inhibitors and antihypertensive agents. 1. N-[(1H-imidazol-1-yl)alkyl]aryl amides and N-[(1H-1,2,4-triazol-1-yl)alkyl]aryl amides
  作者：William B. Wright、Jeffery B. Press、Peter S. Chan、Joseph W. Marsico、Margie F. Haug、Judy Lucas、Jess Tauber、Andrew S. Tomcufcik

  DOI：10.1021/jm00154a017

  日期：1986.4

  formation. The most interesting thromboxane synthetase inhibitors prepared were 4-chloro-, 4-(trifluoromethyl)-, and 4-bromobenzamide derivatives of (1H-imidazol-1-yl)alkylamines with C5-C8 alkyl chains separating the heterocycle from the amide moiety, while the most active antihypertensive agents were 3- or 4-chloro-, -bromo, or -(trifluoromethyl)benzamides with C3 alkyl chains. The best thromboxane

  制备标题化合物以研究其作为血栓烷合成酶抑制剂以及降压药的潜力。制备咪唑VIII和三唑X以检查芳族取代，链长和杂环取代对生物活性的影响。咪唑VIII和三唑X是不抑制前列环素形成的血栓烷合成酶抑制剂。制备的最有趣的血栓烷合成酶抑制剂是（1H-咪唑-1-基）烷基胺的4-氯-，4-（三氟甲基）-和4-溴苯甲酰胺衍生物，其C5-C8烷基链将杂环与酰胺部分分开，而最具活性的降压药是带有C3烷基链的3-或4-氯-，-溴或-（三氟甲基）苯甲酰胺。
• Synthesis of Novel Tetrahydroisoquinoline CXCR4 Antagonists with Rigidified Side-Chains
  作者：Edgars Jecs、Eric J. Miller、Robert J. Wilson、Huy H. Nguyen、Yesim A. Tahirovic、Brook M. Katzman、Valarie M. Truax、Michelle B. Kim、Katie M. Kuo、Tao Wang、Chi S. Sum、Mary E. Cvijic、Gretchen M. Schroeder、Lawrence J. Wilson、Dennis C. Liotta

  DOI：10.1021/acsmedchemlett.7b00406

  日期：2018.2.8

  potent TIQ15-derived CXCR4 antagonists is reported. In this investigation, the TIQ15 side-chain was constrained to improve its drug properties. The cyclohexylamino congener 15a was found to be a potent CXCR4 inhibitor (IC50 = 33 nM in CXCL12-mediated Ca2+ flux) with enhanced stability in liver microsomes and reduced inhibition of CYP450 (2D6). The improved CXCR4 antagonist 15a has potential therapeutic

  报道了有效的TIQ15衍生的CXCR4拮抗剂的结构活性关系研究。在这项研究中，TIQ15侧链被限制以改善其药物特性。发现环己基氨基同源物15a是有效的CXCR4抑制剂（在CXCL12介导的Ca 2+通量中IC 50 = 33 nM ），在肝微粒体中的稳定性增强，并且对CYP450（2D6）的抑制作用降低。改进的CXCR4拮抗剂15a具有作为单药或联合抗癌疗法的潜在治疗应用。
• [EN] CHEMOKINE CXCR4 RECEPTOR MODULATORS AND USES RELATED THERETO<br/>[FR] MODULATEURS DU RÉCEPTEUR CXCR4 DE CHIMIOKINE ET LEURS UTILISATIONS
  申请人：UNIV EMORY

  公开号：WO2018156595A1

  公开（公告）日：2018-08-30

  The disclosure relates to chemokine CXCR4 receptor modulators and uses related thereto. The receptor modulators can be formulated to form pharmaceutical compositions comprising the disclosed compounds or pharmaceutically acceptable salts or prodrugs thereof. The compositions may be used for managing CXCR4 related conditions, typically prevention or treatment of viral infections abnormal cellular proliferation, retinal degeneration, inflammatory diseases, or as an immunostimulant or immunosuppressant or for managing cancer and may be administered with another active ingredient such as an antiviral agent or chemotherapeutic agent.

  该披露涉及趋化因子CXCR4受体调节剂及其相关用途。这些受体调节剂可以配制成包含所披露的化合物或其药学上可接受的盐或前药的药物组合物。这些组合物可用于管理与CXCR4相关的疾病，通常用于预防或治疗病毒感染、异常细胞增殖、视网膜退化、炎症性疾病，或作为免疫刺激剂或免疫抑制剂，或用于癌症管理，并可与另一种活性成分一起给药，如抗病毒药物或化疗药物。
• Synthesis and Evaluation of Novel Tetrahydronaphthyridine CXCR4 Antagonists with Improved Drug-like Profiles
  作者：Edgars Jecs、Yesim A. Tahirovic、Robert J. Wilson、Eric J. Miller、Michelle Kim、Valarie Truax、Huy H. Nguyen、Nicholas S. Akins、Manohar Saindane、Tao Wang、Chi S. Sum、Mary E. Cvijic、Gretchen M. Schroeder、Samantha L. Burton、Cynthia A. Derdeyn、Lingjie Xu、Yi Jiang、Lawrence J. Wilson、Dennis C. Liotta

  DOI：10.1021/acs.jmedchem.1c01564

  日期：2022.3.10

  Our first-generation CXCR4 antagonist TIQ15 was rationally modified to improve drug-like properties. Introducing a nitrogen atom into the aromatic portion of the tetrahydroisoquinoline ring led to several heterocyclic variants including the 5,6,7,8-tetrahydro-1,6-naphthyridine series, greatly reducing the inhibition of the CYP 2D6 enzyme. Compound 12a demonstrated the best overall properties after

  我们的第一代CXCR4拮抗剂TIQ15经过合理修饰，改善了类药特性。将氮原子引入四氢异喹啉环的芳香部分会产生多种杂环变体，包括5,6,7,8-四氢-1,6-萘啶系列，大大降低了CYP 2D6酶的抑制。在一系列生化分析（包括 CXCR4 拮抗作用、CYP 2D6 抑制作用、代谢稳定性和渗透性）中分析一系列异构四氢萘啶类似物后，化合物12a显示出最佳的整体特性。12a的丁胺侧链被各种亲脂基团取代以改善渗透性。这些努力最终发现化合物30是一种有效的 CXCR4 拮抗剂 (IC 50 = 24 nM)，可降低 CYP 2D6 活性，改善 PAMPA 通透性 (309 nm/s)，有效抑制人类免疫缺陷病毒进入 (IC 50 = 7 nM) ）、与 AMD11070 和 TIQ15 相比，更清晰的体外脱靶安全性、更低的人醚 a-go-go 相关基因通道活性以及更高的小鼠口服生物利用度（% F PO =
• <i>Cis-</i>Unsaturated Analogues of 3,8,13,18,23-Pentaazapentacosane (BE-4-4-4-4):  Synthesis and Growth Inhibitory Effects on Human Prostate Cancer Cell Lines
  作者：Venodhar K. Reddy、Aparajita Sarkar、Aldonia Valasinas、Laurence J. Marton、Hirak S. Basu、Benjamin Frydman

  DOI：10.1021/jm000310s

  日期：2001.2.1

  DU145, PC-3, and DuPro) using a MTT assay. LnCap and DU145 cells were very sensitive, PC-3 cells were relatively resistant, and DuPro cells were intermediate in sensitivity to most of these synthetic pentamines. In all cell lines, pentamines that had unsaturation(s) at the end of the chain showed the highest cell growth inhibitory effects. The cellular uptake, effects on cellular polyamine levels, and

  从我们以前对多胺-核酸相互作用的理化研究结果来看，我们得出的结论是，呈顺式构型的多胺类似物能够包裹双螺旋的主要凹槽，能够将天然多胺从其核酸结合位点移出，并具有抑制作用。细胞分裂。基于该假设，制备了九种不饱和五胺，其形式正式是由具有细胞毒性的五胺3,8,13,18,23-五aazapentacosane（BE-4-4-4-4）衍生而来，旨在提高抗肿瘤活性。将顺式双键引入到BE-4-4-4-4的饱和五氮杂五硼烷结构的所有可能位置中，以生成两个五碳杂酚，四个五碳二烯，两个五碳三烯和一个五碳四烯。顺式双键也应为混合功能氧化酶提供良好的靶标，该功能可以消除血清中不饱和五胺的积累，从而降低动物的全身毒性。我们使用MTT测定法确定了这些新的五胺在四种培养的人类前列腺癌细胞系（LnCap，DU145，PC-3和DuPro）中抑制生长的能力。LnCap和DU145细胞非常敏感，PC-3细胞具有相对抗性，而D