1-(2,3-二氯苯基)哌嗪 | 41202-77-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 哌嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(2,3-二氯苯基)哌嗪
• 中文别名: 1-(2,3-二氯苯基)哌嗪盐酸盐
• 英文名称: 1-(2,3-dichloro-phenyl)-piperazine
• 英文别名: 2,3-dichlorophenylpiperazine；4-(2,3-dichlorophenyl)piperazine；N-(2,3-dichlorophenyl)piperazine；1-(2,3-Dichlorophenyl)piperazine
• CAS: 41202-77-1
• 化学式: C₁₀H₁₂Cl₂N₂
• 分子量: 231.125
• InChiKey: UDQMXYJSNNCRAS-UHFFFAOYSA-N

物化性质

• 熔点：
  242-244°C
• 沸点：
  127°C/0.8mm
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

2,3-二氯苯基哌嗪是人用阿立哌唑的已知代谢物。

2,3-dichlorophenylpiperazine is a known human metabolite of aripiprazole.

来源:NORMAN Suspect List Exchange

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 1-(2,3-Dichlorophenyl)piperazine
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 1-(2,3-Dichlorophenyl)piperazine
CAS number: 41202-77-1

---

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.
Store in closed vessels.
Storage:

---

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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H12Cl2N2
Molecular weight: 231.1

---

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, hydrogen chloride.

---

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

制备方法与用途

DCPP is a potent inhibitor of DHCR7, the final enzyme in cholesterol biosynthesis.

反应信息

• 作为反应物：
  描述：

  1-(2,3-二氯苯基)哌嗪 在 氯化亚砜 、 氢气 、 C₃₀H₃₄N₄*BF₄^(1-)*Rh⁽¹⁺⁾*C₈H₁₂ 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 60.0~150.0 ℃ 、8.0 MPa 条件下， 反应 26.5h， 生成 阿立哌唑
  参考文献：
  名称：

  配位组装使烯烃的高选择性催化氢氨甲基化成为可能

  摘要：

  烯烃的加氢氨甲基化 (HAM) 是生产胺类最有前途和最实用的方法之一，但控制线性和支化产物之间的选择性仍然具有挑战性。在此，发现一系列通过配位组装制备的固体主链 NHC-铑 ( I ) 聚合物是烯烃 HAM 中的高效单中心催化剂。观察到生产率（高达 98% 的收率）和线性选择性（高达 99:1）的显着提高，这主要是由于固体催化剂的扩展配位组装结构所施加的限制。除了广泛的底物范围外，创纪录的营业额为 2.1 × 10 5实现了，固体催化剂可以重复使用18次以上，活性和选择性没有明显损失。该协议对敏感官能团具有很高的容忍度，其实用性体现在直接从烯丙醇或杂环胺合成几种领先的药物，无需任何保护或脱保护操作，规模可达一克。

  DOI：

  10.1039/d2gc04195b
• 作为产物：
  描述：

  1-(2,3-二氯苯基)哌嗪 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 1-(2,3-二氯苯基)哌嗪
  参考文献：
  名称：

  WO2008/34628

  摘要：

  公开号：
• 作为试剂：
  描述：

  6-(4-chlorobutoxy)indan-1-one 、 1-(2,3-二氯苯基)哌嗪 在 1-(2,3-二氯苯基)哌嗪 作用下， 生成 6-[4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butoxy]-indan-1-one
  参考文献：
  名称：

  [EN] NOVEL INTERMEDIATES USEFUL FOR THE PREPARATION OF ARIPIPRAZOLE AND METHODS FOR THE PREPARATION OF THE NOVEL INTERMEDIATES AND ARIPIPRAZOLE
  [FR] NOUVEAUX INTERMEDIAIRES UTILES POUR LA PREPARATION DE L'ARIPIPRAZOLE ET PROCEDES DE PREPARATION DE CES NOUVEAUX INTERMEDIAIRES ET DE L'ARIPIPRAZOLE

  摘要：

  本申请所披露的发明涉及一种改进的阿立哌唑（1）制备工艺，其包括：（i）在碱和溶剂存在下，以90至110摄氏度的温度反应6-羟基-1-茚酮（11）和1,4-二卤丁烷（12），以形成新型中间体6-（4-卤丁氧基）-茚-1-酮（3），（ii）将新型中间体与1-（2,3-二氯苯基）-哌嗪（9）反应，得到另一种新型中间体6- [4- [4-（2,3-二氯苯基）-1-哌嗪基] -氧基] -茚-1-酮（2），以及（iii）将所得的新型化合物与叠氮化钠反应。该发明还涉及公式（2）和（3）的新型中间体及其制备工艺。

  公开号：

  WO2006038220A1

文献信息

• [EN] NOVEL AGENTS TARGETING CYP51<br/>[FR] NOUVEAUX AGENTS CIBLANT CYP51
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2015048306A1

  公开（公告）日：2015-04-02

  The invention provides inhibitors of a sterol C14-demethylase, a new series of 4- aminopyridyl-based lead inhibitors targeting Trypanosoma cruzi CYP51 (TcCYP51) developed using structure-based drug design as well as structure -property relationship (SPR) analyses. The screening hit starting point, LP 10 (KD < 42 nM; EC50 of 0.65 μΜ), has been optimized to give the potential leads that have low nanomolar binding affinity to TcCYP51 and significant activity against T. cruzi amastigotes cultured in human myoblasts. Many of the optimized compounds have improved microsome stability, and most are selective against the T. cruzi CYP51 relative to human CYPs 1A2, 2D6 and 3A4 (<50% inhibition at 1 μΜ). A rationale for the improvement of microsome stability and selectivity of inhibitors against human metabolic CYP enzymes is presented. In addition, the binding mode of several compounds of the invention with the T. brucei CYP51 (TbCYP51) ortholog has been characterized by x-ray structure analysis. Orally active compounds and their cyclodextrin complexes have been shown to be effective against Chagas-infected mice.

  该发明提供了一种甾醇C14-去甲基酶的抑制剂，这是一种新系列基于4-氨基吡啶的首选抑制剂，通过基于结构的药物设计以及结构-性质关系（SPR）分析来瞄准Trypanosoma cruzi CYP51（TcCYP51）而开发的。筛选起始点LP 10（KD < 42 nM；EC50为0.65 μΜ）已经经过优化，产生了具有低纳摩尔级别结合亲和力和对在人类肌细胞培养的T. cruzi游离体的显著活性的潜在首选抑制剂。许多经过优化的化合物具有改善的微粒体稳定性，大多数相对于人类CYPs 1A2、2D6和3A4对T. cruzi CYP51具有选择性（在1 μΜ下<50%的抑制）。提出了改善微粒体稳定性和抑制剂对人类代谢CYP酶的选择性的理由。此外，通过X射线结构分析表征了该发明的几种化合物与T. brucei CYP51（TbCYP51）同源物的结合方式。口服活性化合物及其环糊精复合物已被证明对克氏病感染的小鼠有效。
• Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
  申请人：——

  公开号：US20040157849A1

  公开（公告）日：2004-08-12

  Compounds of formula (I) 1 are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.

  式（I）的化合物是新颖的VR1拮抗剂，可用于治疗疼痛、炎症性热性过敏、尿失禁和膀胱过度活动。
• Pd-Catalyzed Synthesis of Piperazine Scaffolds Under Aerobic and Solvent-Free Conditions
  作者：Sean W. Reilly、Robert H. Mach

  DOI：10.1021/acs.orglett.6b02591

  日期：2016.10.21

  A facile Pd-catalyzed methodology providing an efficient synthetic route to biologically relevant arylpiperazines under aerobic conditions is reported. Electron donating and sterically hindered aryl chlorides were aminated to afford yields up to 97%, with examples using piperazine as solvent, illustrating an ecofriendly, cost-effective synthesis of these privileged structures.

  据报道，一种简便的钯催化方法为有氧条件下生物相关的芳基哌嗪提供了有效的合成路线。给电子和位阻芳基氯化物被胺化，产率高达 97%，其中使用哌嗪作为溶剂的例子，说明了这些特殊结构的生态友好、经济有效的合成。
• Chrysin-piperazine conjugates as antioxidant and anticancer agents
  作者：Rahul V. Patel、Bhupendra Mistry、Riyaz Syed、Anuj K. Rathi、Yoo-Jung Lee、Jung-Suk Sung、Han-Seung Shinf、Young-Soo Keum

  DOI：10.1016/j.ejps.2016.02.011

  日期：2016.6

  bone marrow derived mesenchymal stem cells (hBM-MSCs). Overall, 7a-w indicated remarkable antioxidant power in scavenging DPPH· and ABTS·+, particularly analogs 7f, 7j, 7k, 7l, 7n, 7q, 7v, 7w have shown promising free radical scavenging activity. Analogs 7j and 7o are identified to be highly active candidates against HeLa and CaSki cell lines, whereas 7h and 7l along with 7j proved to be very sensitive

  用1,4-二溴丁烷合成7-（4-溴丁氧基）-5-羟基-2-苯基-4H-铬-4-酮中间体处理ry素促进了ry素与多种哌嗪基团的结合，这些via嗪基团通过反应而装备在二甘醇单甲醚溶剂中用双（2-氯乙基）胺盐酸盐制得相应的胺。除了使用SRB分析评估宫颈癌癌细胞系（HeLa和CaSki）和卵巢癌细胞系SK-OV-3的体外抗癌功效外，还通过DPPH和ABTS生物测定法对制成品的自由基清除潜力进行了体外分析。 。可接受的7a-w毒性使用Madin-Darby犬肾（MDCK）细胞系进行检查。另外，使用人骨髓来源的间充质干细胞（hBM-MSC）检查了所提供化合物的细胞毒性性质。总的来说，7a-w显示出清除DPPH ·和ABTS ·+的显着抗氧化能力，尤其是类似物7f，7j，7k，7l，7n，7q，7v，7w具有清除自由基的活性。已确定类似物7j和7o是针对HeLa和CaSki细胞系的高活性候选物，而7h和
• Design, synthesis and biological activity of new amides derived from 3-methyl-3-phenyl-2,5-dioxo-pyrrolidin-1-yl-acetic acid
  作者：Jolanta Obniska、Anna Rapacz、Sabina Rybka、Beata Powroźnik、Elżbieta Pękala、Barbara Filipek、Paweł Żmudzki、Krzysztof Kamiński

  DOI：10.1016/j.ejmech.2015.07.017

  日期：2015.9

  A series of new 3-methyl-3-phenyl-2,5-dioxo-pyrrolidin-1-yl-acetamides (6–23) has been synthesized and evaluated for their anticonvulsant activity in the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizure tests after intraperitoneal injection in mice. The acute neurological toxicity was determined using the rotarod test. The in vivo preliminary pharmacological results showed

  合成了一系列新的3-甲基-3-苯基-2,5-二氧代吡咯烷-1-基乙酰胺（6 – 23），并评估了它们在最大电击（MES）和皮下戊四氮（皮下）中的抗惊厥活性。SC PTZ）在小鼠腹膜内注射后癫痫发作的测试。使用旋转脚踏试验确定急性神经毒性。的体内初步药理结果表明，在整个系列只有两种化合物（15，21）是没有活性的，而其它分子在癫痫（MES或/和至少一个动物模型显示保护SC PTZ）。在体内在小鼠中进行的定量研究表明，在MES测试中，活性最高的是1- 2- [4-（2-甲氧基苯基）-哌嗪-1-基] -2-氧代乙基} -3-甲基-3-苯基-吡咯烷-2,5-二酮（17），1- 2- [4-（4-氟苯基）-哌嗪-1-基] -2-氧代乙基} -3-甲基-3-苯基-吡咯烷-2 ，ED 5值分别为97.51 mg / kg（17），104.11 mg / kg（8）和114.68 mg / kg（7）的1