4-(3,4-二氯苯基)-1-四氢萘酮 | 79560-19-3

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 4-(3,4-二氯苯基)-1-四氢萘酮
• 中文别名: 4-(3,4-二氯苯基)-3,4-二氢-(2H)萘酮；舍曲林中间体；4-(3,4-二氯苯)-3,4-二-2H-萘-1-酮；4-(3,4-二氯苯基)-3,4-二氢萘酮；4-(3,4-二氯苯基)-1-萘满酮；4-(3,4二氯苯基)-1-四氢萘酮；4-(3,4-氯苯基)-1-四氢萘酮
• 英文名称: 4-(3,4-dichlorophenyl)-1-tetralone
• 英文别名: 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone；4-(3,4-dichlorophenyl)tetralin-1-one；4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one；4-(3,4-dichlorophenyl)tetrahydronaphthalone；4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-one
• CAS: 79560-19-3
• 化学式: C₁₆H₁₂Cl₂O
• mdl: MFCD02093088
• 分子量: 291.177
• InChiKey: JGMBHJNMQVKDMW-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99°C
• 沸点：
  403.0±45.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 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
• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  -20°C 冰箱

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(3,4-Dichlorophenyl)-1-tetralone
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: 4-(3,4-Dichlorophenyl)-1-tetralone
CAS number: 79560-19-3

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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.

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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.

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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.

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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:

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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.

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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: C16H12Cl2O
Molecular weight: 291.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：白色或类白色的结晶性粉末。

用途： 4-(3,4-二氯苯基)-1-四氢萘酮可用作舍曲林中间体，用于合成抗抑郁剂等。它也用于合成盐酸舍曲林等抗抑郁药物。

生产方法： 由4-(3,4-二氯苯基)-3,4-二氢-1-(2H)-萘酮合成而得。

反应信息

• 作为反应物：
  描述：

  4-(3,4-二氯苯基)-1-四氢萘酮 在 gold(III) chloride 、 N,N-diethylaniline borane 、 sodium hydride 、 cesium fluoride 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 57.0h， 生成 舍曲林
  参考文献：
  名称：

  Catalytic Lewis and Brønsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes

  摘要：

  一系列含有α,β-二取代二胺和氨基醇基团的烷基和烯基对甲氧基苯被合成出来，这些化合物是从β-硝基和β-叠氮苄基醇在AuCl₃存在下作为催化剂的条件下合成的。基于机理考虑和依赖于A^1,3-烯基应变的过渡态模型，主要形成了同构二取代产物。这些产物可能在设计药用相关化合物和作为手性配体用于不对称催化方面具有实用价值。一种新的合成方法合成了（+）-去甲丙丁胺（Zoloft）。

  DOI：

  10.1139/cjc-2020-0016
• 作为产物：
  描述：

  3,4-二氯碘苯 在 bis(1,5-cyclooctadiene)nickel (0) 、 三氟甲磺酸 、 lithium chloride 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 17.08h， 生成 4-(3,4-二氯苯基)-1-四氢萘酮
  参考文献：
  名称：

  乙烯基芳烃的镍催化α-羰基烷基芳基化：方便地获得γ，γ-二芳基羰基和芳基四氢萘酮衍生物。

  摘要：

  我们报告了镍催化的乙烯基芳烃与α-卤代羰基化合物和芳基锌试剂的镍催化区域选择性α-羰基烷基芳基化。该反应适用于伯，仲和叔α-卤代羰基分子，以及电子化的芳基锌试剂。该反应产生具有α-仲，叔和季碳中心的γ，γ-二芳基羰基衍生物。该产品可以轻松转化为芳基四氢萘酮，包括抗抑郁药Zoloft的前体。

  DOI：

  10.1002/anie.201913435

文献信息

• α,α-Diarylethylene Glycols as Valuable Precursor for Synthesis of 1,1-Diarylethenes and α,α-Diaryl Acetaldehydes
  作者：Praveen Kumar Tiwari、Balasubramaniam Sivaraman、Indrapal Singh Aidhen

  DOI：10.1002/ejoc.201700467

  日期：2017.7.7

  Towards assembling of diarylmethine unit present in biologically important molecules, we have developed a new Weinreb Amide (WA) based building block, derived from glycolic acid. The WA functionality present in this building block had allowed the sequential addition of various arylmagnesium bromide reagents in a controlled manner enabling assembling of diarylmethine unit. The developed synthetic route

  为了组装生物学上重要的分子中存在的二芳基次甲基单元，我们开发了一种新的基于 Weinreb 酰胺 (WA) 的结构单元，该结构单元源自乙醇酸。该构件中存在的 WA 官能团允许以受控方式顺序添加各种芳基溴化镁试剂，从而能够组装二芳基次甲基单元。开发的合成路线可以轻松获得重要的二芳基乙烯和 α,α-二芳基乙二醇。合成的α,α-二芳基乙二醇为合成重要的对称和不对称α,α-二芳基乙醛作为有价值的中间体铺平了道路。
• Facile synthesis, characterization and pharmacological activities of 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 5,6-dihydro-3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles
  作者：N. Chidananda、Boja Poojary、V. Sumangala、N. Suchetha Kumari、Prashanth Shetty、T. Arulmoli

  DOI：10.1016/j.ejmech.2012.02.030

  日期：2012.5

  Two new series of compounds namely, 3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadizoles (5a–j) and 5,6-dihydro-3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadizoles (7a–j) were prepared. In continuation of a previously reported study, the first series (5a–j) were synthesized by the cyclocondensation of 4-amino-5-(2-bromo-5-methoxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (4) with various

  两个新的系列化合物，即3,6-二取代-1,2,4-三唑[3,4- b ] [1,3,4]噻二唑（5a – j）和5,6-二氢-3,6制备了-二取代-1,2,4-三唑并[3,4- b ] [1,3,4]噻二唑（7a – j）。在先前报道的研究基础上，第一个系列（5a – j）是通过4-氨基-5-（2-溴-5-甲氧基苯基）-2,4-二氢-3 H -1,2的环缩合反应合成的，（4-）三唑-3-硫酮（4）与氯氧磷中的各种取代的芳族羧酸和第二系列（7a – j）通过（4）的反应）在对甲苯磺酸存在下用各种取代的芳族醛 （4）与醛（9）的反应提供了用对甲苯磺酸处理的席夫碱（10）而不是环化产物（11）。通过光谱分析在结构上确认了合成的化合物，并研究了它们的抗炎，止痛，抗氧化和抗菌活性。一些测试化合物显示出显着的药理活性。
• Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: the counteranion and solvent effects, and substrate scope
  作者：Fei Chen、Ziyuan Ding、Yanmei He、Jie Qin、Tianli Wang、Qing-Hua Fan

  DOI：10.1016/j.tet.2012.03.019

  日期：2012.7

  Asymmetric hydrogenation of N-alkyl and N-aryl ketimines catalyzed by chiral cationic η6-arene-(N-monosulfonylated diamine) Ru(II) complexes has been investigated. Strong counteranion and solvent effects on the enantioselectivity were observed. The ruthenium catalyst bearing non-coordinating BArF− anion was found to be particularly effective for the hydrogenation of acyclic and exocyclic N-alkyl ketimines

  的不对称氢化ñ -烷基和Ñ通过催化芳基酮亚胺的手性阳离子η 6 -arene-（Ñ -monosulfonylated二胺）的Ru（II）络合物进行了研究。观察到强烈的抗衡阴离子和溶剂对对映选择性的影响。钌催化剂轴承非配位BARF -阴离子被认为是对无环和环外的氢化特别有效ñ -烷基酮亚胺在（BOC）的存在下2O在二氯甲烷中或什至在无溶剂条件下提供的手性胺，其ee可达99％以上，并具有完全转化率。或者，在不存在（Boc）2 O的情况下，具有手性磷酸根阴离子和相应磷酸作为添加剂的钌催化剂也有效用于N-烷基酮亚胺的氢化，对映选择性和完全转化率优异。对于Ñ -芳基酮亚胺降低通过使用钌催化剂轴承BARF观察对映体过量-阴离子。因此，该催化方案为光学活性胺提供了简便实用的途径，并已成功用于对映体纯的（+）-舍曲林的克级合成中。
• Asymmetric Hydrogenation of N-Alkyl Ketimines with Phosphine-Free, Chiral, Cationic Ru-MsDPEN Catalysts
  作者：Fei Chen、Tianli Wang、Yanmei He、Ziyuan Ding、Zhiwei Li、Lijin Xu、Qing-Hua Fan

  DOI：10.1002/chem.201002846

  日期：2011.1.24

  (Solvent) free and easy: A phosphine‐free, chiral, cationic Ru–MsDPEN complex [(S,S)‐1] is found to be an efficient catalyst for the enantioselective hydrogenation of a range of often‐problematic N‐alkyl ketimines (see scheme). This new method provides a more practical and greener synthetic approach to optically active amines, particularly N‐alkyl amines, such as Sertraline.

  （溶剂）易用：无膦，手性，阳离子的Ru-MsDPEN络合物[（S，S）-1 ]是有效的催化剂，用于对一系列经常有问题的N烷基酮亚胺进行对映选择性氢化（请参阅方案）。这种新方法为旋光性胺（尤其是N-烷基胺，如舍曲林）提供了一种更实用，更绿色的合成方法。
• [EN] TREATMENT OF CNS DISORDERS WITH TRANS 4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-1-NAPTHALENAMINE AND ITS FORMAMIDE<br/>[FR] TRAITEMENT DES TROUBLES DU SYSTEME NERVEUX CENTRAL AVEC DE LA TRANS 4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-1-NAPTHALENAMINE ET SON FORMAMIDE
  申请人：SEPRACOR INC

  公开号：WO2004024669A1

  公开（公告）日：2004-03-25

  Treatment of CNS disorders with (1R,4S)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine; and (1S,4R)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine is disclosed. A process for preparing 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine is also disclosed. The process includes the preparation of all four isomers of N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]formamide, which are also useful.

  用(1R,4S)-转式4-(3,4-二氯苯基)-1,2,3,4-四氢-1-萘胺；和(1S,4R)-转式4-(3,4-二氯苯基)-1,2,3,4-四氢-1-萘胺来治疗中枢神经系统疾病；并且揭示了制备4-(3,4-二氯苯基)-1,2,3,4-四氢-1-萘胺的方法。该方法包括制备N-[4-(3,4-二氯苯基)-1,2,3,4-四氢萘-1-基]甲酰胺的四个异构体，这些异构体也是有用的。