3-环戊氧-4-甲氧基苯甲醛 | 67387-76-2

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香醛(含缩醛,半缩醛)
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-环戊氧-4-甲氧基苯甲醛
• 中文别名: 3-(环戊基氧基)-4-甲氧基苯甲醛
• 英文名称: 3-cyclopentyloxy-4-methoxybenzylaldehyde
• 英文别名: 3-(cyclopentyloxy)-4-methoxybenzaldehyde；3-cyclopentyloxy-4-methoxybenzaldehyde
• CAS: 67387-76-2
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: FZFWPURYSWKIRT-UHFFFAOYSA-N

物化性质

• 熔点：
  107-110℃ (ethyl acetate )
• 沸点：
  124-126°C
• 密度：
  1.136±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 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：
  2912499000
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P270,P264,P280,P337+P313,P305+P351+P338,P302+P352,P332+P313,P362,P301+P310+P330,P405
• 危险品运输编号：
  2810
• 危险性描述：
  H301,H315,H319
• 储存条件：
  室温，惰性气氛

SDS

Name:	3-(Cyclopentyloxy)-4-methoxybenzaldehyde 97% Material Safety Data Sheet
Synonym:
CAS:	67387-76-2

Section 1 - Chemical Product MSDS Name:3-(Cyclopentyloxy)-4-methoxybenzaldehyde 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
67387-76-2	3-(Cyclopentyloxy)-4-methoxybenzaldehy	97%	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.
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 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.

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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.

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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# 67387-76-2: 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: Viscous liquid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 124 - 126 deg C @0mmHg
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: C13H16O3
Molecular Weight: 220.27

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, bases, acids.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 67387-76-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(Cyclopentyloxy)-4-methoxybenzaldehyde - 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# 67387-76-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 67387-76-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 67387-76-2 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：

  3-环戊氧-4-甲氧基苯甲醛 在 sodium chlorite 、 氯化亚砜 、 氨基磺酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.75h， 生成 吡拉米司特
  参考文献：
  名称：

  Selective Type IV Phosphodiesterase Inhibitors as Antiasthmatic Agents. The Syntheses and Biological Activities of 3-(Cyclopentyloxy)-4-methoxybenzamides and Analogs

  摘要：

  The syntheses and biological activities of a number of benzamide derivatives, designed from rolipram, which are selective inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), are described. The effects of changes to the alkoxy groups, amide linkage, and benzamide N-phenyl ring on the inhibition of the cytosolic PDE IV from pig aorta have been investigated. As a result, some highly potent and selective PDE IV inhibitors have been identified. The most potent compounds have been further evaluated for their inhibitory potencies against PDE IV obtained from and superoxide O-2(-) generation from guinea pig eosinophils in vitro. Selected compounds have also been examined for their activities in inhibiting histamine-induced bronchospasm in anaesthetized guinea pigs. 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide (15j) showed exceptional potency in all tests and may have therapeutic potential in the treatment of asthma.

  DOI：

  10.1021/jm00037a021
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-环戊氧-4-甲氧基苯甲醛
  参考文献：
  名称：

  Improving metabolic stability of phosphodiesterase-4 inhibitors containing a substituted catechol: prevention of reactive intermediate formation and covalent binding

  摘要：

  A detailed study directed towards metabolic stability optimization of the alkoxy substituents on the catechol moiety of CDP-840 is reported. Replacement of the methoxy and cyclopentyloxy substituents by cyclobutyloxy and/or difluromethoxy groups resulted in the discovery of potent and selective PDE4 inhibitors where the formation of reactive metabolites that could covalently bind to microsomal protein was significantly reduced or eliminated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00349-9

文献信息

• Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis
  作者：Jiguo Ma、Qinghai Zhou、Guanshui Song、Yongchang Song、Guoqing Zhao、Kuiling Ding、Baoguo Zhao

  DOI：10.1002/anie.202017306

  日期：2021.5.3

  Direct α‐functionalization of NH2‐free glycinates with relatively weak electrophiles such as α,β‐unsaturated esters still remains a big challenge in organic synthesis. With chiral pyridoxal 5 d as a carbonyl catalyst, direct asymmetric conjugated addition at the α‐C of glycinate 1 a with α,β‐unsaturated esters 2 has been successfully realized, to produce various chiral pyroglutamic acid esters 4 in 14–96 %

  用相对较弱的亲电试剂（例如，α，β-不饱和酯）将不含NH 2的甘氨酸直接进行α-官能化仍然是有机合成中的一大挑战。以手性吡ido醛5 d作为羰基催化剂，已成功实现在甘氨酸1a的α-C与α，β-不饱和酯2的直接不对称共轭加成反应，以14-96％的收率生产各种手性焦谷氨酸酯4原位内酰胺化后具有81–97％ee的物质。该反式与顺非对映异构体可以通过色谱法同时获得，并且可以很容易地通过叔丁基去除和随后的Barton转化为手性4取代的吡咯烷-2-酮，例如具有相同绝对构型的阿兹海默氏药物Rolipram（11）。脱羧。
• Oxime-carbamates and oxime-carbonates as bronchodilators and
  申请人：American Home Products Corporation

  公开号：US05124455A1

  公开（公告）日：1992-06-23

  There are disclosed compounds of the formula ##STR1## wherein R is ##STR2## R.sup.1 is hydrogen, lower alkyl or ##STR3## a is 1-3; b is 1-3; c is 0-2; X, Y and Z are each, independently, a bond, O, S. or NH, with the proviso that if one of X or Y is O, S or NH, the other must be a bond; R.sup.2 is amino, loweralkylamino, arylamino, loweralkoxy or aryloxy; R.sup.3 is hydrogen, halo, hydroxy, lower alkoxy, aryloxy, loweralkanoyloxy, amino, lower alkylamino, arylamino or loweralkanoylamino; R.sup.4 and R.sup.5 are each, independently hydrogen or lower alkyl; m is 0-4; n is 1-4; and o is 1-4; and, which by virtue of their ability to selectively inhibit an isoenzyme of 3':5'-cyclic AMP phosphodiesterase located in pulmonary smooth muscle tissue and inflammatory cells, are bronchodilatory and antinflammatory and so are useful in the treatment of acute and chronic bronchial asthma and associated pathologies.

  已公开的化合物的化学式为##STR1##其中R为##STR2##R.sup.1为氢、较低的烷基或##STR3##a为1-3；b为1-3；c为0-2；X、Y和Z分别独立地为键合、O、S或NH，但若X或Y中的一个为O、S或NH，则另一个必须为键合；R.sup.2为氨基、较低的烷基氨基、芳基氨基、较低的烷氧基或芳氧基；R.sup.3为氢、卤素、羟基、较低的烷氧基、芳氧基、较低的烷酰氧基、氨基、较低的烷基氨基、芳基氨基或较低的烷酰胺基；R.sup.4和R.sup.5分别独立地为氢或较低的烷基；m为0-4；n为1-4；o为1-4；由于它们具有选择性地抑制位于肺平滑肌组织和炎症细胞中的3':5'-环磷酸腺苷磷酸二酯酶的同工酶的能力，因此具有支气管扩张和抗炎作用，因此在治疗急性和慢性支气管哮喘及相关病理方面是有用的。
• Novel multitarget 5-arylidenehydantoins with arylpiperazinealkyl fragment: Pharmacological evaluation and investigation of cytotoxicity and metabolic stability
  作者：Anna Czopek、Adam Bucki、Marcin Kołaczkowski、Agnieszka Zagórska、Marcin Drop、Maciej Pawłowski、Agata Siwek、Monika Głuch-Lutwin、Elżbieta Pękala、Alicja Chrzanowska、Marta Struga、Anna Partyka、Anna Wesołowska

  DOI：10.1016/j.bmc.2019.07.046

  日期：2019.9

  affinity toward 5-HT1A and 5-HT7 receptors (Ki = 0.2–1.0 nM) but a negligible inhibitory effect on PDE4. The high affinity of the compounds for 5-HT1A and 5-HT7 receptors was further investigated by computer-aided studies. Moreover, compounds 13 and 18 showed no significant cytotoxicity in the MTT assay, but high clearance in the in vitro assay. In addition, these compounds behaved like 5-HT1A and 5-HT7

  根据5-羟色胺调节剂或药物（NAN-190，丁螺环酮，阿立哌唑）和磷酸二酯酶4（PDE4）抑制剂（咯利普兰，RO-20-1724）的结构，制备了一系列具有芳基哌嗪片段的新型多目标5-芳基乙内酰脲衍生物。合成的。在这些化合物中，5-（3,4-二甲氧基亚苄基-3-（4-（4-（2,3-二氯苯基）哌嗪-1-基）丁基）-咪唑烷-2,4-二酮（13）和5-发现（3-环戊氧基-4-甲氧基亚苄基-3-（4-（4-（2-甲氧基苯基）哌嗪-1-基）丁基）-咪唑烷-2,4-二酮（18）是最有前景的对5-HT 1A和5-HT 7受体（K i = 0.2–1.0 nM），但对PDE4的抑制作用可忽略不计。通过计算机辅助研究进一步研究了化合物对5-HT 1A和5-HT 7受体的高亲和力。而且，化合物13和18在MTT测定中没有显示出明显的细胞毒性，但是在体外测定中却具有很高的清除率。此外，在抑郁症动物模型中，这些化合物的行为类似于5-HT
• Compounds containing phenyl linked to aryl or heteroaryl by an
  申请人：Rhone-Poulenc Rorer Limited

  公开号：US05935978A1

  公开（公告）日：1999-08-10

  This invention is directed to the pharmaceutical use of phenyl compounds, which are linked to an aryl moiety by various linkages, for inhibiting tumor necrosis factor. The invention is also directed to the compounds, their preparation and pharmaceutical compositions containing these compounds. Furthermore, this invention is directed to the pharmaceutical use of the compounds for inhibiting cyclic AMP phosphodiesterase.

  这项发明涉及苯基化合物的药用，这些化合物通过各种连接与芳基团相连，用于抑制肿瘤坏死因子。该发明还涉及这些化合物、它们的制备以及含有这些化合物的药物组合物。此外，这项发明还涉及这些化合物的药用，用于抑制环磷酸腺苷磷酸二酯酶。
• Substituted phenethylsulfones and method of reducing TNF.alpha. levels
  申请人：Celgene Corporation

  公开号：US06011050A1

  公开（公告）日：2000-01-04

  Phenethylsulfones substituted in the position .alpha. to the phenyl group with a 1-oxoisoindoline or 1,3-dioxoisoindoline group reduce the levels of TNF.alpha. in a mammal. Typical embodiments are 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-aminoisoindoline- 1,3-dione and 2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-methylsulfonylethyl]isoindoline- 1,3-dione.

  α位取代苯基的苯乙基砜类化合物，带有1-氧代异吲哚啉基或1,3-二氧代异吲哚啉基，可以降低哺乳动物体内TNFα的水平。典型的实施例包括2-[1-(3-乙氧基-4-甲氧基苯基)-2-甲基砜基乙基]-4-氨基异吲哚啉-1,3-二酮和2-[1-(3-环戊氧基-4-甲氧基苯基)-2-甲基砜基乙基]异吲哚啉-1,3-二酮。