2-(1-金刚烷基)乙酸甲酯 | 27174-71-6

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(1-金刚烷基)乙酸甲酯
• 中文别名: 1-金刚烷乙酸甲酯
• 英文名称: methyl (1-adamantyl)acetate
• 英文别名: methyl 2-(adamantan-1-yl)acetate；methyl 1-adamantaneacetate；Methyl 2-(1-adamantyl)acetate
• CAS: 27174-71-6
• 化学式: C₁₃H₂₀O₂
• mdl: MFCD01073581
• 分子量: 208.301
• InChiKey: MZIVXJGBKLZCKF-UHFFFAOYSA-N

物化性质

• 沸点：
  86 °C
• 密度：
  1.086±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  105.8±9.7℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.923
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2916209090

SDS

Name:	Methyl 2-(1-adamantyl)acetate 97% Material Safety Data Sheet
Synonym:
CAS:	27174-71-6

Section 1 - Chemical Product MSDS Name:Methyl 2-(1-adamantyl)acetate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
27174-71-6	Methyl 2-(1-adamantyl)acetate	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 27174-71-6: 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: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 86 deg C @0.3mmHg
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: C13H20O2
Molecular Weight: 208

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 27174-71-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 2-(1-adamantyl)acetate - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 27174-71-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 27174-71-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 27174-71-6 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：

  2-(1-金刚烷基)乙酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到1-金刚烷乙醇
  参考文献：
  名称：

  金刚烷基侧链作为染料敏化太阳能电池染料中的抗聚集部分

  摘要：

  报道了两种新型三芳胺染料，它们在 π 间隔基 ( BSH-2 ) 和供体 ( BSH-3 )上用乙基金刚烷基侧链修饰。乙基金刚烷基改性染料显示出比未改性参考染料 ( JK-305 ) 更高的光电压。用金刚烷基修饰的供体染料 ( BSH-3 ) 和抗聚集添加剂 CDCA制备的 DSSC 器件显示出该系列中最好的 PCE，为 6.1%。

  DOI：

  10.1002/chem.202201726
• 作为产物：
  描述：

  methyl bromo(3-bromo-1-adamantyl)acetate 以5%的产率得到
  参考文献：
  名称：

  KRASUTSKIJ, T. A.;CHESSKAYA, N. S.;RODIONOV, V. N.;BAULA, O. P.;YURCHENKO+, ZH. ORGAN. XIMII, 1985, 21, N 8, 1677-1684

  摘要：

  DOI：

文献信息

• Biologically active polycycloalkanes. 1. Antiviral adamantane derivatives
  作者：Koji Aigami、Yoshiaki Inamoto、Naotake Takaishi、Kenichi Hattori、Akira Takatsuki、Gakuzo Tamura

  DOI：10.1021/jm00241a015

  日期：1975.7

  acids and 1,3-adamantanediacetic acid (11). Some adamantylpyrimidines (24) and -purines (25 and 26) were also prepared. Antiviral activities of the compounds obtained in this work and a series of new 1-adamantyl alkyl ketones synthesized before, together with those of some known adamantane derivatives, were tested in vitro on monolayer culture of chick ambryo fibroblasts against Newcastle disease virus

  描述了合成1-取代的3-金刚烷基氯化物和溴化物（2），1-金刚烷基苯酚和-甲酚（3），1-金刚烷酸（6）以及1,3-金刚烷二乙酸（11）的简便方法。从这些关键中间体合成了几种新颖的衍生物：由金刚烷基酚（3）和酯（7、12和22），酰胺（13和18），硫代酰胺（9和16）形成的金刚烷基环己醇（4）和-环己酮（5）。 ，1-金刚烷羧酸（19）和-乙酸（6）酸，1,3-金刚烷二乙酸（11）中的am，（10），腈（15）和胺（14和17）。还制备了一些金刚烷嘧啶（24）和-嘌呤（25和26）。在这项工作中获得的化合物以及之前合成的一系列新的1-金刚烷基烷基酮以及某些已知的金刚烷衍生物的抗病毒活性，
• SUBSTITUTED PYRAZOLOPYRIMIDINES AND METHOD OF USE
  申请人：AbbVie Deutschland GmbH & Co. KG

  公开号：US20160304527A1

  公开（公告）日：2016-10-20

  Compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , R 4 , L 1 and G 1 are as defined in the specification, are useful in treating conditions or disorders prevented by or ameliorated by positive allosteric modulation of the γ-aminobutyric acid B (GABA-B) receptor. Methods for making the compounds are described. Also described are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.

  具有化学式(I)及其药用可接受的盐的化合物，其中R1、R2、R3、R4、L1和G1如规范中定义的那样，对于治疗由γ-氨基丁酸B（GABA-B）受体的正向变构调节预防或改善的症状或疾病是有用的。描述了制备这些化合物的方法。还描述了具有化学式(I)的化合物的药物组合物，以及使用这些化合物和组合物的方法。
• Conjugatively Stabilized Bridgehead Olefins:  Formation and Reaction of Remarkably Stable Homoadamant-3-enes Substituted with Phenyl and Methoxycarbonyl Groups
  作者：Masatomi Ohno、Motohiro Itoh、Masami Umeda、Ryoji Furuta、Kazumoto Kondo、Shoji Eguchi

  DOI：10.1021/ja953977q

  日期：1996.1.1

  Conjugatively stabilized double bonds were formed at the bridgehead of homoadamantane by way of the 1,2-carbon shift of adamantylcarbene (-carbenoid) intermediates generated from decomposition of the diazo precursors (1-adamantyl)diazophenylmethane (7) and methyl (1-adamantyl)diazoacetate (10). Decomposition to 4-phenyl- and 4-methoxycarbonyl-substituted homoadamant-3-enes 1 and 2 was much more efficient

  通过重氮前体 (1-金刚烷基) 重氮苯基甲烷 (7) 和甲基 (1-金刚烷基) 分解产生的金刚烷基卡宾 (-carbenoid) 中间体的 1,2- 碳位移，在高金刚烷的桥头处形成了共轭稳定的双键。 )重氮乙酸酯 (10)。在二氯甲烷中用 Rh2(OAc)4 催化分解为 4-苯基-和 4-甲氧基羰基取代的高金刚烷-3-烯 1 和 2 比光解或热解（FVP；在 7 的情况下，茚满-稠合高金刚烷是通过苯基卡宾重排然后插入桥连亚甲基产生的）。在 Rh 催化中，7 和 10 在己烷中和与 Rh2(NHCOCH3)4 的反应没有促进 1 和 2 的形成，这表明 Rh-卡宾配合物的极化结构参与了 1,2-碳位移。
• [EN] DERIVATIVES OF 4-(2-AMINO-1 -HYDROXYETHYL)PHENOL AS AGONISTS OF THE ß2 ADRENERGIC RECEPTOR<br/>[FR] DÉRIVÉS DE 4-(2-AMINO-1-HYDROXYÉTHYL)PHÉNOL COMME AGONISTES DU RÉCEPTEUR ?2-ADRÉNERGIQUE
  申请人：ALMIRALL LAB

  公开号：WO2009068177A1

  公开（公告）日：2009-06-04

  The present invention provides a compound of formula (I): wherein: • R1 is a group selected from -CH2OH,-NH(CO)H and • R2 is a hydrogen atom; or • R1 together with R2 form the group -NH-C(O)-CH=CH-, wherein the nitrogen atom is bound to the carbon atom in the phenyl ring holding R1 and the carbon atom is bound to the carbon atom in the phenyl ring holding R2 • R3a and R3b are independently selected from the group consisting of hydrogen atoms and C1-4alkyl groups, • n represents an integer from 1 to 3; • Ad represents 1-adamantyl or 2-adamantyl group, or a pharmaceutically-acceptable salt or solvate or stereoisomer thereof.

  本发明提供了一种化合物，其化学式为（I）：其中： • R1是从-CH2OH，-NH（CO）H中选择的基团； • R2是氢原子；或者 • R1与R2共同形成基团-NH-C（O）-CH=CH-，其中氮原子与持有R1的苯环中的碳原子结合，碳原子与持有R2的苯环中的碳原子结合； • R3a和R3b分别从氢原子和C1-4烷基基团组成的基团中独立选择； • n表示一个从1到3的整数； • Ad代表1-金刚烷基或2-金刚烷基基团，或其药学上可接受的盐、溶剂化合物或立体异构体。
• Azepine derivatives and use thereof
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US05658923A1

  公开（公告）日：1997-08-19

  An azepine compound of the formula ##STR1## wherein R is (a) ##STR2## in which R.sup.1 is hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, or optionally substituted phenyl, and n is 0 or 1, (b) cycloalkyl of C.sub.5-8 which is optionally substituted by lower alkyl, (c) norbornyl, (d) bicyclo[3.3.1]nonyl, (e) naphthyl, (f) 1,3-benzoxolyl, (g) pyridyl, or (h) thienyl, m is an integer of 0-4, and C* is an asymmetric carbon, and nontoxic salts thereof, processes for producing the same, and therapeutic agents containing the same as the active ingredient for treating diseases related to .sigma.-receptor. The compound (1) and nontoxic salts thereof have a high affinity for .sigma.-receptor but scarcely any affinity for other receptors, thus being utilized for treating diseases related to .sigma.-receptor, such as schizophrenia.

  一种azepine化合物，其化学式为##STR1##其中R为(a) ##STR2##其中R.sup.1为氢、较低烷基、较低烷氧基、羟基、卤素，或者可选择地取代苯基，n为0或1，(b) C.sub.5-8的环烷基，可选择地取代为较低烷基，(c) 诺邦基，(d) 双环[3.3.1]壬基，(e) 萘基，(f) 1,3-苯并噁唑基，(g) 吡啶基，或(h) 噻吩基，m为0-4的整数，C*为不对称碳，以及其无毒盐，制备该化合物的方法，以及包含该化合物作为活性成分的治疗剂，用于治疗与σ-受体相关的疾病。该化合物(1)及其无毒盐对σ-受体具有高亲和力，但几乎不与其他受体结合，因此可用于治疗与σ-受体相关的疾病，如精神分裂症。