(1R,3S)-2,2-二甲基-3-(2-氧代丙基)-环丙烷乙酸甲酯 | 54878-01-2

• 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: (1R,3S)-2,2-二甲基-3-(2-氧代丙基)-环丙烷乙酸甲酯
• 中文别名: (1R,3S)-2,2-二甲基-3-(2-丙酰)-环丙乙酸甲酯
• 英文名称: methyl 2,2-dimethyl-3-(2-oxopropyl)-1,3-Z-cyclopropylacetate
• 英文别名: methyl (1R)-cis(-)-2,2-dimethyl-3-(2-oxopropyl)cyclopropylacetate；methyl (1R,3S)-2,2-dimethyl-3-(2-oxopropyl)-cyclopropanacetate；methyl (1R,3S)-2,2-dimethyl-3-(2-oxopropyl)cyclopropaneacetate；2,2-dimethyl-3-(2-oxopropyl)-cis-cyclopropane-1-acetic acid methyl ester；cis-1.1-Dimethyl-2-methoxycarbonylmethyl-3-(2-oxo-propyl)-cyclopropan；methyl [(1R,3S)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]acetate；methyl [2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]acetate；methyl 1S,6R-3-oxo-3,4-secocaran-4-oate；methyl 2-[(1R,3S)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]acetate
• CAS: 54878-01-2
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: MGHKLYIYPFGGDY-DTWKUNHWSA-N

物化性质

• 沸点：
  104-106°C/3mmHg
• 密度：
  0.989±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	Methyl (1R 3S)-2 2-Dimethyl-3-(2-Oxopropyl )-Cyclopropaneacetate 96% Material Safety Data Sheet
Synonym:	None Known
CAS:	54878-01-2

Section 1 - Chemical Product MSDS Name:Methyl (1R 3S)-2 2-Dimethyl-3-(2-Oxopropyl )-Cyclopropaneacetate 96% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
54878-01-2	Methyl (1R,3S)-2,2-Dimethyl-3-(2-Oxopr	96%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
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.
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:

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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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.)

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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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 54878-01-2: 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 minimize contact with skin.
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: clear brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 104 - 106C @ 3.00mmHg
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: insoluble
Specific Gravity/Density:
Molecular Formula: C11H18O3
Molecular Weight: 198.26

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 54878-01-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl (1R,3S)-2,2-Dimethyl-3-(2-Oxopropyl )-Cyclopropaneacetate - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 54878-01-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 54878-01-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 54878-01-2 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：

  (1R,3S)-2,2-二甲基-3-(2-氧代丙基)-环丙烷乙酸甲酯 在 吡啶 、 氯化亚砜 、 盐酸羟胺 、 sodium methylate 、 sodium acetate 作用下， 以 甲醇 、 苯 为溶剂， 反应 28.25h， 生成 (1R,2R,6S,8R)-6-chloro-3,9,9-trimethyl-5-oxa-4-azatricyclo<6.1.0.0^2,6>non-3-ene
  参考文献：
  名称：

  Synthesis of new chiral heterocycles of the pyrazole and 2-isoxazoline types from (+)-3-carene.

  摘要：

  Preparation of chiral heterocyclic compounds of the pyrazole and 2-isoxazoline types starting from natural monoterpene hydrocarbon (+)-3-carene is described. Stereochemical assignment of the compounds synthesized is made by NMR spectroscopy and X-ray analysis together with the data obtained by molecular mechanics and quantum chemical calculations.

  DOI：

  10.1016/s0957-4166(00)86220-5
• 作为产物：
  描述：

  (+)-3-蒈烯 在 水 、 氧气 、 臭氧 、 盐酸氨基脲 作用下， 以 甲醇 为溶剂， 以65%的产率得到(1R,3S)-2,2-二甲基-3-(2-氧代丙基)-环丙烷乙酸甲酯
  参考文献：
  名称：

  在水存在下过氧化物烯烃臭氧分解产物在甲醇中的转化

  摘要：

  在水为助溶剂的条件下，研究了羟胺和氨基脲盐酸盐在甲醇中臭氧作用下，在双键上具有不同取代度的各种烯烃的臭氧分解的过氧化物产物的转化。

  DOI：

  10.1134/s1070428013100023

文献信息

• Novel S1P₁ Receptor Agonists – Part 1: From Pyrazoles to Thiophenes
  作者：Martin H. Bolli、Claus Müller、Boris Mathys、Stefan Abele、Magdalena Birker、Roberto Bravo、Daniel Bur、Patrick Hess、Christopher Kohl、David Lehmann、Oliver Nayler、Markus Rey、Solange Meyer、Michael Scherz、Gunther Schmidt、Beat Steiner、Alexander Treiber、Jörg Velker、Thomas Weller

  DOI：10.1021/jm4014373

  日期：2013.12.12

  identification of novel S1P1 receptor agonists, the pyrazole derivative 2 emerged as a hit structure. Medicinal chemistry efforts focused not only on improving the potency of the compound but in particular also on resolving its inherent instability issue. This led to the discovery of novel bicyclo[3.1.0]hexane fused thiophene derivatives. Compounds with high affinity and selectivity for S1P1 efficiently reducing

  通过旨在鉴定新型S1P 1受体激动剂的高通量筛选活动，吡唑衍生物2成为一种命中结构。药物化学工作不仅着重于提高化合物的效力，而且特别着重于解决其固有的不稳定性问题。这导致了新的双环[3.1.0]己烷稠合噻吩衍生物的发现。鉴定出对S1P 1具有高亲和力和选择性的化合物，可有效减少大鼠的淋巴细胞计数。例如，化合物85在S1P 1和S1P 3上的EC 50值为7和2880 nM。分别在大鼠和狗中具有良好的药代动力学特性，很好地分布在脑组织中，并且有效且剂量依赖性地降低了大鼠的淋巴细胞计数。自发性高血压大鼠口服给药后，S1P 1选择性化合物85仅对动物的苏醒阶段没有表现出对平均动脉压的影响，并且仅影响心率。
• Synthesis of Isonicotinic and Salicylic Acids Derivatives from (–)-α-Pinene and (+)-Δ3-Carene
  作者：Yu. V. Myasoedova、E. R. Nurieva、L. R. Garifullina、G. Yu. Ishmuratov

  DOI：10.1134/s1070363220110031

  日期：2020.11

  Optically active cyclobutanediyl- and cyclopropanediylbisalkylidene dihydrazides of isonicotinic and salicylic acids were synthesized when the peroxide products of ozonolysis of (–)-α-pinene and (+)-Δ3-carene were reduced with isonicotinic and salicylic acid hydrazides in methanol, methylene chloride or tetrahydrofuran. Using QSAR models, high antituberculosis activity in combination with low values

  当 (-)-α-蒎烯和 (+)-Δ3-蒎烯的臭氧分解过氧化物产物在甲醇、二氯甲烷或四氢呋喃。使用 QSAR 模型，预测得到的化合物具有高抗结核活性以及低急性毒性和最小抑制浓度。
• Concise Synthesis of Non-Protein Amino Acid from Natural Product via Schmidt Reaction
  作者：Kamila Gajcy、Tadeusz Librowski、Stanislaw Lochynski

  DOI：10.2174/157017809787893037

  日期：2009.4.1

  In this work we aimed at finding a concise method for the design of the new pharmacologically active compound 6, which is a precursor to obtaining non-protein amino acid 7 considered as GABA analogue, furthermore it can be used to construct enantiopure, conformationally restricted peptides. For this purpose the Schmidt reaction was applied.

  在这项工作中，我们的目标是找到一种简便的方法来设计具有药理活性的新化合物 6，它是获得被视为 GABA 类似物的非蛋白氨基酸 7 的前体，此外，它还可用于构建对映体纯的、构象受限的多肽。为此，我们采用了施密特反应。
• (+)-Trans-chrysanthemic acid from (+)-Δ3-carene
  作者：R. Sobti、Sukh Dev

  DOI：10.1016/s0040-4020(01)97467-8

  日期：1974.1

  A new and more efficient route for the conversion of the readily available (+)-Δ3-carene into (+)-trans-chrysanthemic acid is described.

  为容易获得的转化新的和更有效的路由（+） - Δ 3 -carene成（+） -反式-chrysanthemic酸进行说明。
• Transformations of peroxide ozonolysis products of natural olefins by N-containing organic compounds in methanol
  作者：G. Yu. Ishmuratov、Yu. V. Legostaeva、L. P. Botsman、M. P. Yakovleva、O. O. Shakhanova、R. R. Muslukhov、G. A. Tolstikov

  DOI：10.1007/s10600-009-9354-6

  日期：2009.5

  Transformations of peroxide ozonolysis products of cyclic and acyclic natural olefins with different degrees of saturation by hydroxylamine and semicarbazide hydrochlorides were investigated.

  研究了羟胺和氨基脲盐酸盐对不同饱和度环状和非环状天然烯烃的过氧化物臭氧分解产物的转化。