4-亚甲基环己烷羧酸乙酯 | 145576-28-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 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: 4-亚甲基环己烷羧酸乙酯
• 中文别名: 4-亚甲基亚乙基环己烷-1-甲酸乙酯
• 英文名称: ethyl 4-methylidenecyclohexanecarboxylate
• 英文别名: ethyl 4-methylenecyclohexanecarboxylate；ethyl 4-methylenecyclohexane-1-carboxylate；ethyl 4-methylenecyclohexylcarboxylate；ethyl 4-methylidenecyclohexane-1-carboxylate
• CAS: 145576-28-9
• 化学式: C₁₀H₁₆O₂
• mdl: MFCD12498694
• 分子量: 168.236
• InChiKey: DLVGFWIRQAUWDC-UHFFFAOYSA-N

物化性质

• 沸点：
  47°/0.7mm
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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
• 海关编码：
  2916209090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 4-methylidenecyclohexane-1-carboxylate
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: Ethyl 4-methylidenecyclohexane-1-carboxylate
CAS number: 145576-28-9

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H16O2
Molecular weight: 168.2

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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.

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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

反应信息

• 作为反应物：
  描述：

  4-亚甲基环己烷羧酸乙酯 在 吡啶 、 lithium aluminium tetrahydride 、 三正丁基氢锡 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 63.0h， 生成 1-甲基-4-亚甲基环己烷
  参考文献：
  名称：

  Synthesis of bridgehead-substituted bicyclo[2.2.1]heptanes by radical cyclization

  摘要：

  A kinetic investigation shows that the rate of cyclization (k(C)) of the (4-methylenecyclohexyl)methyl radical 3 at 25-degrees-C is 4.4 x 10(2) s-1, which is considerably slower than that (2.3 x 10(5) s-1) of the parent 5-hexenyl radical. The energy of activation for the process 3 - 4 is 12.8 kcal mol-1, which is in excellent agreement with theoretical values derived from force-field calculations. Ring-closure of appropriately substituted (4-methylenecyclohexyl)methyl radical precursors allows the synthesis of bicyclo[2.2.1]heptyl systems with useful functionality at the bridgehead to be achieved readily and in high yield. An interesting example is given of the application of an iodine-atom-transfer cyclization to the synthesis of a bicyclo[2.2.1]heptane functionalized at C7 and C1.

  DOI：

  10.1021/jo00060a029
• 作为产物：
  描述：

  对环己酮甲酸乙酯 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以66%的产率得到4-亚甲基环己烷羧酸乙酯
  参考文献：
  名称：

  WO2006/136245

  摘要：

  公开号：
• 作为试剂：
  描述：

  potassium tert-butylate 、 对环己酮甲酸乙酯 、 氯化铵 在 甲基三苯基溴化膦 ice 、 乙酸乙酯 、 magnesium sulfate 、 silica gel 、 hexane-diethyl ether 、 4-亚甲基环己烷羧酸乙酯 作用下， 以 乙醚 为溶剂， 反应 32.5h， 以7.1 g (66% of the theoretical amount) of the desired product 4-methylenecyclohexane carboxylic acid ethyl ester were obtained的产率得到4-亚甲基环己烷羧酸乙酯
  参考文献：
  名称：

  Substituted spiro-compounds and the use thereof for producing medicaments

  摘要：

  本发明涉及取代的螺环化合物、制备这些化合物的过程、包含这些化合物的药物以及使用这些化合物制备药物的用途。

  公开号：

  US07981883B2

文献信息

• [EN] FUSED TRICYCLIC INHIBITORS OF MAMMALIAN TARGET OF RAPAMYCIN<br/>[FR] INHIBITEURS TRICYCLIQUES CONDENSÉS DE MTOR (MAMMALIAN TARGET OF RAPAMYCIN)
  申请人：SCHERING CORP

  公开号：WO2012027234A1

  公开（公告）日：2012-03-01

  This invention relates to novel fused tricyclic compounds that are inhibitors of mammalian Target of Rapamycin (mTOR) kinase, which is also known as FRAP, RAFT, RAPT or SEP, and are useful in the treatment of cellular proliferative diseases, for example cancer and other proliferative disorders.

  这项发明涉及新颖的融合三环化合物，它们是哺乳动物雷帕霉素靶点（mTOR）激酶的抑制剂，也被称为FRAP、RAFT、RAPT或SEP，并且在治疗细胞增殖性疾病方面有用，例如癌症和其他增殖性障碍。
• Design, Synthesis, and Biological Evaluation of First-in-Class Dual Acting Histone Deacetylases (HDACs) and Phosphodiesterase 5 (PDE5) Inhibitors for the Treatment of Alzheimer’s Disease
  作者：Obdulia Rabal、Juan A. Sánchez-Arias、Mar Cuadrado-Tejedor、Irene de Miguel、Marta Pérez-González、Carolina García-Barroso、Ana Ugarte、Ander Estella-Hermoso de Mendoza、Elena Sáez、Maria Espelosin、Susana Ursua、Tan Haizhong、Wu Wei、Xu Musheng、Ana Garcia-Osta、Julen Oyarzabal

  DOI：10.1021/acs.jmedchem.6b00908

  日期：2016.10.13

  Simultaneous inhibition of phosphodiesterase 5 (PDE5) and histone deacetylases (HDAC) has recently been validated as a potentially novel therapeutic approach for Alzheimer’s disease (AD). To further extend this concept, we designed and synthesized the first chemical series of dual acting PDE5 and HDAC inhibitors, and we validated this systems therapeutics approach. Following the implementation of structure-

  磷酸二酯酶5（PDE5）和组蛋白脱乙酰基酶（HDAC）的同时抑制最近已被证实是阿尔茨海默氏病（AD）潜在的新型治疗方法。为了进一步扩展这个概念，我们设计并合成了第一个化学作用的双作用PDE5和HDAC抑制剂系列，并验证了该系统的治疗方法。在实施基于结构和知识的方法之后，设计了初始命中并显示了其来验证我们的双重体外抑制假说。然后，寻求优化策略以获得适合体内的工具化合物在AD模型中进行测试。最初的命中被翻译成具有适当细胞功能反应（组蛋白乙酰化和cAMP / cGMP反应元件结合（CREB）磷酸化在纳摩尔范围内），可接受的治疗窗（> 1 log单位）和穿越血液的能力的分子–脑屏障，从而将7鉴定为体内概念验证测试的候选者（Cuadrado-Tejedor，M。Garcia-Barroso，C .；JA，Sánchez-Arias；俄克拉荷马州拉巴尔；梅德罗斯（Mederos），S .；乌加特（A.）佛朗哥（Franco，R
• [EN] NOVEL PYRAZOLO[1,5-a]PYRROLO[3,2-e]PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS DE PYRAZOLO[1,5-A]PYRROLO[3,2-E]PYRIMIDINE UTILISÉS COMME INHBITEURS DE MTOR
  申请人：SCHERING CORP

  公开号：WO2012027239A1

  公开（公告）日：2012-03-01

  The present invention relates to certain pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine compounds of Formula (I) as inhibitors of mammalian Target of Rapamycin (mTOR) kinase, which is also known as FRAP, RAFT, RAPT or SEP. The compounds may be used in the treatment of cancer and other disorders where mTOR is deregulated. The present invention further provides pharmaceutical compositions comprising the pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine compounds.

  本发明涉及某些吡唑[1,5-a]吡咯[3,2-e]嘧啶化合物，其化学式为(I)，作为哺乳动物雷帕霉素靶点(mTOR)激酶的抑制剂，也被称为FRAP、RAFT、RAPT或SEP。这些化合物可用于治疗癌症和其他mTOR失调的疾病。本发明进一步提供了包含吡唑[1,5-a]吡咯[3,2-e]嘧啶化合物的药物组合物。
• Cobalt-Catalyzed Regioselective Olefin Isomerization Under Kinetic Control
  作者：Xufang Liu、Wei Zhang、Yujie Wang、Ze-Xin Zhang、Lei Jiao、Qiang Liu

  DOI：10.1021/jacs.8b01815

  日期：2018.6.6

  Olefin isomerization is a significant transformation in organic synthesis, which provides a convenient synthetic route for internal olefins and remote functionalization processes. The selectivity of an olefin isomerization process is often thermodynamically controlled. Thus, to achieve selectivity under kinetic control is very challenging. Herein, we report a novel cobalt-catalyzed regioselective olefin

  烯烃异构化是有机合成的重大转变，为内烯烃和远程功能化过程提供了一条便捷的合成路线。烯烃异构化过程的选择性通常受热力学控制。因此，在动力学控制下实现选择性是非常具有挑战性的。在此，我们报告了一种新型的钴催化区域选择性烯烃异构化反应。通过利用可微调的 NNP 钳配体结构，该催化系统具有区域选择性的高动力学控制。这种温和的催化系统能够以优异的产率和区域选择性将带有多种官能团的 1,1-二取代烯烃异构化。这种转化的合成效用通过高度选择性地制备用于全合成 minfiensine 的关键中间体得到了强调。此外，还开发了一种新策略，通过在双键的 γ 位上安装取代基来实现 1-烯烃到 2-烯烃的选择性单异构化。机理研究支持原位生成的 Co-H 物种经历了双键/β-H 消除序列的迁移插入以提供异构化产物。由于对β-H消除步骤的区域选择性的有效配体控制，在这种钴催化的烯烃异构化中总是优选受阻较小的烯烃产物。开发了一种新策略，通过在双键的
• [EN] COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS<br/>[FR] ASSOCIATIONS D'INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015005901A1

  公开（公告）日：2015-01-15

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组合物，以及抑制NS5A蛋白功能的方法。