反式-4-乙基环己烷羰基氯化物 | 67589-87-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: 反式-4-乙基环己烷羰基氯化物
• 中文别名: 反式-4-乙基环己基甲酰氯
• 英文名称: 4-Ethyl-cyclohexancarbonsaeurechlorid
• 英文别名: 4-ethylcyclohexanecarbonyl chloride；trans-4-ethylcyclohexylcarbonylchloride；4-ethyl-cyclohexancarbonyl chloride；4-ethylcyclohexane-1-carbonyl chloride
• CAS: 67589-87-1；77477-82-8
• 化学式: C₉H₁₅ClO
• 分子量: 174.671
• InChiKey: OBDHUMSKEKYCKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  反式-4-乙基环己烷羰基氯化物 在 thiazolium salt 、 三乙胺 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 生成 1-(4-Ethyl-cyclohexyl)-heptane-1,4-dione
  参考文献：
  名称：

  Burrow, Michael P.; Gray, George W.; Lacey, David, Zeitschrift fur Chemie, 1986, vol. 26, # 1, p. 21 - 23

  摘要：

  DOI：
• 作为产物：
  描述：

  对乙基苯甲酸 在 platinum(IV) oxide 氯化亚砜 、 氢气 作用下， 以 溶剂黄146 为溶剂， 25.0 ℃ 、5.07 MPa 条件下， 反应 9.0h， 生成 反式-4-乙基环己烷羰基氯化物
  参考文献：
  名称：

  降血脂药的研究。三，ω-环烷基-2-氧代烷基芳烃磺酸盐的合成及其酯酶抑制活性。

  摘要：

  多种ω-环烷基-2-氧代烷基芳磺酸酯被合成，并评估了其酯酶和胰凝乳蛋白酶抑制活性以及降血脂活性。在测试的化合物中，具有烷基链末端环己基取代的2-氧代烷基芳磺酸酯（4、8和13）表现出显著的酯酶抑制活性，而4和8中的几种化合物还显示出强大的降血脂作用。本文讨论了这些化合物的结构-活性关系。

  DOI：

  10.1248/cpb.35.2426

文献信息

• Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB₂ Cannabinoid Receptor Activity
  作者：Jennifer M. Frost、Michael J. Dart、Karin R. Tietje、Tiffany R. Garrison、George K. Grayson、Anthony V. Daza、Odile F. El-Kouhen、Betty B. Yao、Gin C. Hsieh、Madhavi Pai、Chang Z. Zhu、Prasant Chandran、Michael D. Meyer

  DOI：10.1021/jm901214q

  日期：2010.1.14

  affinity CB2 agonists (5, 16). Substitution at the N1-indole position was then examined. A series of aminoalkylindoles was prepared and several substituted aminoethyl derivatives were active (23−27, 5) at the CB2 receptor. A study of N1 nonaromatic side chain variants provided potent agonists at the CB2 receptor (16, 35−41, 44−47, 49−54, and 57−58). Several polar side chains (alcohols, oxazolidinone) were

  已经制备了几种对CB 2大麻素受体具有高亲和力并且对CB 1受体具有选择性的3-酰基环吲哚。各种3-酰基取代基进行了调查，和四甲基环组被发现导致高亲和力CB 2激动剂（5，16）。然后检查在N1-吲哚位置的取代。（A系列aminoalkylindoles的制备和几个取代氨基乙基衍生物是活性23 - 27，5在CB）2受体。N1非芳香族侧链变异体的研究为CB 2受体提供了有效的激动剂（16，35 - 41，44 - 47，49 - 54，和57 - 58）。几个极性侧链（醇类，恶唑烷酮）的良好的耐受性为CB 2受体的活性（41，50），而其他（酰胺，酸）导致较弱的或无活性的化合物（55和56）。N1芳香族侧链还提供几个高亲和力CB 2受体激动剂（61，63，65，和69），但是在体外CB一般不太有效的2个功能测定法均高于非芳香族侧链类似物。
• Synthesis, Photo-sensitive and Electrochemical Properties of Rod-like Aromatic Aldehyde with Azo Bridge
  作者：Minyan Zheng、Yongsheng Wei、Wei Geng

  DOI：10.1515/chem-2015-0122

  日期：2015.12.31

  Eight new rod-like liquid crystal molecules composed by a long rigid core of three six-member rings (cyclohexane ring or benzene ring), azo, ester and terminal aldehyde groups have been prepared. These rod-like liquid crystalline molecules were designed to construct new structures to further study photo-isomerization in their mesophases. All the compounds have been characterized based on their basic spectral data, differential scanning calorimeter (DSC) and hot stage polarizing optical microscope (HS-POM). The result showed that all the molecules, even those with the shortest terminal methyl group, have liquid crystalline properties. Their mesophases are nematic within the temperature ranges from 85 to 145°C. They exhibit photo-sensitivities not only in methanol solutions but also in a mesophase when exposed to UV light. The highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) and the differences between the frontier molecular orbitals (E_g) of these compounds were determined by cyclic voltammetry. The effect of even-odd carbon number of the terminal straight alkyl chain on the UV spectral data and the E_g were observed. The difference between the E_g of these compounds are in excellent agreement with the difference of their maximum absorption wavelength in UV spectra.

  已经制备了八种新的棒状液晶分子，它们由三个六元环（环己烷环或苯环）的长刚性核心、偶氮基、酯基和末端醛基团组成。这些棒状液晶分子被设计用来构建新的结构，以进一步研究它们在中介相中的光异构化。所有化合物都根据它们的基本光谱数据、差示扫描量热计（DSC）和热台偏光显微镜（HS-POM）进行了表征。结果显示，所有分子，即使是那些末端甲基最短的分子，都具有液晶性质。它们的中间相在85至145°C的温度范围内为向列相。它们不仅在甲醇溶液中而且在中介相中对紫外线表现出光敏感性。这些化合物的最高占有轨道（HOMO）、最低未占有轨道（LUMO）以及前沿分子轨道之间的差异（E_g）通过循环伏安法确定。观察到了末端直链烷基偶数-奇数碳数对UV光谱数据和E_g的影响。这些化合物的E_g差异与它们UV光谱中最大吸收波长的差异非常一致。

• Studies on hypolipidemic agents. III. Synthesis and esterase-inhibitory activity of .OMEGA.-cycloalkyl-2-oxoalkyl arenesulfonates.
  作者：KAZUO OGAWA、TADAFUMI TERADA、YOSHIYUKI MURANAKA、TOSHIHIRO HAMAKAWA、SETSURO FUJII

  DOI：10.1248/cpb.35.2426

  日期：——

  Various ω-cycloalkyl-2-oxoalkyl arenesulfonates were synthesized and evaluated for esterase-and chymotrypsin-inhibitory activities and hypolipidemic activity. Among the tested compounds, 2-oxoalkyl arenesulfonates (4, 8 and 13) having a cyclohexyl substituent at the terminus of the alkyl chain exhibited considerable esterase-inhibitory activity, and several compounds among 4 and 8 also exhibited potent hypolipidemic action. The structure-activity relationships of these compounds are discussed.

  多种ω-环烷基-2-氧代烷基芳磺酸酯被合成，并评估了其酯酶和胰凝乳蛋白酶抑制活性以及降血脂活性。在测试的化合物中，具有烷基链末端环己基取代的2-氧代烷基芳磺酸酯（4、8和13）表现出显著的酯酶抑制活性，而4和8中的几种化合物还显示出强大的降血脂作用。本文讨论了这些化合物的结构-活性关系。
• Design, synthesis and structure-activity relationship studies of novel 4,4-bis(trifluoromethyl)imidazolines as acyl-CoA: Cholesterol acyltransferase (ACAT) inhibitors and antihypercholesterolemic agents
  作者：Hui-Yin Li、Indawati DeLucca、George A. Boswell、Jeffrey T. Billheimer、Spencer Drummond、Peter J. Gillies、Candy Robinson

  DOI：10.1016/s0968-0896(97)00058-8

  日期：1997.7

  Novel 4,4-bis(trifluoromethyl)imidazolines have been found to be the potent acyl-CoA cholesterol acyltransferase (ACAT) inhibitors. ACAT is responsible for cholesterol esterification in the intestine, liver, and the arterial wall. These novel imidazolines also inhibit cholesterol ester formation in the macrophage. Several compounds have shown potent serum cholesterol-lowering activity in several animal

  已经发现新型的4，4-双（三氟甲基）咪唑啉是有效的酰基-CoA胆固醇酰基转移酶（ACAT）抑制剂。ACAT负责肠，肝和动脉壁中的胆固醇酯化。这些新型咪唑啉还抑制巨噬细胞中胆固醇酯的形成。几种化合物在几种动物模型中均显示出有效的降低血清胆固醇的活性。2-苯基的对位取代对于体外和体内活性至关重要。具有2-苯基上的对氰基和4-烷基环己基酰胺作为侧链的5-位的4,4-双（三氟甲基）咪唑啉在该系列中具有最有效的抑制活性。基于生化研究，该系列在胆固醇与酶的结合方面起着竞争性抑制剂的作用，这与迄今为止发现的大多数ACAT抑制剂不同。初步的生物学研究得到X射线晶体结构，分子模型和结构-活性关系（SAR）研究的支持，表明该系列可能是胆固醇的模拟物。
• Studies on hypolipidemic agents. IV. Syntheses and biological activities of trans- and cis-2-(4-alkylcyclohexyl)-2-oxoethyl arenesulfonates.
  作者：KAZUO OGAWA、TADAFUMI TERADA、YOSHIYUKI MURANAKA、TOSHIHIRO HAMAKAWA、SHUNSAKU OHTA、MASAO OKAMOTO、SETSURO FUJII

  DOI：10.1248/cpb.35.3276

  日期：——

  trans-and cis-2-Diazo-1- (4-alkylcyclohexyl) -1-ethanones were reacted with arenesulfonic acids to afford the corresponding 2- (4-alkylcyclohexyl) -2-oxoethyl arenesulfonates. The esteraseinhibitory activity and hypolipidemic effect of the arenesulfonates were examined, and it was found that in most cases, the trans-isomers were more active than the corresponding cis-isomers. Stereoselective syntheses of several biologically potent trans-isomers (trans-3) were also developed.

  trans-和cis-2-二氮-1-(4-烷基环己基)-1-乙酮与芳烃磺酸反应，得到相应的2-(4-烷基环己基)-2-氧代乙基芳烃磺酸酯。对这些芳烃磺酸酯的酯酶抑制活性和降脂效果进行了研究，结果发现大多数情况下，trans-异构体的活性高于相应的cis-异构体。同时，还开发了几种生物活性强的trans-异构体（trans-3）的立体选择性合成方法。