4-ethyl-4-methylcyclohexanone | 35155-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-ethyl-4-methylcyclohexanone
• 英文别名: 4-ethyl-4-methylcyclohexan-1-one
• CAS: 35155-49-8
• 化学式: C₉H₁₆O
• mdl: MFCD17013056
• 分子量: 140.225
• InChiKey: MABKONZEVCZGAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  95-98 °C(Press: 16 Torr)
• 密度：
  0.882±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  4-ethyl-4-methylcyclohexanone 在 sulfur tetrafluoride 作用下， 生成 1,1-Difluor-4-methyl-4-ethyl-cyclohexan
  参考文献：
  名称：

  核磁共振光谱。取代的 1,1-二氟环己烷的构象特性

  摘要：

  带有各种取代基的墒-氟环己烷的环反转率和构象平衡通过氟磁共振光谱测定。对于 1,1-二氟环己烷, 1,1,2,2-四氟环己烷, 4-甲基-4-乙基-1,1-二氟环己烷4e,,4-二甲基-1,1-二氟环己烷, 和 4-氯-1,l -二氟环己烷，发现用于环反转的活化能 (E,) 落在 8.0 和 11.2 kcal/mol 之间。对于 4-氯-1,1-二氟环己烷，发现在丙烯和丙酮溶液中，赤道氯构象和氯轴构象的自由能差异分别为 -0.32 和 -0.17 kcal/mol，并且几乎与温度无关。4-甲基-4-乙基-1,1-二氟环己烷的构象对应的自由能差为 - 0。10 大卡/摩尔。对于 3-甲基-、4-甲基-和 4-叔丁基-取代的 11-二氟环己烷，构象之间的平衡发生了很大的变化，有利于一种构象异构体，因此只能从氟磁共振光谱中得出定性结论。

  DOI：

  10.1021/ja00977a018
• 作为产物：
  描述：

  2-甲基丁醛 在 5percent Pd/C 硫酸 、 氢气 作用下， 以 乙酸乙酯 、 苯 为溶剂， 生成 4-ethyl-4-methylcyclohexanone
  参考文献：
  名称：

  Asymmetric Baeyer−Villiger Oxidations of 4-Mono- and 4,4-Disubstituted Cyclohexanones by Whole Cells of Engineered Escherichia coli

  摘要：

  Whole cells of an Escherichia coli strain that overexpresses Acinetobacter sp. NCIB 9871 cyclohexanone monooxygenase have been used for the Baeyer-Villiger oxidations of a variety of 4-mono- and 4,4-disubstituted cyclohexanones. In cases where comparisons were possible, this new biocatalytic reagent provided lactones with chemical yields and optical purities that were comparable to those obtained from the purified enzyme or a strain of bakers' yeast that expresses the same enzyme. The efficient production of cyclohexanone monooxygenase in the E. coli expression system (ca. 30% of total soluble protein) allowed these oxidations to reach completion in approximately half the time required for the engineered bakers' yeast strain. Surprisingly, 4,4-disubstituted cyclohexanones were also accepted by the enzyme, and the enantioselectivities of these oxidations could be rationalized by considering the conformational energies of bound substrates along with the enzyme's intrinsic enantioselectivity. The enzyme expressed in E. coli cells also oxidized several 4-substituted cyclohexanones bearing polar substituents, often with high enantioselectivities. In the case of 4-iodocyclohexanone the lactone was obtained in > 98% ee and its absolute configuration was assigned by X-ray crystallography. The crystal belongs to the monoclinic P2(1) space group with a = 5.7400(10), b = 6.1650(10), c = 11.377(2) Angstrom, b = 99.98(2)degrees, and Z = 2. Taken together, these results demonstrate the utility of an engineered bacterial strain in delivering useful chiral building blocks in an experimentally simple manner.

  DOI：

  10.1021/jo001292p

文献信息

• Investigating<i>Saccharomyces cerevisiae</i>alkene reductase OYE 3 by substrate profiling, X-ray crystallography and computational methods
  作者：Robert W. Powell, III、M. Pilar Buteler、Sunidhi Lenka、Michele Crotti、Sara Santangelo、Matthew J. Burg、Steven Bruner、Elisabetta Brenna、Adrian E. Roitberg、Jon D. Stewart

  DOI：10.1039/c8cy00440d

  日期：——

  X-ray crystal structures of unliganded and phenol-bound OYE 3 were solved to 1.8 and 1.9 Å resolution, respectively. Both structures were nearly identical to that of OYE 1, with only a single amino acid difference in the active site region (Ser 296 versus Phe 296, part of loop 6). Despite their essentially identical static X-ray structures, molecular dynamics (MD) simulations revealed that loop 6 conformations

  酿酒酵母OYE 3与经过充分研究的巴斯德酵母OYE 1具有80％的序列同一性；而酿酒酵母OYE 3具有80％的序列同一性。然而，野生型OYE 3对某些烯烃底物表现出不同的立体选择性。在OYE 3中对Trp 116进行位点饱和诱变，然后进行底物谱分析表明，该突变的影响相对较小，与以前在OYE 1中观察到的相反。未配体和与酚结合的OYE 3的X射线晶体结构解析为1.8和1.9Å分辨率。两种结构都几乎与OYE 1相同，在活性位点区域只有一个氨基酸差异（Ser 296对Phe 296，循环6的一部分）。尽管它们具有基本相同的静态X射线结构，但分子动力学（MD）模拟显示，在OYE 3和OYE 1之间的溶液中，环6构象存在显着差异。在OYE 3中，环6保持与晶体结构中观察到的几乎一样的开放状态。相比之下，回路6在OYE 1的活性位点上闭合了约5％。4Å。与OYE 3相比，闭环闭合可能会为与OYE 1结
• [EN] PYRAZOLE CARBOXAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS PYRAZOLE CARBOXAMIDES, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014023258A1

  公开（公告）日：2014-02-13

  Provided herein are compounds of formula (AA): N N H HN O N N R R 6 A (R a ) p, (AA) stereoisomers or a pharmaceutically acceptable salt thereof, wherein A, R a, p, R and R 6 are defined herein, compositions including the compounds and methods of manufacturing and using the compounds for the treatment of diseases.

  本文提供了以下式（AA）的化合物：N N H HN O N N R R 6 A（R a）p，（AA）立体异构体或其药学上可接受的盐，其中A、R a、p、R和R 6在此处有定义，包括这些化合物的组合物以及用于治疗疾病的制备和使用这些化合物的方法。
• [EN] OXYSTEROLS AND METHODS OF USE THEREOF<br/>[FR] OXYSTÉROLS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2018075699A1

  公开（公告）日：2018-04-26

  Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R2, R3, R4, R5, and and R6 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

  根据公式（I）提供化合物及其药学上可接受的盐，以及药物组合物；其中R2、R3、R4、R5和R6的定义如本文所述。本发明的化合物被认为对预防和治疗各种疾病条件有用。
• [EN] CYCLAMEN ODORANT<br/>[FR] SUBSTANCE ODORANTE DE TYPE CYCLAMEN
  申请人：FIRMENICH & CIE

  公开号：WO2019015974A1

  公开（公告）日：2019-01-24

  The present invention concerns compounds of formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein each R1, independently from each other, represents a hydrogen atom or a methyl group; R2 and R3 represent, independently from each other, a C1-2 linear alkyl group or a C3-5 linear or branched alkyl group; R2 and R3, when taken together, represent a C2-5 linear, branched alkanediyl and one dotted line represents a carbon-carbon single bond and the second one a carbon-carbon double bond. The use of compound of formula (I) as perfuming ingredient of the floral type and the invention's compound as part of a perfuming composition or of a perfumed consumer product are also part of the present invention.

  本发明涉及式(I)的化合物，其形式可以是其立体异构体之一或其混合物，其中每个R1，彼此独立地代表氢原子或甲基基团；R2和R3彼此独立地代表C1-2直链烷基基团或C3-5直链或支链烷基基团；当R2和R3一起取时，它们代表C2-5直链、支链烷二基，并且一个点线代表碳-碳单键，第二个点线代表碳-碳双键。将式(I)的化合物用作花香型香料成分以及发明的化合物作为香料组合物或香水消费产品的一部分也属于本发明。
• Stereoselective Desymmetrizations by Recombinant Whole Cells Expressing the Baeyer–Villiger Monooxygenase fromXanthobacter sp. ZL5: A New Biocatalyst Accepting Structurally Demanding Substrates
  作者：Daniela V. Rial、Dario A. Bianchi、Petra Kapitanova、Alenka Lengar、Jan B. van Beilen、Marko D. Mihovilovic

  DOI：10.1002/ejoc.200700872

  日期：2008.3

  Baeyer–Villiger monooxygenase from Xanthobacter sp. ZL5 with respect to biotransformations of prochiral substrates is characterized. This enzyme catalyzes the desymmetrization of cyclic ketones bearing different chemical features with stereoselectivity similar to that obtained with a related protein fromAcinetobacter as a prototype representative of the cyclohexanone monooxygenase enzyme cluster. Moreover

  在这项工作中，过表达来自黄杆菌属的 Baeyer-Villiger 单加氧酶的工程全细胞的底物谱和立体选择性。ZL5 关于前手性底物的生物转化的特征。该酶催化具有不同化学特征的环酮的去对称化，立体选择性类似于用来自不动杆菌的相关蛋白质作为环己酮单加氧酶酶簇的原型代表获得的。此外，这种生物催化剂能够以优异的对映选择性转化以前没有被其他酶转化的空间要求高的底物。这些结果扩展了全细胞生物转化过程可获得的光学纯内酯的所有成分，它们是合成天然和生物活性产品的有用中间体。此外，我们观察到由该单加氧酶催化的非活化 C=C 键发生显着的环氧化反应。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）