4-ethyl-4-hydroxycyclohexanone | 331475-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-ethyl-4-hydroxycyclohexanone
• 英文别名: 4-Ethyl-4-hydroxycyclohexan-1-one
• CAS: 331475-07-1
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: DTEDYTYLWQAGIX-UHFFFAOYSA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  239.7±33.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-ethyl-4-hydroxycyclohexanone 在 葡萄糖 Escherichia coli BL₂₁(DE₃)(pMM₄) whole cells 、 LB-Ampicillin medium 、 异丙基-beta-D-硫代半乳糖吡喃糖苷 作用下， 以 水 为溶剂， 以49%的产率得到5-(2-hydroxyethyl)-5-ethyldihydrofuran-2-one
  参考文献：
  名称：

  New Bioorganic Reagents:  Evolved Cyclohexanone MonooxygenaseWhy Is It More Selective?

  摘要：

  Four mutants of the cyclohexanone monooxygenase (CHMO) evolved as catalysts for Baeyer-Villiger oxidation of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified. The most important, however, is the finding that, in a number of cases, a mutant with a single exchange, Phe432Ser, was shown to be as robust and more selective as a catalyst than the wild-type CHMO. All biotransformations were performed on a laboratory scale, allowing full characterization of the products. The absolute configurations of two products were established. A model suggesting a possible role of the 432 serine residue in enantioselectivity control is proposed.

  DOI：

  10.1021/jo061349t
• 作为产物：
  描述：

  8-Ethyl-1,4-dioxa-spiro[4.5]decan-8-ol 在 盐酸 、 水 作用下， 以655 mg的产率得到4-ethyl-4-hydroxycyclohexanone
  参考文献：
  名称：

  转氨酶在疏水性底物生物胺化分散体系中的应用

  摘要：

  通过使用由低极性溶剂（例如异辛烷或甲基叔丁基醚），非离子表面活性剂和少量水组成的分散体系，可以实现疏水性底物具有挑战性的生物胺化作用。在这些条件下，胺转氨酶（ATA）被证明可以有效地进行各种取代的环己酮的还原胺化，与相应的化学还原胺化反应相比，可以提供良好的转化率，同时还具有出色的立体选择性。因此，通过生物催化合成，合成和表征了一系列有用的4-取代的氨基环己烷。

  DOI：

  10.1002/adsc.201901434

文献信息

• BRIDGED COMPOUNDS AS HIV INTEGRASE INHIBITORS
  申请人：Venkatraman Shankar

  公开号：US20120022045A1

  公开（公告）日：2012-01-26

  Compounds of Formula I are inhibitors of HIV integrase and inhibitors of HIV replication: the asterisk * in Q denotes the point of attachment to the rest of the compound; and n, L1, L2, X 1 , X 2 , χ 3 , Y, Z, R 1 , R 2 and R 3 are defined herein. The N compounds are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset or progression of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se (or as hydrates or solvates thereof) or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  化学式I的化合物是HIV整合酶的抑制剂和HIV复制的抑制剂：Q中的星号*表示与化合物其余部分的连接点；n，L1，L2，X1，X2，χ3，Y，Z，R1，R2和R3在此定义。N化合物用于预防或治疗HIV感染以及预防、治疗或延缓艾滋病的发病或进展。这些化合物可以作为化合物本身（或其水合物或溶剂化物）或作为药物学上可接受的盐的形式用于对抗HIV感染和艾滋病。这些化合物及其盐可作为药物组合物中的成分，可选地与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。
• Asymmetric Baeyer−Villiger Oxidations of 4-Mono- and 4,4-Disubstituted Cyclohexanones by Whole Cells of Engineered <i>Escherichia </i><i>c</i><i>oli</i>
  作者：Marko D. Mihovilovic、Gang Chen、Shaozhao Wang、Brian Kyte、Fernande Rochon、Margaret M. Kayser、Jon D. Stewart

  DOI：10.1021/jo001292p

  日期：2001.2.1

  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.
• Asymmetric microbial reduction of ketones: absolute configuration of trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol
  作者：Cristina Pinedo-Rivilla、Mariana Carrara Cafêu、Josefina Aleu Casatejada、Ângela Regina Araujo、Isidro G. Collado

  DOI：10.1016/j.tetasy.2009.11.001

  日期：2009.12

  A set of five fungal species, Botrytis cinerea, Trichoderma viride and Eutypa lata, and the endophytic fungi Colletotrichum crassipes and Xylaria sp., was used in screening for microbial biocatalysts to detect monooxygenase and alcohol dehydrogenase activities (for the stereoselective reduction of carbonyl compounds). 4-Ethylcyclohexanone and acetophenone were biotransformed by the fungal set. The main reaction pathways involved reduction and hydroxylations at several positions including tertiary carbons. B. cinerea was very effective in the bioreduction of both substrates leading to the chiral alcohol (S)-1-phenylethanol in up to 90% enantiomeric excess, and the cis-trans ratio for 4-ethylcyclohexanol was 0:100. trans-4-Ethyl-1-(1S-hydroxyethyl)cyclohexanol, obtained from biotransformation by means of an acyloin-type reaction, is reported here for the first time. The absolute configurations of the compounds trans-4-ethyl-1-(1S-hydroxyethyl)cyclohexanol and 4-(1S- and 4-(1R-hydroxyethyl)cyclohexanone were determined by NMR analysis of the corresponding Mosher's esters. (C) 2009 Elsevier Ltd. All rights reserved.
• THERAPIES WITH LANTHIONINE C-LIKE PROTEIN 2 LIGANDS AND CELLS PREPARED THEREWITH
  申请人：Landos Biopharma, Inc.

  公开号：US20190160100A1

  公开（公告）日：2019-05-30

  Provided are compounds that target the lanthionine synthetase C-like protein 2 pathway and cells, such as immune cells, prepared in vitro with the compounds. The compounds and cells can be used to treat a number of conditions, including infectious diseases, hyperproliferative disorders, inborn errors of metabolism, chronic immunometabolic diseases, autoimmune diseases, organ transplant rejection, inflammatory disorders, and chronic pain, among others.
• New Bioorganic Reagents:  Evolved Cyclohexanone MonooxygenaseWhy Is It More Selective?
  作者：Margaret M. Kayser、Christopher M. Clouthier

  DOI：10.1021/jo061349t

  日期：2006.10.1

  Four mutants of the cyclohexanone monooxygenase (CHMO) evolved as catalysts for Baeyer-Villiger oxidation of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified. The most important, however, is the finding that, in a number of cases, a mutant with a single exchange, Phe432Ser, was shown to be as robust and more selective as a catalyst than the wild-type CHMO. All biotransformations were performed on a laboratory scale, allowing full characterization of the products. The absolute configurations of two products were established. A model suggesting a possible role of the 432 serine residue in enantioselectivity control is proposed.