(3-氧代环己基)乙酸酯 | 53164-77-5

• 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: (3-氧代环己基)乙酸酯
• 英文名称: 3-oxocyclohexyl acetate
• 英文别名: 3-acetoxycyclohexanone；3-acetoxy-cyclohexanone；3-Acetoxy-cyclohexanon；(3-oxocyclohexyl) acetate
• CAS: 53164-77-5
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: SHBSJXDUJMMRFE-UHFFFAOYSA-N

物化性质

• 沸点：
  230.8±33.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  cyclohexan-1,3-diol monoacetate 在 chromium(VI) oxide 、 溶剂黄146 、 苯 作用下， 生成 (3-氧代环己基)乙酸酯
  参考文献：
  名称：

  Dimroth; Resin, Chemische Berichte, 1942, vol. 75, p. 322,324

  摘要：

  DOI：

文献信息

• On the Michael Addition of Water to α,β-Unsaturated Ketones Using Amino Acids
  作者：Verena Resch、Christiane Seidler、Bi-Shuang Chen、Ian Degeling、Ulf Hanefeld

  DOI：10.1002/ejoc.201301230

  日期：2013.12

  The use of water as a nucleophile for Michael additions is still a challenge in organic chemistry. In this report we describe the use of amino acids as catalysts for the Michael addition of water to ?,?-unsaturated ketones. All 20 proteinogenic amino acids were screened and L-lysine was identified as the best candidate. To obtain a better insight and to determine the minimum requirements of the catalyst

  使用水作为迈克尔加成的亲核试剂仍然是有机化学中的一个挑战。在本报告中，我们描述了使用氨基酸作为将水与 α,β-不饱和酮进行迈克尔加成反应的催化剂。筛选了所有 20 种蛋白氨基酸，L-赖氨酸被确定为最佳候选者。为了更好地了解并确定催化剂的最低要求，测试了几种结构相关的化合物。在条件和平衡方面表征反应。
• Enantioselective Michael Addition of Water
  作者：Bi-Shuang Chen、Verena Resch、Linda G. Otten、Ulf Hanefeld

  DOI：10.1002/chem.201405579

  日期：2015.2.9

  enantioselective Michael addition using water as both nucleophile and solvent has to date proved beyond the ability of synthetic chemists. Herein, the direct, enantioselective Michael addition of water in water to prepare important β‐hydroxy carbonyl compounds using whole cells of Rhodococcus strains is described. Good yields and excellent enantioselectivities were achieved with this method. Deuterium

  迄今为止，已证明使用水作为亲核试剂和溶剂的对映选择性迈克尔加成超出了合成化学家的能力。在此，描述了使用红球菌菌株的全细胞，在水中直接、对映选择性迈克尔加成水来制备重要的β-羟基羰基化合物。该方法获得了良好的产率和优异的对映选择性。氘标记研究表明迈克尔水合酶仅通过反立体化学催化水的添加。
• An Unexpected Oxidation of Unactivated Methylene C–H Using DIB/TBHP Protocol
  作者：Yi Zhao、Wai-Leung Yim、Chong Kiat Tan、Ying-Yeung Yeung

  DOI：10.1021/ol2016466

  日期：2011.8.19

  An in situ generated hypervalent iodine species, bis(tert-butylperoxy)iodobenzene, was used as a peroxy radical source for the oxidation of unreactive, remote, and isolated alkyl (cyclic or aliphatic) esters and amides to the corresponding keto compounds under very mild conditions.

  原位生成的高价碘物质双（叔丁基过氧）碘苯用作过氧自由基源，可在非常温和的条件下将未反应的，较远且分离的烷基（环状或脂肪族）酯和酰胺氧化为相应的酮化合物情况。
• 15-oxosteroid compound and process for producing the same
  申请人：ASKA Pharmaceutical Co., Ltd.

  公开号：US10815268B2

  公开（公告）日：2020-10-27

  Provided is a process for producing a compound, which has an oxo group specifically introduced on the 15-position of a steroid skeleton and which is useful as an intermediate, with a high yield without complicated steps. A compound represented by the formula (2) is allowed to react with an oxidant (e.g., a hypervalent iodine compound) and a co-oxidant (e.g., a peroxide) to produce a 15-oxosteroid compound represented by the formula (1), which is useful as an intermediate: wherein R1 to R3 are the same or different and each represent a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, or a haloalkoxy group, R4 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acyl group, or an alkoxycarbonyl group, R5 represents a hydrogen atom, an alkyl group, or an acyl group, R6 represents a hydrogen atom, an alkyl group, an acyl group, or a sulfonyl group, X represents an oxygen atom (O) or a methylene group (CH2).

  本发明提供了一种化合物的生产工艺，该化合物在甾体骨架的 15 位上特别引入了一个氧代基团，可用作中间体，产量高，无需复杂步骤。让式 (2) 所代表的化合物与氧化剂（如高价碘化合物）和助氧化剂（如过氧化物）反应，生成式 (1) 所代表的 15-氧甾体化合物，该化合物可用作中间体： 其中 R1 至 R3 相同或不同，各自代表卤素原子、烷基、卤代烷基、烷氧基或卤代烷氧基，R4 代表氢原子、卤素原子、烷基、烷氧基、酰基、R5 代表氢原子、烷基或酰基，R6 代表氢原子、烷基、酰基或磺酰基，X 代表氧原子 (O) 或亚甲基 (CH2)。
• Kinetic resolution of 3-hydroxycyclohexanone using different lipases
  作者：Sanjib Kumar Karmee、Remco van Oosten、Ulf Hanefeld

  DOI：10.1016/j.tetasy.2011.09.011

  日期：2011.10

  A new approach to enantiomerically enriched cyclic beta-hydroxy ketones was developed. 3-Hydroxycyclohexanone was successfully resolved using lipase catalyzed transesterification. Among the lipases screened PFL, PCL, and PPL-II gave 57%, 39%, and 25% yield of the (R)-3-oxocyclohexyl acetate with 52%, 75%, and 91% ee. The PPL-II gave the highest E-value (32). The absolute configuration of the product was determined by comparison with the literature data. (C) 2011 Elsevier Ltd. All rights reserved.