3,5,7-trimethyloxepan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,5,7-trimethyloxepan-2-one
• 英文别名: (3R,5S,7S)-3,5,7-trimethyloxepan-2-one
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: OHQXGQOPQUNBQI-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5,7-trimethyloxepan-2-one 在 sodium hydroxide 、 sodium dihydrogenphosphate 、 guinea-pig liver esterase 作用下， 以39%的产率得到(3S,5R,7R)-3,5,7-trimethyloxepan-2-one
  参考文献：
  名称：

  不动杆菌环己酮单加氧酶Baeyer-Villiger氧化合成天然产物前体

  摘要：

  通过酶促 Baeyer-Villiger 氧化法合成天然产物前体 U rich Schwarz-Linek,1a,a Andreas Krödel,a Friedrich-Alexander Ludwig,a Alexander Schulze,a Sebastian Rissom,b Udo Kragl,1b,b Vladimir I. Tishkov,c Marina Vogel*aa Leipzig University, Department of Chemistry and Mineralogy, Johannisalle 29, 04103 Leipzig, Germany 传真 [phone]；电子邮箱：[e-mail] b 德国于利希研究中心生物技术研究所 c 罗蒙诺索夫莫斯科国立大学化学酶学系，119899

  DOI：

  10.1055/s-2001-13394
• 作为产物：
  描述：

  (2R,4r,6S)-2,4,6-trimethylcyclohexanone 在 间氯过氧苯甲酸 作用下， 生成 3,5,7-trimethyloxepan-2-one
  参考文献：
  名称：

  4,6,8,10,16-Penta- and 4,6,8,10,16,18-Hexamethyldocosanes from the Cane Beetle Antitrogus parvulus - Cuticular Hydrocarbons with Unprecedented Structure and Stereochemistry

  摘要：

  [GRAPHICS]The major cuticular hydrocarbons from the cane beetle species Antitrogus parvulus were deduced to be 4,6,8,10,16,18-hexa- and 4,6,8,10,16-pentamethyldocosanes 2 and 3, respectively. Isomers of 2,4,6,8-tetramethylundecanal 27, 36, and 37, derived from 2,4,6-trimethylphenol, were coupled with the phosphoranes 28 and 29 to furnish alkenes and, by reduction, diastereomers of 2 and 3. Chromatographic and spectroscopic comparisons confirmed 2 as either 6a or 6b and 3 as either 34a or 34b.

  DOI：

  10.1021/ol0361453

文献信息

• Synthesis of the decalin core of codinaeopsin via an intramolecular Diels–Alder reaction
  作者：Mani Ramanathan、Chun-Jui Tan、Wen-Jung Chang、Hui-Hsu Gavin Tsai、Duen-Ren Hou

  DOI：10.1039/c3ob40480c

  日期：——

  the synthesis of the decalin core of codinaeopsin (1), a tryptophan-polyketide hybrid natural product with promising antimalarial activity (IC50 4.7 μM, against Plasmodium falciparum), via an intramolecular Diels–Alder (IMDA) reaction. A convergent synthesis was developed to prepare the precursors for the IMDA reaction in 10 steps. The exo cycloadducts were derived from thermal, IMDA reactions of the

  我们通过分子内Diels-Alder（IMDA）反应描述了codinaeopsin（1）的十氢化萘核心的合成，codinaeopsin（1）是一种色氨酸-聚酮化合物杂合天然产物，具有良好的抗疟活性（IC 50 4.7μM ，对抗恶性疟原虫）。进行了收敛合成，以十个步骤制备用于IMDA反应的前体。所述外切cycloadducts从含有Weinreb酰胺或酯共轭亲双烯体的基板的热，IMDA反应衍生的内切加合物是来自路易斯酸促进了基材的反应与甲酰基。无论外型和内IMDA的产物仅通过NMR光谱进行分离和表征。用X射线晶体学进一步证实了一个内环加合物。理论计算揭示了十氢化萘核心的取代基对IMDA工艺的影响。
• Conformation Induction Between Neighboring Dimethylpentane Segments
  作者：Reinhard W. Hoffmann、Richard Göttlich、Ulrich Schopfer

  DOI：10.1002/1099-0690(200105)2001:10<1865::aid-ejoc1865>3.0.co;2-e

  日期：2001.5

  A 2,4-dimethylpentane unit can be rendered monoconformational by the presence of a conformation-inducing group (an inductor group) at C-1 (cf. 6). The resulting entity may serve as an inductor group to control in turn the conformation of a neighboring dimethylpentane segment (cf. 7). This holds if the inducing dimethylpentane segment is isotactic (cf. 15, 25), but not when it is syndiotactic (cf. 28).
• Novel Cuticular Hydrocarbons from the Cane Beetle <i>Antitrogus parvulus</i>4,6,8,10,16-Penta- and 4,6,8,10,16,18-HexamethyldocosanesUnprecedented <i>anti-anti-anti</i>-Stereochemistry in the 4,6,8,10-Methyltetrad
  作者：Sharon Chow、Mary T. Fletcher、Lynette K. Lambert、Oliver P. Gallagher、Christopher J. Moore、Bronwen W. Cribb、Peter G. Allsopp、William Kitching

  DOI：10.1021/jo0481093

  日期：2005.3.1

  [GRAPHICS]The major cuticular hydrocarbons from the cane beetle species Antitrogus parvulus are 4,6,8,10,16-penta- and 4,6,8,10,16,18-hexamethyldocosanes, I and 2, respectively. Stereoisomers of 2,4,6,8-tetramethylundecanal of established relative stereochemistry were derived from 2,4,6-trimethylphenol and were then coupled with appropriate methyl-substituted phosphoranes 62 and 25 to furnish alkenes, which on reduction provided diastereomers of I and 2, respectively. Capillary gas chromatography, mass spectrometry, and high resolution C-13 NMR spectroscopy confirmed 1 as either 84a or 84b and 2 as either 15a or 15b. The novelty of these structures and their relative stereochemistry is briefly related to polyketide assembly.