(+/-)-3-methyl-3-(4-methyl-3-pentenyl)cyclohexanone | 172921-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-3-methyl-3-(4-methyl-3-pentenyl)cyclohexanone
• 英文别名: 3-methyl-3-(4-methylpent-3-enyl)cyclohexanone；3-Methyl-3-(4-methyl-3-penten-1-yl)cyclohexanone；3-methyl-3-(4-methylpent-3-enyl)cyclohexan-1-one
• CAS: 172921-88-9
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: XQBKPFBGVPNIJM-UHFFFAOYSA-N

物化性质

• 沸点：
  269.5±9.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  (+/-)-3-methyl-3-(4-methyl-3-pentenyl)cyclohexanone 在 4-二甲氨基吡啶 、 sodium dodecyl-sulfate 、 N-甲基吗啉氧化物 、 2-碘酰基苯甲酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 19.5h， 生成 2-hydroxymethyl-5-methyl-5-(4-methylpent-3-enyl)-2-cyclohexenone
  参考文献：
  名称：

  实现 Vibsanin E、15-O-甲基环病毒素 B、3-Hydroxyvibsanin E、呋喃病毒素 A 和 3-O-甲基呋喃病毒素 A 的全合成

  摘要：

  详细介绍了各种生物合成相关 vibsanin 型二萜（即 vibsanin E、15-O-甲基环蛋白 B、3-羟基-vibsanin E、呋喃-vibsanin A 和 3-O-methylfuranovibsanin A）的合成方法的研究。生物遗传学建模方法与经典和现代六到七元环扩展协议的研究相结合，可以获得对这些天然产物的中心核心的访问。(c) Wiley-VCH Verlag GmbH & Co.

  DOI：

  10.1002/ejoc.200600246
• 作为产物：
  描述：

  (E)-6,10-dimethylundeca-1,5,9-triene 生成 (+/-)-3-methyl-3-(4-methyl-3-pentenyl)cyclohexanone
  参考文献：
  名称：

  潜在的安布拉香精的合成：5,5,9-三甲基癸基衍生物。

  摘要：

  AbstractThe synthesis of racemic stereoisomeric compounds with the 5,5,9‐trimethyldecalin skeleton and an oxygen function at C(1), C(2), or C(3) is describedAlthough racemic decalins are described, only the enantiomer related to steroids is drawn. The projection of the decalins was chosen so as to place the angular methyl group above the plane of the molecule and the oxygen function at C(1), C(2) or C(3) on the left side, as represented by formula 1–6. The relative configuration of the substituents in decalins is designated by using the convention of the steroid series: β, meaning on the same side as the angular methyl group at C(9) and α, meaning on the side opposite from the angular methyl group. The prefix cis or trans refers to the fusion of the decalin ring system, not to the position of the substituents. . A novel general one‐step synthesis of 2‐decalones by means of acid catalyzed cyclization of acyclic or monocyclic precursors has been developed.

  DOI：

  10.1002/hlca.19730560425

文献信息

• Towards the Total Synthesis of Spirovibsanin A: Total Synthesis of (±)-5,14-Bis-<i>epi</i>-spirovibsanin A
  作者：Michael J. Gallen、Craig M. Williams

  DOI：10.1002/ejoc.200800574

  日期：2008.9

  Studies towards the total synthesis of the complex diterpene spirovibsanin A are herein presented, which culminate in an 18-step total synthesis. Considering the perceived stereochemical uncertainty surrounding the assignment of spirovibsanin A these studies have allowed a direct spectroscopic comparison of the (±)-5,14-bis-epi derivative to that of natural spirovibsanin A demonstrating that the carbon

  本文介绍了对复合二萜 spirovibsanin A 全合成的研究，该研究在 18 步全合成中达到高潮。考虑到围绕 spirovibsanin A 分配的立体化学不确定性，这些研究允许将 (±)-5,14-bis-epi 衍生物与天然 spirovibsanin A 的衍生物进行直接光谱比较，证明碳骨架和立体化学分配给天然 spirovibsanin A 很可能是正确的。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）
• Construction of the Cyclovibsanin Core via a Biogenetically Modeled Approach
  作者：David P. Tilly、Craig M. Williams、Paul V. Bernhardt

  DOI：10.1021/ol051897d

  日期：2005.11.1

  [reaction: see text] Construction of the 15-O-methylcyclovibsanin B core was achieved expediently in eight linear steps utilizing a biogenetically modeled approach.

  [反应：见正文]利用生物遗传学建模方法，可通过八个线性步骤方便地完成15-O-甲基环维沙星B核的构建。
• Synthesis of Carbocycles via Intramolecular Conjugate Additions:  Total Syntheses of Axane Sesquiterpenoids
  作者：Alyx-Caroline Guevel、David J. Hart

  DOI：10.1021/jo951532e

  日期：1996.1.1

  Syntheses of (+/-)-axamide-1 (2) and (+/-)-axisonitrile-1 (1) are described. The syntheses require 12 steps and 13 steps, respectively, from vinylogous ester 8 and feature the diastereoselective cyclization of unsaturated ester 7 to perhydroindan 5. Some interesting reactions of the organometallic derived from [(trimethylsilyl)methyl]magnesium chloride and cerium trichloride are also described.

  描述了（+/-）-ax酰胺-1（2）和（+/-）-轴腈-1（1）的合成。合成需要分别从乙烯基酯8到12步和13步，并且具有不饱和酯7到非氢茚满5的非对映选择性环化的特点。还描述了一些有趣的有机金属化合物的反应，这些有机金属化合物来自[[（三甲基甲硅烷基）甲基]氯化镁和三氯化铈。 。
• Synthetic neovibsanes and their ability to induce neuronal differentiation in PC12 cells
  作者：P.-J. Chen Annette、C. Catharina Müller、Helen M. Cooper、Craig M. Williams

  DOI：10.1016/j.tet.2010.06.056

  日期：2010.8

  A series of neovibsanin A and B derivatives and lower homologues were synthesized to study their neurotrophic ability with PC12 cells. 4,5-Bis-epi-neovibsanin A displayed prominent ability to induce neurite outgrowth compared to control cultures. Herein we describe the total synthesis of 4,5-bis-epi-neovibsanin A and B as well as comparing the biological activity of several neovibsane derivatives. (C) 2010 Elsevier Ltd. All rights reserved,
• Expedient Construction of the Vibsanin E Core without the Use of Protecting Groups
  作者：Ralf Heim、Stefan Wiedemann、Craig M. Williams、Paul V. Bernhardt

  DOI：10.1021/ol0501222

  日期：2005.3.1

  The tricyclic core of vibsanin E was constructed without the use of a protecting group in six steps. The El Gaied Baylis-Hillman variant was key to allowing the Bronsted acid induced tandem cyclization forming rings B and C in one operation.