1-乙酰基-2-(2-丙烯基)环己烷 | 36306-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-乙酰基-2-(2-丙烯基)环己烷
• 英文名称: 1-Acetyl-2-allylcyclohexane
• 英文别名: 1-(2-prop-2-enylcyclohexyl)ethanone
• CAS: 36306-62-4
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: XUWDLBUKPBKIIH-UHFFFAOYSA-N

物化性质

• 沸点：
  231.9±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
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  1-乙酰基-2-(2-丙烯基)环己烷 在 sodium 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 1-乙酰基-2-(2-丙烯基)环己烷
  参考文献：
  名称：

  含不饱和取代环烷基的α-重氮β-酮腈的铑催化分子内环丙烷化

  摘要：

  制备了几种带有反式-2-烯丙基-、-乙烯基-或-苯基环烷基的α-重氮β-酮腈，并研究了它们的分子内环丙烷化反应。在 Rh2(OAc)4 (1 mol%) 作为催化剂存在下，发现烯丙基和乙烯基取代的前体在环境温度下顺利进行环丙烷化，以 47-88% 的产率提供新型三环 α-酮基环丙基腈非对映体比例范围为 79:21 至 >99:1。另一方面，含苯基类似物的催化反应没有产生任何环丙基产物，而是以定量产率提供官能化的六氢菲或四氢环戊萘衍生物。

  DOI：

  10.1055/s-0036-1588174
• 作为产物：
  描述：

  1-Allyl-2-(1-nitro-ethyl)-cyclohexane 在 cethyltrimethylammonium permanganate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以67%的产率得到1-乙酰基-2-(2-丙烯基)环己烷
  参考文献：
  名称：

  Vankar, Padma S.; Rathore, R.; Chandrasekaran, S., Synthetic Communications, 1987, vol. 17, # 2, p. 195 - 202

  摘要：

  DOI：

文献信息

• [3+2] cycloadditions of allylsilanes - 4.
  作者：Hans-Joachim Knölker、Norbert Foitzik、Regina Graf、Jörn-Bernd Pannek、Peter G Jones

  DOI：10.1016/s0040-4020(01)80193-9

  日期：1993.1

  reaction of allyltrimethylsilane with enones is shown to afford the 3-allyl ketone derivatives (Sakurai products) along with the trimethylsilylcyclopentanes ([3+2] cycloaddition products). The stereochemistry of the [3+2] cycloaddition products is determined by X-ray analysis.

  烯丙基三甲基硅烷与烯酮的路易斯酸促进的反应显示，与三甲基甲硅烷基环戊烷（[3 + 2]环加成产物）一起提供了3-烯丙基酮衍生物（樱井产品）。通过X射线分析确定[3 + 2]环加成产物的立体化学。
• Route to Highly Substituted Pyridines
  作者：Justin A. Hilf、Michael S. Holzwarth、Scott D. Rychnovsky

  DOI：10.1021/acs.joc.6b01370

  日期：2016.11.4

  Pyridine rings are common structural motifs found in a number of biologically active compounds, including some top-selling pharmaceuticals. We have developed a new approach to access substituted pyridines. The method aims to provide a reliable synthesis of a diverse range of substituted pyridines through a three-step procedure. Readily available enones are first converted into 1,5-dicarbonyls through

  吡啶环是在许多生物活性化合物（包括一些畅销药物）中发现的常见结构基序。我们已经开发出一种新的方法来获得取代的吡啶。该方法旨在通过三步法提供可靠的合成范围广泛的取代吡啶。易于获得的烯酮首先通过两步Hosomi-Sakurai烯丙基化/氧化裂解序列转化为1,5-二羰基，然后使用盐酸羟胺将其环化为相应的吡啶。使用该方法已经合成了多种取代的吡啶。
• Cycloadditions of allylsilanes, part 14. Enantiospecific synthesis of bicyclo[4.3.0]nonanes by asymmetric [3+2] cycloaddition of chiral allylsilanes
  作者：Hans-Joachim Knölker、Norbert Foitzik、Oliver Schmitt

  DOI：10.1016/s0040-4039(99)00551-1

  日期：1999.4

  The titanium tetrachloride promoted [3+2] cycloaddition of (R)-(1-phenylprop-2-enyl)trimethylsilane (R)-4 (82% ee) and 1-acetylcyclo-hexene 1 provides an enantiospecific route to the bicyclo[4.3.0]nonane (+)-6.

  （R）-（1-苯基丙-2-烯基）三甲基硅烷（R）-4（82％ee）和1-乙酰基环己烯1的四氯化钛促进的[3 + 2]环加成反应提供了双环[ 4.3.0]壬烷（+）- 6。
• Highly Stereoselective Synthesis of Bicyclo[n.3.0]alkanes by Titanium Tetrachloride Promoted [3 + 2] Cycloaddition of Allylsilanes and 1-Acetylcycloalkenes
  作者：Hans-Joachim Knölker、Norbert Foitzik、Helmut Goesmann、Regina Graf、Peter G. Jones、Günter Wanzl

  DOI：10.1002/chem.19970030409

  日期：1997.4

  AbstractThe titanium tetrachloride promoted reaction of allylsilanes 1 with 1‐acetylcyclohexene is shown to afford the silylbicyclo[4.3.0]nonanes 9 ([3 + 2] cycloaddition products) along with the 1‐acetyl‐2‐allylcyclohexane 4 (Hosomi‐Sakurai product). Here we report that systematic variation of the substituents at the silicon atom of 1 allows suppression of the classical Hosomi‐Sakurai reaction in favor of the [3 + 2] cycloaddition. Cycloaddition of the allylsilanes 1 d, 1 i, and 1 k with 1‐acetylcycloalkenes 10, containing a 5‐, 6‐, 7‐, 8‐, or 12‐membered ring, gives rise to the corresponding silylbicyclo[n.3.0]alkanes 11 – 13. The cycloaddition of allyltriisopropylsilane (1 k) and 1‐acetyl‐2‐methylcycloalkenes 15 provides silylbicyclo[n.3.0]alkanes 16 with two contiguous quaternary carbon centers. The stereochemistry of the silylbicyclo[n.3.0]alkanes 11 a ‐ c and 14 is unambiguously determined by X‐ray analysis and 13C NMR spectroscopy.
• Access to Functionalized Bicyclo[4,3,0]nonenes via Palladium-Catalyzed Oxidative Cyclization of 2-Allylcyclohexyl Oximes
  作者：Jia-Liang Zhu、Sih-Ting Wu、Jr-Yun Shie

  DOI：10.1021/jo5005422

  日期：2014.4.18

  A new palladium-catalyzed oxidative cyclization process leading to the functionalized bicyclo[4,3,0]nonenes is serendipitously discovered during attempts to form azaheterocycle by the amino-Heck reaction of trans-2-vinyl-clohexyl phosphinyloxime. Under the influence of Pd(dba)(2)/Et3N/1:1 N-2-O-2 (1:1, v/v) (Method A) or Pd(OAc)(2)/Et3N/O-2 (Method B), the reactions afford the substituted cis-1-hydroxyl-8-formyl-bicyclo[4,3,0]non-8(9)-enes or bicycle[4,3,0]non-1(9)-en-8-ones in varying yields with the incorporation of molecular oxygen into the structures. The 5,6-bicyclic scaffold of these products is presumably derived from tandem double intramolecular cyclization followed by the ring-opening of an aza-palladium(II) tricyclic intermediate.