trans-(+/-)-4-cyclohexyl-3-methyloxetan-2-one | 114049-50-2

• 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: trans-(+/-)-4-cyclohexyl-3-methyloxetan-2-one
• 英文别名: (3S,4S)-4-cyclohexyl-3-methyloxetan-2-one
• CAS: 114049-50-2
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: XESPNBJGWJLHIN-IONNQARKSA-N

物化性质

• 沸点：
  259.4±9.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  trans-(+/-)-4-cyclohexyl-3-methyloxetan-2-one 在 magnesium bromide 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以75%的产率得到3-methyl-1-oxaspiro<4.5>decan-2-one
  参考文献：
  名称：

  Dyotropic rearrangement of cycloalkyl .beta.-lactones. Formation of spiro versus fused butyrolactones as a function of ring size

  摘要：

  DOI：

  10.1021/jo00260a021
• 作为产物：
  描述：

  环己烷基甲醛 在 苯磺酰氯 、 lithium diisopropyl amide 作用下， 以 吡啶 为溶剂， 反应 33.0h， 生成 trans-(+/-)-4-cyclohexyl-3-methyloxetan-2-one
  参考文献：
  名称：

  Dyotropic rearrangement of cycloalkyl .beta.-lactones. Formation of spiro versus fused butyrolactones as a function of ring size

  摘要：

  DOI：

  10.1021/jo00260a021

文献信息

• Catalyzed acyl halidealdehyde cyclocondensations. New insights into the design of catalytic cross aldol reactions
  作者：Scott G. Nelson、Zhonghui Wan、Timothy J. Peelen、Keith L. Spencer

  DOI：10.1016/s0040-4039(99)01308-8

  日期：1999.9

  quantities (2.5–20 mol%) of Al(SbF6)3 catalyze the di(isopropyl)ethylamine-mediated cyclocondensation of various acyl halides and enolizable aldehydes to afford β-lactones in good yields (58–93%). These reactions are discussed as a strategy for executing chemo- and regiospecific catalyzed cross aldol reactions.

  Al（SbF 6）3的亚化学计量量（2.5–20 mol％）催化二（异丙基）乙胺介导的各种酰基卤和可烯醇化醛的环缩合反应，从而以高收率（58–93％）提供β-内酯。这些反应被讨论为执行化学和区域特异性催化的交叉羟醛缩合反应的策略。
• Catalytic Asymmetric Synthesis of trans-Configured β-Lactones: Cooperation of Lewis Acid and Ion Pair Catalysis
  作者：Thomas Kull、José Cabrera、René Peters

  DOI：10.1002/chem.201000840

  日期：——

  development of the first trans‐selective catalytic asymmetric [2+2] cyclocondensation of acyl halides with aliphatic aldehydes furnishing 3,4‐disubstituted β‐lactones is described. This work made use of a new strategy within the context of asymmetric dual activation catalysis: it combines the concepts of Lewis acid and organic aprotic ion pair catalysis in a single catalyst system. The methodology could

  描述了酰基卤与脂肪族醛（提供3,4-二取代的β-内酯）的首次反式选择性催化不对称[2 + 2]环缩合反应的发展。这项工作在不对称双活化催化的背景下利用了一种新的策略：它将路易斯酸和有机质子惰性离子对催化的概念结合在一个单一的催化剂体系中。该方法还可以应用于芳族醛，并具有广泛的适用性（29个示例）。亲核开环反应进一步证明了其实用性，该反应提供了高度对映体富集的抗醛醇缩合产物。
• Studies of the tandem Mukaiyama aldol-lactonization (TMAL) reaction: A concise and highly diastereoselective route to β-lactones applied to the total synthesis of the potent pancreatic lipase inhibitor, (−)-Panclicin D
  作者：Hong Woon Yang、Cunxiang Zhao、Daniel Romo

  DOI：10.1016/s0040-4020(97)01029-6

  日期：1997.12

  A concise and highly diastereoselective route to β-lactones has been developed based on a tandem Mukaiyama aldol-lactonization employing thiopyridylsilylketene acetals and various aldehydes. (−)-Panclicin D, a potent pancreatic lipase inhibitor, was synthesized using this methodology. Recent optimization and extensions of this method are described which include variation of the silyl group and leaving

  基于使用硫代吡啶基甲硅烷基乙烯酮缩醛和各种醛类的串联Mukaiyama醇醛内酯化法，已开发出一种简洁且高度非对映选择性的β-内酯途径。使用这种方法合成了一种有效的胰脂肪酶抑制剂（-）-PanclicinD。描述了该方法的最近的优化和扩展，其包括乙烯酮缩醛的甲硅烷基和离去基团的变化。
• A Highly Diastereoselective, Tandem Mukaiyama Aldol-Lactonization Route to β-Lactones:  Application to a Concise Synthesis of the Potent Pancreatic Lipase Inhibitor, (−)-Panclicin D
  作者：Hong Woon Yang、Daniel Romo

  DOI：10.1021/jo9619488

  日期：1997.1.1
• A Stereocomplementary Approach to β-Lactones:  Highly Diastereoselective Synthesis of <i>cis</i>-β-Lactones, a β-Chloro Acid, and a Tetrahydrofuran
  作者：Yingcai Wang、Cunxiang Zhao、Daniel Romo

  DOI：10.1021/ol990860o

  日期：1999.10.1

  [GRAPHICS]In the course of mechanistic studies of the ZnCl2-mediated tandem Mukaiyama aldol-lactonization reaction of aldehydes and thiopyridyl ketene acetals, a stereocomplementary reaction employing SnCl4 was discovered. This method provides a highly diastereoselective entry to cis-1,2-disubstituted beta-lactones as well as a beta-chloro carboxylic acid and a tetrahydrofuran. The former products were obtained by varying the reaction temperature. The latter product was obtained when the aldehyde substrate bore a pendant silyl ether.