(-)-phoracantholide-J | 69980-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: (-)-phoracantholide-J
• 英文别名: (R)-phoracantholide J；(R,Z)-10-methyl-3,4,7,8,9,10-hexahydro-2H-oxecin-2-one；(2R,6Z)-2-methyl-2,3,4,5,8,9-hexahydrooxecin-10-one
• CAS: 69980-00-3
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: UEQXZLBVNLFTBE-FIFYQCSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (-)-phoracantholide-J 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (R)-(-)-phoracantholide I
  参考文献：
  名称：

  挥发性两栖类信息素：来自马达加斯加的山tell类蛙的大环内酯类

  摘要：

  两栖动物喜欢水，但是他们也注意到空气中的挥发性化合物吗？是的，他们有。大环内酯类化合物，例如磷酰胺J（见图；右上图结构）或新发现的天然产物gephyromantolide A（左图结构），被马达加斯加的曼陀罗蛙用来交流。

  DOI：

  10.1002/anie.201106592
• 作为产物：
  描述：

  Thiocarbonic acid O-((Z)-(R)-2-methyl-10-oxo-3,4,5,8,9,10-hexahydro-2H-oxecin-4-yl) ester O-phenyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.5h， 以90%的产率得到(-)-phoracantholide-J
  参考文献：
  名称：

  New Silicon-Mediated, Sequential Ring Expansions of n-Sized 2-Cycloalkenones into Hydroxyolefinic n + m + p Medium-Sized Lactones:  Short Synthesis of (−)-Phoracantholide-J

  摘要：

  In only four steps from 2-cyclopentenone and 2-cyclohexenone, sequential three- or four-atom and then one- to three-atom ring enlargements produce nine- to 12-membered hydroxyolefinic lactones on a gram scale. 2-Cyclopentenone undergoes this serial 5 + 3 + 2 process to form 10-membered ring natural (-)-phoracantholide-J in six linear steps and 26% overall yield.

  DOI：

  10.1021/ol051854x

文献信息

• Lipase-mediated enantioselective acylation of alcohols with functionalized vinyl esters: acyl donor tolerance and applications
  作者：Robert Chênevert、Nicholas Pelchat、Pierre Morin

  DOI：10.1016/j.tetasy.2009.03.027

  日期：2009.6

  Enzymatic acylation is commonly used for the kinetic resolution of alcohols and amines. The simple acyl group introduced during the enzymatic reaction is Usually removed or replaced by another group. Retention of more complex acyl moieties as part of the target structures would be a more efficient strategy. We have studied the enantioselective acylation of a model alcohol substrate, 1-phenylethanol, with vinyl esters bearing various functionality on the acyl moieties in the presence of three lipases (Candida antarctica, Candida rugosa and Burkholderia cepacia) frequently used in organic synthesis. C. antarctica lipase is the most versatile lipase for this type of biotransformations. We applied this strategy to the synthesis of a protein kinase C ligand and a natural product, phoracantholide. (C) 2009 Elsevier Ltd. All rights reserved.
• Kitahara, Takeshi; Koseki, Koshi; Mori, Kenji, Agricultural and Biological Chemistry, 1983, vol. 47, # 2, p. 389 - 394
  作者：Kitahara, Takeshi、Koseki, Koshi、Mori, Kenji

  DOI：——

  日期：——
• Volatile Amphibian Pheromones: Macrolides from Mantellid Frogs from Madagascar
  作者：Dennis Poth、Katharina C. Wollenberg、Miguel Vences、Stefan Schulz

  DOI：10.1002/anie.201106592

  日期：2012.2.27

  Amphibians like water, but do they also notice volatile compounds in the air? Yes, they do. Macrolides, such as phoracantholide J (see picture; upper right structure) or the newly discovered natural product gephyromantolide A (left structure), are used for communication by mantelline frogs from Madagascar.

  两栖动物喜欢水，但是他们也注意到空气中的挥发性化合物吗？是的，他们有。大环内酯类化合物，例如磷酰胺J（见图；右上图结构）或新发现的天然产物gephyromantolide A（左图结构），被马达加斯加的曼陀罗蛙用来交流。
• New Silicon-Mediated, Sequential Ring Expansions of <i>n</i>-Sized 2-Cycloalkenones into Hydroxyolefinic <i>n</i> + <i>m</i> + <i>p</i> Medium-Sized Lactones:  Short Synthesis of (−)-Phoracantholide-J
  作者：Gary H. Posner、Mark A. Hatcher、William A. Maio

  DOI：10.1021/ol051854x

  日期：2005.9.1

  In only four steps from 2-cyclopentenone and 2-cyclohexenone, sequential three- or four-atom and then one- to three-atom ring enlargements produce nine- to 12-membered hydroxyolefinic lactones on a gram scale. 2-Cyclopentenone undergoes this serial 5 + 3 + 2 process to form 10-membered ring natural (-)-phoracantholide-J in six linear steps and 26% overall yield.