((S)-1-((R)-pent-4-en-2-yloxy)allyloxy)cyclohexane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((S)-1-((R)-pent-4-en-2-yloxy)allyloxy)cyclohexane
• 英文别名: [(1S)-1-[(2R)-pent-4-en-2-yl]oxyprop-2-enoxy]cyclohexane
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: WQTKEFGSNALWNV-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((S)-1-((R)-pent-4-en-2-yloxy)allyloxy)cyclohexane 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(2R,6S)-6-(cyclohexyloxy)-2-methyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Pd-Catalyzed Asymmetric Intermolecular Hydroalkoxylation of Allene: An Entry to Cyclic Acetals with Activating Group-Free and Flexible Anomeric Control

  摘要：

  A ligand-directed metal-catalyzed asymmetric intermolecular hydroalkoxylation of alkoxyallene is reported. Combined with ring-closing-metathesis, this reaction offers a new atom-efficient synthetic method toward various cyclic acetals with elaborate anomeric control. Synthetic utility of the reaction was demonstrated by the atom-efficient and stereodivergent access to various mono- and disaccharides.

  DOI：

  10.1021/ja508587f
• 作为产物：
  描述：

  (R)-(-)-4-烯基-2-戊醇 、 cyclohexyloxyallene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 (1R,2R)-(+)-1,2-二氨基环己烷-N,N′-双(2-二苯基磷苯甲酰) 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以94%的产率得到((S)-1-((R)-pent-4-en-2-yloxy)allyloxy)cyclohexane
  参考文献：
  名称：

  Pd-Catalyzed Asymmetric Intermolecular Hydroalkoxylation of Allene: An Entry to Cyclic Acetals with Activating Group-Free and Flexible Anomeric Control

  摘要：

  A ligand-directed metal-catalyzed asymmetric intermolecular hydroalkoxylation of alkoxyallene is reported. Combined with ring-closing-metathesis, this reaction offers a new atom-efficient synthetic method toward various cyclic acetals with elaborate anomeric control. Synthetic utility of the reaction was demonstrated by the atom-efficient and stereodivergent access to various mono- and disaccharides.

  DOI：

  10.1021/ja508587f

文献信息

• Pd-Catalyzed Asymmetric Intermolecular Hydroalkoxylation of Allene: An Entry to Cyclic Acetals with Activating Group-Free and Flexible Anomeric Control
  作者：Wontaeck Lim、Jungjoon Kim、Young Ho Rhee

  DOI：10.1021/ja508587f

  日期：2014.10.1

  A ligand-directed metal-catalyzed asymmetric intermolecular hydroalkoxylation of alkoxyallene is reported. Combined with ring-closing-metathesis, this reaction offers a new atom-efficient synthetic method toward various cyclic acetals with elaborate anomeric control. Synthetic utility of the reaction was demonstrated by the atom-efficient and stereodivergent access to various mono- and disaccharides.