(E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-1-ol
• 英文别名: (E)-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-1-ol
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: AWQGUQFPTZSYBF-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,6,6-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate 、 (E)-4-(tributylstannyl)but-3-en-1-ol 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 三苯胂 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 5.0h， 以62%的产率得到(E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-1-ol
  参考文献：
  名称：

  Stereocontrolled Synthesis of 6-s-cis- and 6-s-trans-Locked 9Z-Retinoids by Hydroxyl-Accelerated Stille Coupling of (Z)-Tri-n-Butylstannylbut-2-en-1-ol and Bicyclic Dienyl Triflates

  摘要：

  Analogues of 9-cis-retinoic acid with locked 6-s-cis and 6-s-trans conformations have been stereoselectively synthesized using a Stille coupling reaction between bicyclic dienyl triflates (5 and 6, respectively) and (Z)-tributylstannylbut-2-en-1-ol (7) to stablish the Z geometry of the polyenic side chain. The mild conditions (25 degrees C, 30 min) of this coupling stand in contrast to the reluctance of the isomeric (E)-tributylstannylbut-2-en-1-ol (18) to react with triflates 5/6. The significant rate differences experimentally observed in Stille reactions between isomeric (Z)- and (E)-tri-n-butylstannylalkenols in favor of the former isomer, even with highly hindered alkenyl triflates, is ascribed to internal coordination of palladium to the heteroatom in the presumably rate-limiting transmetalation step. Dienals and trienals with an E geometry, which are not efficiently available by direct coupling of the corresponding triflates and E-stannanes, can in turn be obtained by isomerization of their Z-isomers.

  DOI：

  10.1021/jo9917588

文献信息

• Beneficial agent delivery systems
  申请人：Bruza J. Kenneth

  公开号：US20060018977A1

  公开（公告）日：2006-01-26

  An improved fragrance delivery system capable of providing controlled release of fragrance molecules in various consumer products is composed of a polymer having covalently bound fragrance moieties that are releasable in the form of fragrance molecules. Certain embodiments comprise globular polymer particles in which unbound fragrance molecules are occluded, absorbed and/or adsorbed. Certain other embodiments incorporate fragrance monomer units, which achieve reduced residuals upon complete release of the fragrance.

  一种改进的香气释放系统，能够在各种消费品中提供香气分子的受控释放，由具有共价结合的香气基团的聚合物组成，这些基团可以以香气分子的形式释放。某些实施例包括球形聚合物颗粒，其中未结合的香气分子被包含、吸收和/或吸附。某些其他实施例包括香气单体单元，这些单元在完全释放香气后实现减少残留物。
• Compounds for a controlled release of active compounds
  申请人：——

  公开号：US20040048754A1

  公开（公告）日：2004-03-11

  The present invention relates to the field of perfumery. More particularly, it concerns a compound having supported carbamoyl/ester moieties which comprise an ester capable of liberating an active compound and, in proximity, a carbamoyl function facilitating the release of the active compound. The present application concerns also the uses of such compounds as active ingredient or as a precursor capable of liberating active alcohols, ketones or aldehydes, as well as compositions comprising such compounds.

  本发明涉及香料领域。更具体地，它涉及一种具有支持的氨基甲酰/酯基官能团的化合物，其中包括能够释放活性化合物的酯基，以及在其附近的氨基甲酰功能，有助于释放活性化合物。本申请还涉及这种化合物作为活性成分或作为能够释放活性醇，酮或醛的前体的用途，以及包含这种化合物的组合物。
• COMPOUNDS FOR A CONTROLLED RELEASE OF ACTIVE COMPOUNDS
  申请人：FIRMENICH SA

  公开号：EP1373368A1

  公开（公告）日：2004-01-02
• US7723285B2
  申请人：——

  公开号：US7723285B2

  公开（公告）日：2010-05-25
• [EN] COMPOUNDS FOR A CONTROLLED RELEASE OF ACTIVE COMPOUNDS<br/>[FR] COMPOSES SERVANT A EFFECTUER LA LIBERATION CONTROLEE DE COMPOSES ACTIFS
  申请人：FIRMENICH & CIE

  公开号：WO2002077074A1

  公开（公告）日：2002-10-03

  The present invention relates to the field of perfumery. More particularly, it concerns a compound having supported carbamoyl/ester moieties which comprise an ester capable of liberating an active compound and, in proximity, a carbamoyl function facilitating the release of the said active compound. The present application concerns also the uses of said compound, as well as the compositions comprising said compounds.