尼艾酚 | 96895-25-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: 尼艾酚
• 中文别名: 2-丁酮,1-(3-甲基-2(3H)-苯并噻唑亚基)-
• 英文名称: (-)-Nyasol
• 英文别名: (3R)-cis-hinokiresinol；nyasol；(Z)-1,3-bis(4-hydroxyphenyl)-1,4-pentadiene；(-)-cis-nyasol；4-[(1Z,3R)-3-(4-hydroxyphenyl)penta-1,4-dienyl]phenol
• CAS: 96895-25-9
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: VEAUNWQYYMXIRB-JHAQOBCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-硼双环[3.3.1]壬烷 、 尼艾酚 以 四氢呋喃 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  立体异构纯三取代乙烯基铝试剂及其在铜催化对映选择性合成含 Z 或 E 烯烃的 1,4-二烯中的应用

  摘要：

  通过甲硅烷基取代的炔烃的区域选择性和立体选择性氢铝化以及随后的对映选择性铜催化烯丙基烷基化，可以很容易地获得含有E或Z双键的手性 1,4-二烯的所需异构体。通过 (-)-nyasol 的合成证明了该程序的实用性（参见方案）。dibal-H=二异丁基氢化铝，NHC=N-杂环卡宾。

  DOI：

  10.1002/anie.200905223
• 作为产物：
  描述：

  (R,Z)-4,4'-(penta-1,4-diene-1,3-diyl)bis(methoxybenzene) 在 甲基碘化镁 作用下， 以 乙醚 为溶剂， 160.0 ℃ 、20.0 kPa 条件下， 反应 1.0h， 以80%的产率得到尼艾酚
  参考文献：
  名称：

  Iridium-Catalyzed Enantioselective Allylic Vinylation

  摘要：

  The first example of Ir-catalyzed asymmetric substitution reaction with vinyl trifluoroborates is described. The direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates proceeded with high site selectivity and excellent enantioselectivity (up to 99%) mediated by an Ir-(P,olefin) complex. This method allows rapid access to various 1,4-dienes or trienes including the biologically active natural products (-)-nyasol and (-)-hinokiresinol.

  DOI：

  10.1021/ja311422z

文献信息

• Composition Comprising the Extract of Anemarrhena Asphodeloides Bunge or the Compounds Isolated from the Same for Preventing and Treating Lipid Metabolism Disorder
  申请人：Seo Eun Kyoung

  公开号：US20120070515A1

  公开（公告）日：2012-03-22

  The present invention relates to a composition comprising an extract of Anemarrhena asphodeloides Bunge or the compounds isolated from the same, as an active ingredient. In particular, the extract and compounds have the excellent inhibitory effects on adipocyte differentiation, and thus can be used in a pharmaceutical composition and functional food for the prevention and treatment of lipid metabolism disorders.

  本发明涉及一种包含知母提取物或从中分离出的化合物的组合物，作为活性成分。具体来说，该提取物和化合物具有出色的抑制脂肪细胞分化作用，因此可用于制备用于预防和治疗脂质代谢紊乱的药物组合物和功能性食品。
• US8431166B2
  申请人：——

  公开号：US8431166B2

  公开（公告）日：2013-04-30
• [EN] COMPOSITION COMPRISING THE EXTRACT OF ANEMARRHENA ASPHODELOIDES BUNGE OR THE COMPOUNDS ISOLATED FROM THE SAME FOR PREVENTING AND TREATING LIPID METABOLISM DISORDER<br/>[FR] COMPOSITION COMPRENANT UN EXTRAIT D'ANEMARRHENA ASPHODELOIDES BUNGE OU LES COMPOSÉS ISOLÉS À PARTIR DE CELLE-CI POUR PRÉVENIR ET TRAITER LES TROUBLES DU MÉTABOLISME LIPIDIQUE
  申请人：UNIV EWHA IND COLLABORATION

  公开号：WO2010120029A1

  公开（公告）日：2010-10-21

  The present invention relates to a composition comprising an extract of Anemarrhena asphodeloides Bunge or the compounds isolated from the same, as an active ingredient. In particular, the extract and compounds have the excellent inhibitory effects on adipocyte differentiation, and thus can be used in a pharmaceutical composition and functional food for the prevention and treatment of lipid metabolism disorders.
• Stereoisomerically Pure Trisubstituted Vinylaluminum Reagents and their Utility in Copper‐Catalyzed Enantioselective Synthesis of 1,4‐Dienes Containing <i>Z</i> or <i>E</i> Alkenes
  作者：Katsuhiro Akiyama、Fang Gao、Amir H. Hoveyda

  DOI：10.1002/anie.200905223

  日期：2010.1.8

  The desired isomer of a chiral 1,4‐diene containing an E or Z double bond can be accessed readily by a regio‐ and stereoselective hydroalumination of silyl‐substituted alkynes and subsequent enantioselective copper‐catalyzed allylic alkylation. The utility of the procedure was demonstrated through the synthesis of (−)‐nyasol (see scheme). dibal‐H=diisobutylaluminum hydride, NHC=N‐heterocyclic carbene

  通过甲硅烷基取代的炔烃的区域选择性和立体选择性氢铝化以及随后的对映选择性铜催化烯丙基烷基化，可以很容易地获得含有E或Z双键的手性 1,4-二烯的所需异构体。通过 (-)-nyasol 的合成证明了该程序的实用性（参见方案）。dibal-H=二异丁基氢化铝，NHC=N-杂环卡宾。
• Iridium-Catalyzed Enantioselective Allylic Vinylation
  作者：James Y. Hamilton、David Sarlah、Erick M. Carreira

  DOI：10.1021/ja311422z

  日期：2013.1.23

  The first example of Ir-catalyzed asymmetric substitution reaction with vinyl trifluoroborates is described. The direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates proceeded with high site selectivity and excellent enantioselectivity (up to 99%) mediated by an Ir-(P,olefin) complex. This method allows rapid access to various 1,4-dienes or trienes including the biologically active natural products (-)-nyasol and (-)-hinokiresinol.