(E)-2-(3-methylhepta-2,6-dien-1-yl)phenol | 752209-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-(3-methylhepta-2,6-dien-1-yl)phenol
• 英文别名: 2-(3-methylhepta-2,6-dienyl)phenol；2-[(2E)-3-methylhepta-2,6-dienyl]phenol
• CAS: 752209-08-8
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: SWVFVWJTAGJEFT-ZRDIBKRKSA-N

物化性质

• 沸点：
  328.1±21.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-(3-methylhepta-2,6-dien-1-yl)phenol 在 silver tetrafluoroborate 、 三甲基乙腈 、 xenon fluoride 、 六甲基二硅氧烷 、 C₄₈H₅₀I₂P₂Pt 作用下， 反应 3.0h， 以56%的产率得到(2R,4aR)-2-fluoro-4a-methyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene
  参考文献：
  名称：

  Catalytic Enantioselective Cyclization and C3-Fluorination of Polyenes

  摘要：

  (Xylyl-phanephos)Pt2+ in combination with XeF2 mediates the consecutive diastereoselective cation-olefin cyclization/fluorination of polyene substrates. Isolated yields were typically in the 60-69% range while enantioselectivities reached as high as 87%. The data are consistent with a stereoretentive fluorination of a P2Pt-alkyl cation intermediate.

  DOI：

  10.1021/ja3116795
• 作为产物：
  描述：

  香叶醇 在 盐酸 、 sodium periodate 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 magnesium 、 2,2-二甲基-1,3-丙二醇 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 65.0h， 生成 (E)-2-(3-methylhepta-2,6-dien-1-yl)phenol
  参考文献：
  名称：

  Pd（II）和Pt（II）介导的1,5-和1,6-二烯的多环化反应：支持碳正离子中间体的证据。

  摘要：

  DOI：

  10.1002/anie.200453913

文献信息

• Pd(II)-Catalyzed cyclogeneration of carbocations: subsequent rearrangement and trapping under oxidative conditions
  作者：Jeong Hwan Koh、Cheryl Mascarenhas、Michel R. Gagné

  DOI：10.1016/j.tet.2004.06.023

  日期：2004.8

  A catalytic oxidative polycyclization reaction initiated by the carbocyclization of 1,5-dienes with Pd(II) is reported. Trapping of a putative carbocation with suitable functional groups (phenols, alkenes, alcohols, sulfonamide), or rearrangement protocols (Pinacol) yields poly-cyclic products in good yields and in excellent diastereoselectivities. Turnover of the intermediate Pd–C bond is via β-H

  据报道，由1,5-二烯与Pd（II）的碳环化引发的催化氧化多环化反应。用合适的官能团（苯酚，烯烃，醇，磺酰胺）或重排方案（Pinacol）捕获假定的碳阳离子可得到高收率和出色的非对映选择性的多环产物。中间Pd–C键的周转是通过β-H消除。
• Regioselective Oxidative Cation-Olefin Cyclization of Poly-enes:  Catalyst Turnover via Hydride Abstraction
  作者：Charles A. Mullen、Michel R. Gagné

  DOI：10.1021/ja073573l

  日期：2007.10.1

  Electrophilic P2Pt2+ complexes are shown to catalyze the regio- and diastereoselective oxidative cascade cyclization of poly-enes. The reactions are stereospecific with respect to the initiating alkenes geometry and suggest an all-chair, semiconcerted transition structure. Catalyst turnover after cyclization apparently occurs via beta-hydride elimination and subsequent hydride abstraction (from P2Pt-H+) by added Trityl cation (in the form of trityl methyl ether or a resin version thereof) to regenerate the active P(2)pt(2+) state. One intriguing possibility is that the high regioselectivity observed in the beta-H elimination is due to a regio-defining beta-agostic resting state.
• PdII- and PtII-Mediated Polycyclization Reactions of 1,5- and 1,6-Dienes: Evidence in Support of Carbocation Intermediates
  作者：Jeong Hwan Koh、Michel R. Gagné

  DOI：10.1002/anie.200453913

  日期：2004.6.28
• Catalytic Enantioselective Cyclization and C3-Fluorination of Polyenes
  作者：Nikki A. Cochrane、Ha Nguyen、Michel R. Gagne

  DOI：10.1021/ja3116795

  日期：2013.1.16

  (Xylyl-phanephos)Pt2+ in combination with XeF2 mediates the consecutive diastereoselective cation-olefin cyclization/fluorination of polyene substrates. Isolated yields were typically in the 60-69% range while enantioselectivities reached as high as 87%. The data are consistent with a stereoretentive fluorination of a P2Pt-alkyl cation intermediate.