(E)-4-methyl-7-phenylhept-4-en-1-ol | 162085-15-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-4-methyl-7-phenylhept-4-en-1-ol
• CAS: 162085-15-6
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: FZCDEWMVNASJSU-NTUHNPAUSA-N

物化性质

• 沸点：
  330.8±21.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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)-4-methyl-7-phenylhept-4-en-1-ol 在 18-冠醚-6 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-5-methyl-8-phenyloct-5-enenitrile
  参考文献：
  名称：

  Catalytic Diastereoselective Polycyclization of Homo(polyprenyl)arene Analogues Bearing Terminal Siloxyvinyl Groups

  摘要：

  Highly diastereoselective polycyclization of homo(polyprenyl) arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4 alpha(equatorial)- and 4 beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4 alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4 beta-preference.

  DOI：

  10.1021/ol062378t
• 作为产物：
  描述：

  (E)-6-acetoxy-4-methyl-4-hexenal 在 咪唑 、 sodium tetrahydroborate 、 四丁基氟化铵 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 (E)-4-methyl-7-phenylhept-4-en-1-ol
  参考文献：
  名称：

  Catalytic Diastereoselective Polycyclization of Homo(polyprenyl)arene Analogues Bearing Terminal Siloxyvinyl Groups

  摘要：

  Highly diastereoselective polycyclization of homo(polyprenyl) arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4 alpha(equatorial)- and 4 beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4 alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4 beta-preference.

  DOI：

  10.1021/ol062378t

文献信息

• Acid-Catalyzed Intramolecular [2+2] Cycloaddition of Ene-allenones: Facile Access to Bicyclo[<i>n</i>.2.0] Frameworks
  作者：Jun-Feng Zhao、Teck-Peng Loh

  DOI：10.1002/anie.200902471

  日期：2009.9.14

  Two plus two equals a bicycle: A highly efficient acid‐catalyzed intramolecular [2+2] cycloaddition of ene‐allenones affords strained bicyclo[n.2.0] frameworks, which contain vicinal all‐carbon quaternary and tertiary centers (see scheme; Tf: trifluoromethanesulfonyl), under mild conditions with excellent yields and chemo‐, regio‐, and diastereoselectivities.

  2加2等于一辆自行车：烯丙烯酮的高效酸催化的分子内[2 + 2]环加成反应产生了紧张的双环[ n]。[2.0]框架，其中包含临近的全碳四级和三级中心（请参阅方案； Tf：三氟甲磺酰基），在温和的条件下具有出色的产率和化学，区域和非对映选择性。
• Organoselenium-Catalyzed Synthesis of Oxygen- and Nitrogen-Containing Heterocycles
  作者：Ruizhi Guo、Jiachen Huang、Haiyan Huang、Xiaodan Zhao

  DOI：10.1021/acs.orglett.5b03543

  日期：2016.2.5

  A new and efficient approach for the synthesis of oxygen and nitrogen heterocycles by organoselenium catalysis has been developed. The exo-cyclization proceeded smoothly under mild conditions with good functional group tolerance and excellent regioselectivity. Mechanistic studies revealed that 1-fluoropyridinium triflate is key for oxidative cyclization.

  已经开发了一种通过有机硒催化合成氧和氮杂环的新的有效方法。所述外切-cyclization具有良好的官能团耐受性和优良的区位选择性温和的条件下顺利进行。机理研究表明，三氟甲磺酸1-氟吡啶鎓是氧化环化的关键。
• Enantioselective Cationic Polyene Cyclization vs Enantioselective Intramolecular Carbonyl−Ene Reaction
  作者：Yu-Jun Zhao、Bin Li、Li-Jun Serena Tan、Zhi-Liang Shen、Teck-Peng Loh

  DOI：10.1021/ja104119j

  日期：2010.8.4

  This paper describes highly efficient catalytic enantioselective cationic polyene cyclization and catalytic enantioselective intramolecular carbonyl-ene reaction in good to high yields with high enantioselectivities. The intimate relationship and mechanistic differences between the two enantioselective reactions were studied in detail. In addition, the cyclization products are versatile and useful building

  本文描述了高效催化对映选择性阳离子多烯环化和催化对映选择性分子内羰基-烯反应，产率高，对映选择性高。详细研究了两种对映选择性反应之间的密切关系和机理差异。此外，环化产物是天然产物和药物合成的通用且有用的构件。
• Stereocontrolled one-pot synthesis of cycloalkane derivatives possessing a quaternary carbon using allyl phenyl sulfone
  作者：Koichiro Ota、Takao Kurokawa、Etsuko Kawashima、Hiroaki Miyaoka

  DOI：10.1016/j.tet.2009.08.058

  日期：2009.10

  Stereocontrolled one-pot synthesis of cyclopentane derivatives possessing quaternary carbon using allyl phenyl sulfone and epoxyiodide was presented. Furthermore, application of this protocol to the synthesis of cycloalkane derivatives with different ring sizes was successful.

  提出了使用烯丙基苯基砜和环氧碘化物立体控制一锅合成具有季碳的环戊烷衍生物的方法。此外，该方案成功地用于合成具有不同环尺寸的环烷烃衍生物。
• Tandem carbonyl ene cyclization-cycloalkylation: a route to trifluoromethyl diterpenoids.
  作者：Ahmed Abouabdellah、Danièle Bonnet-Delpon

  DOI：10.1016/s0040-4020(01)89305-4

  日期：1994.1

  A new sequential carbonyl-ene cyclizatian/cycloalkylation of trifluoromethyl ketones catalyzed by aluminum Lewis acids is described. From ketone 1, the 4-CF3-4-OH cis-octahydrophenanthrene 6 is obtained in 50 % yield. From ketone 2, with MeAlCl(2) a total stereoselective route to the 4-CF3-trans-10-methyl podocarpatrienol 8 (90 % yield) has been found. These studies also exhibited some striking results in the stereochemical outcome of ene cyclizations.