(3E and 3Z)-2,2-dimethyl-4-phenyl-3-buten-1-ol

• 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: (3E and 3Z)-2,2-dimethyl-4-phenyl-3-buten-1-ol
• 英文别名: 2,2-dimethyl-4-phenylbut-3-en-1-ol
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: UVHMQPSWDYAKNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3E and 3Z)-2,2-dimethyl-4-phenyl-3-buten-1-ol 在 4-二甲氨基吡啶 、 高氯酸铵 、 (1,4,8,11-tetraazacyclotetradecane)nickel(II) perchlorate 、 高氯酸四乙基铵 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (1E and 1Z)-5-acetoxy-3,3-dimethyl-1-phenyl-1-butene
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e
• 作为产物：
  描述：

  4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 六氟异丙醇 、 1-(4-methoxy-3,5-dimethylpyridin-2-yl)-N-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-N-(pyridin-2-ylmethyl)methanamine 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 (3E and 3Z)-2,2-dimethyl-4-phenyl-3-buten-1-ol
  参考文献：
  名称：

  Radical-Organometallic Hybrid Reaction System Enabling Couplings between Tertiary-Alkyl Groups and 1-Alkenyl Groups

  摘要：

  Suzuki-Miyaura couplings of tertiary-alkyl moieties are accomplished in the presence of a copper catalyst, in which quaternary carbons possessing various functional groups can be synthesized via a radical reaction. Mechanistic studies revealed that 1-alkenylcopper(I) plays an important role in this coupling reaction. We expect that the radical-organometallic combined process will become one of the best options for the synthesis of quaternary carbons.

  DOI：

  10.1021/acscatal.8b01572

文献信息

• Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
  作者：Shenghan Teng、Malcolm E. Tessensohn、Richard D. Webster、Jianrong Steve Zhou

  DOI：10.1021/acscatal.8b02029

  日期：2018.8.3

  palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies

  据报道，钯催化的环状和非环状环氧化物的分子间Heck型反应均具有典型极性基团和酸性质子的耐受性。合适的烯烃包括苯乙烯，共轭二烯和一些缺电子的烯烃。在脂族末端环氧化物的反应中，开环选择性地在末端位置发生，并且环氧化物的立体中心被完全保留。机理研究为将环氧化合物原位转化为β-卤代醇，生成烷基自由基以及向烯烃中自由基加成作为关键步骤提供了证据。循环伏安法测定还原电位表明，在通过钯（0）络合物活化烷基碘的过程中，内球卤素的提取比外球单电子转移的可能性更大。
• Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis
  作者：Masataka Ihara、Akira Katsumata、Fumihito Setsu、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo951653e

  日期：1996.1.1

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.
• Radical-Organometallic Hybrid Reaction System Enabling Couplings between Tertiary-Alkyl Groups and 1-Alkenyl Groups
  作者：Kimiaki Nakamura、Reina Hara、Yusuke Sunada、Takashi Nishikata

  DOI：10.1021/acscatal.8b01572

  日期：2018.8.3

  Suzuki-Miyaura couplings of tertiary-alkyl moieties are accomplished in the presence of a copper catalyst, in which quaternary carbons possessing various functional groups can be synthesized via a radical reaction. Mechanistic studies revealed that 1-alkenylcopper(I) plays an important role in this coupling reaction. We expect that the radical-organometallic combined process will become one of the best options for the synthesis of quaternary carbons.