2,2-diphenylhepta-5,6-dien-1-ol | 906542-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-diphenylhepta-5,6-dien-1-ol
• CAS: 906542-59-4
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: PWAJBWWGLASXCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  2,2-diphenylhepta-5,6-dien-1-ol 在 silver hexafluoroantimonate 、 氯[2-(二叔丁基磷)二苯基]金 、 silver(I) 4-methylbenzenesulfonate 、 三乙胺 作用下， 以 二氯甲烷-D2 、 甲苯 为溶剂， 反应 10.0h， 生成 (methyl-2 propene-1 yl)-2 tetrahydrofuranne
  参考文献：
  名称：

  取代，环大小和抗衡离子对金催化的烯类分子内氢烷氧基化反应中生成的中间体的影响。

  摘要：

  The reaction of 2,2-diphenylhepta-4,5-dien-1-ol (4) with (L)AuOTs [L = P(t-Bu)(2)0-biphenyl] and the Ph reactions of 2,2-diphenylhepta-5,6-dien-l-ol (10) with either (L)AuOTs or (L)AuCl/AgSbF6 have been investigated. For both substrates, the mono(gold) vinyl complexes generated via C-O bond formation have been independently synthesized, and the protodeauration behavior has been investigated. Analysis of the reaction of 4 with (L)AuOTs supported a mechanism involving rapid and reversible C-O bond formation followed by rate limiting and stereochemically determining protodeauration. Analysis of the reaction of 10 with (L)AuOTs was in accord with irreversible C-O bond formation followed by rapid auration of the resulting mono(gold) vinyl complex. In comparison, analysis of the reaction of 10 with (L)AuCl/AgSbF6 pointed to a mechanism involving rate-limiting C-O bond formation followed by rapid protodeauration of the resulting mono(gold) vinyl complex without competitive auration.

  DOI：

  10.1021/acs.organomet.6b00306
• 作为产物：
  描述：

  methyl 2,2-diphenylhex-5-ynoate 在 lithium aluminium tetrahydride 、 二异丙胺 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 生成 2,2-diphenylhepta-5,6-dien-1-ol
  参考文献：
  名称：

  用于与碳、氮和氧亲核试剂对艾伦烯进行分子内外加氢官能化的高活性 Au(I) 催化剂

  摘要：

  (2,2-二苯基-4,5-己二烯基)氨基甲酸苄酯 (4) 与 Au[P(t-Bu)2(o-biphenyl)]Cl (2) 和 AgOTf 的 1:1 催化混合物反应5 mol%) 在二恶烷中在 25 摄氏度下 45 分钟导致 4,4-二苯基-2-乙烯基吡咯烷-1-羧酸苄酯 (5) 的分离，产率为 95%。Au(I) 催化的 N-烯丙氨基甲酸酯的分子内加氢胺化耐受烷基和烯基碳原子处的取代，并且对于哌啶衍生物的形成是有效的。γ-羟基和δ-羟基丙二烯也在室温下几分钟内经历了金催化的分子内加氢烷氧基化，以高产率和高外选择性形成相应的氧杂环。2-烯基吲哚在室温下几分钟内经历金催化的分子内加氢芳基化，以良好的产率形成4-乙烯基四氢咔唑。

  DOI：

  10.1021/ja062045r

文献信息

• Gold(I)-Catalyzed Intramolecular Enantioselective Hydroalkoxylation of Allenes
  作者：Zhibin Zhang、Ross A. Widenhoefer

  DOI：10.1002/anie.200603260

  日期：2007.1
• Highly Active Au(I) Catalyst for the Intramolecular <i>e</i><i>xo</i>-Hydrofunctionalization of Allenes with Carbon, Nitrogen, and Oxygen Nucleophiles
  作者：Zhibin Zhang、Cong Liu、Robert E. Kinder、Xiaoqing Han、Hua Qian、Ross A. Widenhoefer

  DOI：10.1021/ja062045r

  日期：2006.7.19

  Au-catalyzed intramolecular hydroalkoxylation within minutes at room temperature to form the corresponding oxygen heterocycles in good yield with high exo-selectivity. 2-Allenyl indoles underwent Au-catalyzed intramolecular hydroarylation within minutes at room temperature to form 4-vinyl tetrahydrocarbazoles in good yield. Au-catalyzed cyclization of N-allenyl carbamates, allenyl alcohols, and 2-allenyl

  (2,2-二苯基-4,5-己二烯基)氨基甲酸苄酯 (4) 与 Au[P(t-Bu)2(o-biphenyl)]Cl (2) 和 AgOTf 的 1:1 催化混合物反应5 mol%) 在二恶烷中在 25 摄氏度下 45 分钟导致 4,4-二苯基-2-乙烯基吡咯烷-1-羧酸苄酯 (5) 的分离，产率为 95%。Au(I) 催化的 N-烯丙氨基甲酸酯的分子内加氢胺化耐受烷基和烯基碳原子处的取代，并且对于哌啶衍生物的形成是有效的。γ-羟基和δ-羟基丙二烯也在室温下几分钟内经历了金催化的分子内加氢烷氧基化，以高产率和高外选择性形成相应的氧杂环。2-烯基吲哚在室温下几分钟内经历金催化的分子内加氢芳基化，以良好的产率形成4-乙烯基四氢咔唑。
• Effect of Substitution, Ring Size, and Counterion on the Intermediates Generated in the Gold-Catalyzed Intramolecular Hydroalkoxylation of Allenes
  作者：Rachel E. M. Brooner、Timothy J. Brown、Mark A. Chee、Ross A. Widenhoefer

  DOI：10.1021/acs.organomet.6b00306

  日期：2016.6.13

  The reaction of 2,2-diphenylhepta-4,5-dien-1-ol (4) with (L)AuOTs [L = P(t-Bu)(2)0-biphenyl] and the Ph reactions of 2,2-diphenylhepta-5,6-dien-l-ol (10) with either (L)AuOTs or (L)AuCl/AgSbF6 have been investigated. For both substrates, the mono(gold) vinyl complexes generated via C-O bond formation have been independently synthesized, and the protodeauration behavior has been investigated. Analysis of the reaction of 4 with (L)AuOTs supported a mechanism involving rapid and reversible C-O bond formation followed by rate limiting and stereochemically determining protodeauration. Analysis of the reaction of 10 with (L)AuOTs was in accord with irreversible C-O bond formation followed by rapid auration of the resulting mono(gold) vinyl complex. In comparison, analysis of the reaction of 10 with (L)AuCl/AgSbF6 pointed to a mechanism involving rate-limiting C-O bond formation followed by rapid protodeauration of the resulting mono(gold) vinyl complex without competitive auration.