(Z)-1-(2,8-nonadienyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (Z)-1-(2,8-nonadienyl)piperidine
• 英文别名: 1-[(Z)-2,8-nonadienyl]piperidine；1-[(2Z)-nona-2,8-dienyl]piperidine
• 化学式: C₁₄H₂₅N
• 分子量: 207.359
• InChiKey: ISIKHFAJYPDVGE-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (Z)-2,8-nonadien-1-ol 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 亚磷酸三苯酯 作用下， 反应 3.0h， 生成 (Z)-1-(2,8-nonadienyl)piperidine
  参考文献：
  名称：

  Complete Retention of Z Geometry in Allylic Substitution Catalyzed by an Iridium Complex

  摘要：

  [GRAPHICS]The Z geometry of methyl (Z)-3-monosubstituted-2-alkenyl carbonate was completely retained in iridium complex-catalyzed allylic amination. The reaction of methyl (Z)-2-nonenyl carbonate with piperidine in the presence of a catalytic amount of [Ir(COD)Cl](2) and P(OPh)(3) at 50 degrees C for 2 h gave a 98:2 mixture of (Z)-1-(2-nonenyl)piperidine and 1-(1-n-hexyl-2-propenyl)piperidine in 86% yield, No E isomer was obtained. Various (Z) allylic amines were obtained in 91-100% selectivity by allylic amination of methyl (Z) 3-monosubstituted-2-alkenyl carbonate.

  DOI：

  10.1021/ol990033n

文献信息

• Iridium Complex-Catalyzed Allylic Amination of Allylic Esters
  作者：Ryo Takeuchi、Naoki Ue、Keisuke Tanabe、Kengo Yamashita、Norihito Shiga

  DOI：10.1021/ja0112036

  日期：2001.10.1

  Iridium complex-catalyzed allylic amination of allylic carbonates was studied. The solvent strongly affected the catalytic activity. The use of a polar solvent such as EtOH is essential for obtaining the products in high yield, The reaction of (E)-3-substituted-2-propenyl carbonate and 1-substituted-2-propenyl carbonate with pyrrolidine in the presence of a catalytic amount of [Ir(COD)Cl](2) and P(OPh)(3) (P/Ir = 2) gave a branch amine with up to 99% selectivity. Both secondary and primary amines could be used for this reaction. When a primary amine was used, selective monoallylation occurred. No diallylation product was obtained. The reaction of 1,1-disubstituted-2 propenyl acetate with amines exclusively gave an alpha,alpha -disubstituted allylic amine. This reaction provides an alternative route to the addition of an organometallic reagent to ketimines. for the preparation of such amines. The reaction of (Z)-3-substituted-2-propenyl carbonate with amines gave (Z)-linear amines with up to 100% selectivity. In all cases, no (E)-linear amine was obtained. The selectivities described here have not been achieved in similar palladium complex-catalyzed reactions.
• Complete Retention of <i>Z</i> Geometry in Allylic Substitution Catalyzed by an Iridium Complex
  作者：Ryo Takeuchi、Norihito Shiga

  DOI：10.1021/ol990033n

  日期：1999.7.1

  [GRAPHICS]The Z geometry of methyl (Z)-3-monosubstituted-2-alkenyl carbonate was completely retained in iridium complex-catalyzed allylic amination. The reaction of methyl (Z)-2-nonenyl carbonate with piperidine in the presence of a catalytic amount of [Ir(COD)Cl](2) and P(OPh)(3) at 50 degrees C for 2 h gave a 98:2 mixture of (Z)-1-(2-nonenyl)piperidine and 1-(1-n-hexyl-2-propenyl)piperidine in 86% yield, No E isomer was obtained. Various (Z) allylic amines were obtained in 91-100% selectivity by allylic amination of methyl (Z) 3-monosubstituted-2-alkenyl carbonate.