4-hexyl-1,2-dimethylcyclohexa-1,4-diene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 4-hexyl-1,2-dimethylcyclohexa-1,4-diene
• 化学式: C₁₄H₂₄
• 分子量: 192.345
• InChiKey: ZFXGFPHNBNORBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-辛炔 、 2,3-二甲基-1,3-丁二烯 在 9-borabicyclo[3.3.1]nonane dimer 作用下， 以 四氢呋喃 为溶剂， 反应 336.0h， 以65%的产率得到4-hexyl-1,2-dimethylcyclohexa-1,4-diene
  参考文献：
  名称：

  Catalysis by temporary covalent activation. A novel catalysis of unactivated Diels-Alder reactions

  摘要：

  Diels-Alder reactions of cis-2-chlorovinyltributylstannane are greatly accelerated by tbe presence of catalytic amounts of haloboranes. Mechanistic studies support a mechanism for the catalysis involving an intermediate boron-activated dienophile. A similar but simpler catalysis of Diels-Alder reactions of unactivated alkynes, via a hydroboration - Diels-Alder - dehydroboration mechanism, is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00584-4

文献信息

• Rhodium <i>N</i>-Heterocyclic Carbene-Catalyzed [4 + 2] and [5 + 2] Cycloaddition Reactions
  作者：Sang Ick Lee、Se Yeoun Park、Ji Hoon Park、Il Gu Jung、Soo Young Choi、Young Keun Chung、Bun Yeoul Lee

  DOI：10.1021/jo051685u

  日期：2006.1.1

  A rhodium complex of N-heterocyclic carbene (NHC) has been developed for intra- and intermolecular [4 + 2] and intramolecular [5 + 2] cycloaddition reactions. This is the first use of a transition-metal NHC complex in a Diels−Alder-type reaction. For the intramolecular [4 + 2] cycloaddition reactions, all the dienynes studied were converted to their corresponding cycloadducts in 91−99% yields within

  N的铑配合物-杂环卡宾（NHC）已开发用于分子内和分子间[4 + 2]和分子内[5 + 2]环加成反应。这是在Diels-Alder型反应中首次使用过渡金属NHC配合物。对于分子内[4 + 2]环加成反应，所有研究的二烯在10分钟内以91-99％的产率转化为其相应的环加合物。此外，在15-20°C下，分子内[4 + 2]环加成反应已获得1900次的转换。对于分子间的[4 + 2]环加成反应，可获得相应环加成产物的高收率（71-99％）。反应时间和收率高度依赖于二烯和亲二烯体。对于分子内[5 + 2]环加成反应，在10分钟内，所有研究的炔烃乙烯基环丙烷均以91-98％的产率转化为其相应的环加合物。然而，该催化体系对于分子间[5 + 2]环加成反应无效。
• Catalysis by temporary covalent activation. A novel catalysis of unactivated Diels-Alder reactions
  作者：Daniel A. Singleton、Shun-Wang Leung、Jose P. Martinez、Yu-Kai Lee

  DOI：10.1016/s0040-4039(97)00584-4

  日期：1997.5

  Diels-Alder reactions of cis-2-chlorovinyltributylstannane are greatly accelerated by tbe presence of catalytic amounts of haloboranes. Mechanistic studies support a mechanism for the catalysis involving an intermediate boron-activated dienophile. A similar but simpler catalysis of Diels-Alder reactions of unactivated alkynes, via a hydroboration - Diels-Alder - dehydroboration mechanism, is also described. (C) 1997 Elsevier Science Ltd.
• Highly Efficient Intra- and Intermolecular [4 + 2] Cycloaddition Reaction Catalyzed by Rhodium Complex
  作者：Se-Jung Paik、Seung Uk Son、Young Keun Chung

  DOI：10.1021/ol990169l

  日期：1999.12.1

  [GRAPHICS]A cationic Rh(I) complex, [(eta(6)-C10H8)Rh(cod)]BF4, has been found to be a quite useful catalytic system for both the intermolecular [4 + 2] cycloaddition reaction of 1,3-dienes with nonactivated acetylenes and the intramolecular [4 + 2] cycloaddition of dienyne under very mild reaction conditions (CH2Cl2, 15 degrees C, 15 min).