8-methyl-nona-1,7-diene | 90975-99-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 8-methyl-nona-1,7-diene
• 英文别名: 8-methylnona-1,7-diene；8-Methyl-nonadien-1,7；1,7-Nonadiene, 8-methyl-
• CAS: 90975-99-8
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: VMEDJHVTTJXKCN-UHFFFAOYSA-N

物化性质

• 沸点：
  162.5±10.0 °C(Predicted)
• 密度：
  0.759±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  8-methyl-nona-1,7-diene 生成 o-menth-8-ene
  参考文献：
  名称：

  A Study of the Thermal Cyclization of 1,7-Alkadienes and Monocyclic Dienes¹

  摘要：

  DOI：

  10.1021/jo01053a014
• 作为产物：
  描述：

  (hept-6-enyl)-triphenylphosphonium bromide 、 丙酮 在 正丁基锂 作用下， 以 正己烷 、 二甲基亚砜 为溶剂， 反应 16.0h， 以74%的产率得到8-methyl-nona-1,7-diene
  参考文献：
  名称：

  Cycloisomerization of Dienes with Carbophilic Lewis Acids:  Mimicking Terpene Biosynthesis with Pt(II) Catalysts

  摘要：

  Dicationic Pt(II) complexes containing triphosphine pincer ligands are excellent catalysts for the cycloisomerization of 1,6- and 1,7-dienes into bicyclopropane carbocycles. In analogy to the biosynthetic route to these monoterpene-like compounds, carbocation intermediates are proposed and supported by trapping experiments. Reactivation of the trapped intermediates indicates that cation generation by C-C bond formation is both rapid and reversible.

  DOI：

  10.1021/ol051277c

文献信息

• Branched‐Selective Direct α‐Alkylation of Cyclic Ketones with Simple Alkenes
  作者：Dong Xing、Xiaotian Qi、Daniel Marchant、Peng Liu、Guangbin Dong

  DOI：10.1002/anie.201900301

  日期：2019.3.22

  Herein, we describe an intermolecular direct branched‐selective α‐alkylation of cyclic ketones with simple alkenes as the alkylation agents. Through an enamine‐transition metal cooperative catalysis mode, the α‐alkylation is realized in an atom‐ and step‐economic manner with excellent branched selectivity for preparing β‐branched ketones. Employment of a pair of bulky Brønsted acid and base as additives

  在本文中，我们描述了以简单烯烃作为烷基化剂的环状酮的分子间直接支链选择性α-烷基化。通过烯胺-过渡金属的协同催化模式，α-烷基化反应可在原子经济和分步经济的方式下实现，并具有出色的支化选择性，可制备β-支化的酮。使用一对笨重的布朗斯台德酸和碱作为添加剂有助于提高效率。已获得有希望的对映选择性（74％  ee）。实验和计算机制研究表明，通过烯烃迁移插入Ir-C键然后CH-H还原消除的途径涉及高支化选择性。
• Modular Catalysts for Diene Cycloisomerization:  Rapid and Enantioselective Variants for Bicyclopropane Synthesis
  作者：Jeremy A. Feducia、Alison N. Campbell、Michael Q. Doherty、Michel R. Gagné

  DOI：10.1021/ja064335d

  日期：2006.10.1

  Deconstructing the tridentate (triphos)Pt(II) first-generation catalysts into mixed diphosphine/monophosphine combinations (P2P) has led to new, more active catalysts for the cycloisomerization of 1,6-, and 1,7-dienes into bicyclo-[3.1.0] and -[4.1.0] products. When the diphosphine was the small bite angle dppm, reaction rates were similar to 20-fold faster than with triphos, although reaction rates and diastereoselectivities were also sensitive to the monophosphine (PMe3 being optimal for rate, PPh3 being optimal for selectivity). When the diphosphine was xyl-BINAP or SEGPHOS, the catalysts were enantioselective, and enantio-ratios up to 98:2 were observed. Both sets of catalysts showed enhanced functional group tolerance in comparison to the original (triphos)Pt2+ catalyst. X-ray structures for both precatalysts are also reported.
• Cycloisomerization of Dienes with Carbophilic Lewis Acids:  Mimicking Terpene Biosynthesis with Pt(II) Catalysts
  作者：William D. Kerber、Michel R. Gagné

  DOI：10.1021/ol051277c

  日期：2005.7.1

  Dicationic Pt(II) complexes containing triphosphine pincer ligands are excellent catalysts for the cycloisomerization of 1,6- and 1,7-dienes into bicyclopropane carbocycles. In analogy to the biosynthetic route to these monoterpene-like compounds, carbocation intermediates are proposed and supported by trapping experiments. Reactivation of the trapped intermediates indicates that cation generation by C-C bond formation is both rapid and reversible.
• A Study of the Thermal Cyclization of 1,7-Alkadienes and Monocyclic Dienes¹
  作者：William D. Huntsman、Philip C. Lang、Norman L. Madison、David A. Uhrick

  DOI：10.1021/jo01053a014

  日期：1962.6