2-neopentylnaphthalene | 61760-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-neopentylnaphthalene
• 英文别名: 2-Neopentylnaphthalin；2-(2,2-Dimethylpropyl)naphthalene
• CAS: 61760-11-0
• 化学式: C₁₅H₁₈
• 分子量: 198.308
• InChiKey: SSWJWQZWRQOCGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  meso-2,2,5,5-tetramethyl-3,4-di-2-naphthylhexane 在 9,10-二氢蒽 作用下， 以 均三甲苯 为溶剂， 生成 2-neopentylnaphthalene
  参考文献：
  名称：

  Herberg, Clemens; Peyman, Anuschirwan; Noelke, Margot, Liebigs Annalen, 1995, # 5, p. 881 - 884

  摘要：

  DOI：

文献信息

• Nickel-Catalyzed Reductive Cleavage of Carbon–Oxygen Bonds in Anisole Derivatives Using Diisopropylaminoborane
  作者：Takuya Igarashi、Akira Haito、Naoto Chatani、Mamoru Tobisu

  DOI：10.1021/acscatal.8b02009

  日期：2018.8.3

  of a methoxy group on an aromatic ring allows this group to be used as a traceless activating and directing group for aromatic functionalization reactions. Although several catalytic methods for the reductive cleavage of anisole derivatives have been reported, all are applicable only to π-extended aryl ethers, such as naphthyl and biphenyl ethers, while monocyclic aryl ethers cannot be reduced. Herein

  芳族环上甲氧基的催化除去使得该基团可用作芳族官能化反应的无痕活化和导向基团。尽管已经报道了几种用于苯甲醚衍生物的还原裂解的催化方法，但是所有方法仅适用于π-延伸的芳基醚，例如萘基和联苯醚，而单环芳基醚不能被还原。在本文中，我们报道了使用二异丙基氨基硼烷作为还原剂的镍催化的芳基醚中C–O键的还原裂解反应。与以前报道的方法不同，这种还原剂可在范围更广的芳基醚底物（包括带有各种官能团的单环和杂环醚）中有效地降低C-O键。
• Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C–O Bond Cleavage
  作者：Mamoru Tobisu、Tsuyoshi Takahira、Naoto Chatani

  DOI：10.1021/acs.orglett.5b02200

  日期：2015.9.4

  Nickel-catalyzed cross-coupling of methoxyarenes with alkyl Grignard reagents, which involves the cleavage of the C(aryl)–OMe bond, has been developed. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand allows the introduction of a variety of alkyl groups, including Me, Me3SiCH2, ArCH2, adamantyl, and cyclopropyl. The method can also be used for the alkylative elaboration of complex molecules

  已经开发了镍催化的甲氧基芳烃与烷基格氏试剂的交叉偶联，这涉及到C（芳基）-OMe键的裂解。使用1，3-二环己基咪唑-2-亚烷基作为配体允许引入各种烷基，包括Me，Me 3 SiCH 2，ArCH 2，金刚烷基和环丙基。该方法还可用于带有C（芳基）–OMe键的复杂分子的烷基化修饰。
• Visible-Light-Promoted Nickel-Catalyzed Cross-Coupling of Alkyltitanium Alkoxides with Aryl and Alkenyl Halides
  作者：Andrei A. Leushukou、Anastasiya V. Krech、Alaksiej L. Hurski

  DOI：10.1021/acs.orglett.2c02428

  日期：2022.9.2

  alkyltitanium alkoxides generated in situ from Grignard reagents and Ti(OiPr)4 undergo a photocatalyst-free nickel-catalyzed cross-coupling with organic halides upon irradiation with blue light. Mechanistic studies suggested that the reaction proceeds through radical intermediates formed by photochemical decomposition of the alkyltitanium reagents. Various aryl, heteroaryl, and vinyl halides were efficiently

  在这里，我们报告了由格氏试剂和 Ti(O i Pr) 4原位生成的烷基钛醇盐在蓝光照射下与有机卤化物发生无光催化剂镍催化的交叉偶联。机理研究表明，反应通过烷基钛试剂的光化学分解形成的自由基中间体进行。各种芳基、杂芳基和乙烯基卤化物在报告的条件下被有效地烷基化，包括那些含有酯和酰胺基团的。
• Nickel-electrocatalysed C(sp3)–C(sp3) cross-coupling of unactivated alkyl halides
  作者：Pengfei Li、Zile Zhu、Chengcheng Guo、Guangsheng Kou、Siyi Wang、Pengfei Xie、Dengke Ma、Tian Feng、Yanwei Wang、Youai Qiu

  DOI：10.1038/s41929-024-01118-3

  日期：——

  reactivity and selectivity control of unactivated alkyl halides. Here we report a general strategy for electrochemical cross-electrophile coupling of unactivated alkyl halides under nickel catalysis. The highly selective electrochemical cross-electrophile coupling process was carried out in an operationally simple manner with high selectivity, setting the stage for the challenging C(sp3)–C(sp3) bonds

  C( sp 3 )–C( sp 3 ) 连接在天然产物、药物和有机化合物中无疑是重要的。电化学交叉亲电子试剂与多种可用的卤代烷偶联是构建 C( sp 3 )–C( sp 3 ) 键的一种有吸引力且有用的策略，尽管在之前的报道中只能在活化的卤代烷上看到成功，由于未活化的烷基卤化物的反应性和选择性控制面临巨大挑战。在这里，我们报告了在镍催化下未活化的烷基卤化物电化学交叉亲电子偶联的一般策略。高选择性电化学交叉亲电子偶联过程以操作简单的方式进行，具有高选择性，为具有挑战性的C( sp 3 )–C( sp 3 )键结构与多功能未活化的烷基卤化物奠定了基础，包括交叉-伯-伯卤化物、伯-仲卤化物、伯-叔卤化物和仲-仲卤化物的偶联，具有高选择性和优异的官能团相容性。多样化的产品以及生物相关化合物的各种后期修饰，证明了其在有机合成和药物化学中的潜在用途。
• Thermochromic Furofurans. IV. Approach to the synthesis of bridgehead substituted furo[3,2-b]furans and side products of McMurry reactions
  作者：Hartmut Laatsch、Antti Talvitie、Andreas Kral、Bernd-Peter Ernst、Mathias Noltemeyer

  DOI：10.1002/prac.19963380127

  日期：——

  Substituted dihydroxystilbenes 2 are suitable starting materials for the synthesis of photochromic systems derived from 3/4. Attempts to couple the naphthones 8a-8e by the McMurry reaction with TiCl3/LiAlH4 yielded mainly reduction products such as 8f, g or 9. However, the furofuran 3b was isolated when using the zinc-copper couple for reduction. The helicene 11 was formed as an unexpected byproduct in the McMurry reaction of the pivaloylnaphthalene 8d.