2-methylnaphthalene-1-methanol | 1706-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methylnaphthalene-1-methanol
• 英文别名: α-methyl-1-naphthalenometanol；1-hydroxymethyl-2-methylnaphthalene；2-methyl-1-hydroxymethylnaphthalene；2-Methyl-1-hydroxymethyl-naphthalin；1¹-Oxy-1.2-dimethyl-naphthalin；1-Hydroxymethyl-2-methyl-naphthalin；(2-Methyl-naphthyl-(1))-carbinol；(2-Methyl-[1]naphthyl)-methanol；methyl-1-naphthalenemethanol；α-methyl-1-naphthyl-methanol；2-methylnaphthyl carbinol；(2-Methylnaphthalen-1-yl)methanol
• CAS: 1706-15-6
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: HZFBCINSFDDVLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-methylnaphthalene-1-methanol 在 氢溴酸 、 溶剂黄146 作用下， 生成 1-(溴甲基)-2-甲基萘
  参考文献：
  名称：

  Ziegler; Tiemann, Chemische Berichte, 1922, vol. 55, p. 3414

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-双(溴甲基)-萘 在 2,6-二甲基吡啶 、 sodium hydroxide 、 lithium 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.25h， 生成 2-methylnaphthalene-1-methanol
  参考文献：
  名称：

  Regiochemistry in the reductive opening of phthalan derivatives

  摘要：

  The lithiation of phthalan derivatives 4, 9 and 12 with an excess of lithium in the presence of a catalytic amount of 4,4'-ditert-butylbiphenyl (DTBB) in THF at -78 degrees C gives dianionic intermediates 5, 10 and 13, respectively, which by reaction with different electrophiles [H2O, tau-BuCHO, Me2CO, (EtO)(2)CO] at the same temperature, followed by hydrolysis, leads to regioselective functionalised naphthalenes 7, and biphenyls 11 and 14. The reductive opening takes place with high or total regioselectivity and can be explained considering the electron density in the dianion or in the radical anion, which are formed previous to the carbon-oxygen bond excision. The lithiation of the dihydrofurophthalan derivative 18 with the same reaction mixture but at higher temperature (0 degrees C) leads to intermediates 19 and 20, resulting from a single and a double reductive cleavage, respectively, which after addition of H2O and benzaldehyde as electrophiles gives a mixture of compounds 21 and 22. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.069

文献信息

• Facile reductive coupling of benzylic halides with ferrous oxalate dihydrate
  作者：Jitender M. Khurana、Sushma Chauhan、Golak C. Maikap

  DOI：10.1039/b211792d

  日期：2003.5.15

  Facile reductive coupling of benzylic halides is reported with ferrous oxalate dihydrate in DMF or HMPA under nitrogen atmosphere at 155–160 °C. The coupling is proposed to proceed by two successive oxidative additions of benzylic halides to ferrous oxalate to give an intermediate organoiron complex which undergoes concerted dimerization to give the corresponding reductively coupled dimers in high yields.

  报道称，在氮气气氛下，使用二水合草酸亚铁在DMF或HMPA中，于155-160°C的温度下，可以轻松实现苄基卤化物的还原耦合反应。该耦合反应被认为是通过苄基卤化物对草酸亚铁的两次连续氧化加成，生成一种中间体有机铁配合物，该配合物随后经历协同二聚反应，以高产率得到相应的还原耦合二聚体。
• Peri-methanoarenes by thermolysis of [methoxy(arenyl)methyl]trimethylsilanes
  作者：T.A. Engler、H. Shechter

  DOI：10.1016/s0040-4039(00)87439-0

  日期：——

  Practical synthesis of varied peri-methanoarenes have been developed.

  已经开发了各种环甲基芳烃的实用合成方法。
• Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates
  作者：Masaaki Komatsuda、Kei Muto、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.8b01807

  日期：2018.7.20

  Dearomative C–C bond formation of benzyl phosphates has been developed. In the presence of a palladium/PAr3 catalyst, benzyl phosphates reacted with allyl borates to generate the allylated product in a dearomative fashion. The resulting dearomatized molecules were successfully derivatized by Simmons–Smith cyclopropanation and oxidation.

  已经开发出苄基磷酸的脱芳香族C–C键形成。在钯/ PAr 3催化剂的存在下，磷酸苄酯与硼酸烯丙酯反应，以脱芳族方式生成烯丙基化产物。产生的脱芳烃分子已通过Simmons-Smith环丙烷化和氧化作用成功衍生。
• Pd-catalyzed allylative dearomatisation using Grignard reagents
  作者：Cosimo Boldrini、Syuzanna R. Harutyunyan

  DOI：10.1039/d1cc05609c

  日期：——

  naphthyl halides is shown to be feasible by employing Grignard reagents. The high reactivity of the nucleophile allows for fast reactions and low catalyst loading, while a plethora of successfully substituted compounds illustrate the broad scope. Five membered heteroaromatic compounds are also demonstrated to be reactive under similar conditions.

  通过使用格氏试剂，钯催化的萘基卤化物的烯丙基化脱芳构化被证明是可行的。亲核试剂的高反应活性允许快速反应和低催化剂负载，而大量成功取代的化合物说明了广泛的范围。五元杂芳族化合物也被证明在类似条件下具有反应性。
• Pd-catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane
  作者：Yuki Kayashima、Masaaki Komatsuda、Kei Muto、Junichiro Yamaguchi

  DOI：10.1246/cl.200216

  日期：2020.7.5

  A dearomative C4-allylation of benzyl ammoniums with allyltributylstannane by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzyli...

  描述了在钯催化下苄基铵与烯丙基三丁基锡烷的脱芳基 C4-烯丙基化反应。三芳基膦连接的钯催化剂，能够裂解苄基...