1-(chloro(p-tolyl)methyl)naphthalene | 1195262-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(chloro(p-tolyl)methyl)naphthalene
• 英文别名: 4-(chloro(p-tolyl)methyl)naphthalene；1-[Chloro-(4-methylphenyl)methyl]naphthalene
• CAS: 1195262-09-9
• 化学式: C₁₈H₁₅Cl
• mdl: MFCD18575895
• 分子量: 266.77
• InChiKey: UYXVDUMPEFDUFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.111
• 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：

  吲哚 、 1-(chloro(p-tolyl)methyl)naphthalene 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到
  参考文献：
  名称：

  Pd(0)-catalyzed benzylation of indole through η3-benzyl palladium intermediate

  摘要：

  An efficient method has been developed for the Pd(0)-catalyzed benzylation of indoles, which occurred with exclusive regioselectivity. When this reaction was performed in the presence of Pd(PPh3)(4), it provided access to a broad range of substituted indoles bearing diarylmethanes at their 3-position in 90%-99% yields under mild conditions. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s1872-2067(14)60191-1
• 作为产物：
  描述：

  1-溴代萘 在 氯化亚砜 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(chloro(p-tolyl)methyl)naphthalene
  参考文献：
  名称：

  Palladium-catalyzed C–H dimethylamination of 1-chloromethyl naphthalenes with N,N-dimethylformamide as the dimethyl amino source

  摘要：

  用 DMF 对 1-氯甲基萘进行远程 C-H 二甲基化。

  DOI：

  10.1039/d3ob00600j

文献信息

• Palladium-Catalyzed Ligand-Controlled Regioselective Nucleophilic Aromatic Substitution of 1-(Chloromethyl)naphthalenes with Arylacetonitriles
  作者：Sheng Zhang、Yoshinori Yamamoto、Ming Bao

  DOI：10.1021/acs.joc.8b02343

  日期：2018.11.16

  palladium-catalyzed reaction of 1-(chloromethyl)naphthalenes 1 with (hetero)arylacetonitriles 2 gives either para- or ortho-acylated naphthalenes (3 or 4) in good to high yields. The regioselectivity can be controlled by the ligand of a palladium catalyst. A sterically bulky ligand, tBuPPh2, affords para-acylated products 3, whereas a sterically less bulky ligand, Me2PPh, provides ortho-acylated products 4. Further

  的1-（氯甲基）钯催化反应萘1与（杂）arylacetonitriles 2给出或者对-或邻位-acylated萘（3或4以良好至高产率）。区域选择性可以通过钯催化剂的配体来控制。在空间上体积大的配体，t BuPPh 2，提供对酰化产物3，而在空间上体积较小的配体，Me 2 PPh，提供邻位酰化产物4。此外，直接替代产品5尽管在通常的亲核取代中，在苄基位置上的这种反应是有利的，但是基本上没有获得在苄基位置上的R 2的反应。在本文中，它揭示了在benzylpalladium中间可以通过不同的方式进行反应（η 3 -benzylpalladium中间或η 1 -benzylpalladium中间体）在亲核芳族取代。除了令人感兴趣的机理方面，本反应为广泛的二芳基酮提供了简便的合成方法，其中某些二芳基酮不能通过先前已知的方法容易地获得。
• Regioselective control using a catalyst switch in the reaction of diarylmethyl chlorides with allyltributylstannane
  作者：Bo Peng、Xiujuan Feng、Xin Zhang、Liyun Ji、Ming Bao

  DOI：10.1016/j.tet.2010.06.019

  日期：2010.8

  is described. The reaction pathway (allylative dearomatization vs cross-coupling) can be easily controlled using different catalysts. When reactions are performed in the presence of Pd2(dba)3 and PPh3, allylative dearomatization proceeds to provide satisfactory yield of the desired products. However, when Cy3P·HBF4 is employed as a catalyst instead of palladium, a Stille-type cross-coupling reaction

  描述了在二芳基甲基氯化物5a与烯丙基三丁基锡反应中的区域选择性控制。可以使用不同的催化剂轻松控制反应途径（烯丙基脱芳香化与交叉偶联）。当在Pd 2（dba）3和PPh 3的存在下进行反应时，进行烯丙基脱芳构作用以提供所需产物的令人满意的产率。然而，当使用Cy 3 P·HBF 4代替钯作为催化剂时，仅进行斯蒂勒型交叉偶联反应，以提供优异的相应产物收率。
• Palladium-Catalyzed Amination of Chloromethylnaphthalene and Chloromethylanthracene Derivatives with Various Amines
  作者：Sheng Zhang、Yi Wang、Xiujuan Feng、Ming Bao

  DOI：10.1021/ja300164d

  日期：2012.3.28

  Palladium-catalyzed amination of chloromethylnaphthalene and chloromethylanthracene derivatives to produce naphthylamines and anthrylamines in satisfactory to good yields has been developed. The unprecedented amination reactions proceeded smoothly under mild conditions in the presence of Pd(PPh3)(4) as a catalyst.
• Nucleophilic Dearomatization of Chloromethyl Naphthalene Derivatives via η³-Benzylpalladium Intermediates: A New Strategy for Catalytic Dearomatization
  作者：Bo Peng、Sheng Zhang、Xiaoqiang Yu、Xiujuan Feng、Ming Bao

  DOI：10.1021/ol2023278

  日期：2011.10.7

  Palladium-catalyzed nucleophilic dearomatization of chloromethyl naphthalene derivatives to produce ortho- or pare-substituted carbocycles in satisfactory to excellent yields has been developed. The unprecedented dearomatization reactions proceeded smoothly under mild conditions via eta(3)-benzylpalladium Intermediates.
• Pd(0)-catalyzed benzylation of indole through η3-benzyl palladium intermediate
  作者：Zheng-Le Zhao、Qing Gu、Xin-Yan Wu、Shu-Li You

  DOI：10.1016/s1872-2067(14)60191-1

  日期：2015.1

  An efficient method has been developed for the Pd(0)-catalyzed benzylation of indoles, which occurred with exclusive regioselectivity. When this reaction was performed in the presence of Pd(PPh3)(4), it provided access to a broad range of substituted indoles bearing diarylmethanes at their 3-position in 90%-99% yields under mild conditions. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.