(S)-2-(1-(4-methoxyphenyl)ethyl)naphthalene | 1424035-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-(1-(4-methoxyphenyl)ethyl)naphthalene
• 英文别名: 2-[(1S)-1-(4-methoxyphenyl)ethyl]naphthalene
• CAS: 1424035-17-5
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: XSYRATCRMLMRKA-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-(-)-1-(2-萘基)乙醇 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 (S)-2-(1-(4-methoxyphenyl)ethyl)naphthalene
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes

  摘要：

  We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.

  DOI：

  10.1021/ja312087x

文献信息

• Nickel-Catalyzed Asymmetric Hydroarylation of Vinylarenes: Direct Enantioselective Synthesis of Chiral 1,1-Diarylethanes
  作者：Hai N. Tran、Russell W. Burgett、Levi M. Stanley

  DOI：10.1021/acs.joc.0c02556

  日期：2021.3.5

  The enantioselective hydroarylation of vinylarenes catalyzed by a chiral, non-racemic nickel catalyst is presented as a facile method to generate chiral 1,1-diarylethanes. These reactions proceed via formation of a chiral, non-racemic nickel benzyl intermediate. Transmetalation with arylboron nucleophiles and subsequent reductive elimination enable the formation of a variety of chiral 1,1-diarylethanes

  介绍了一种通过手性，非外消旋镍催化剂催化的乙烯基芳烃的对映选择性加氢芳基化反应，是一种易于制备手性1,1-二芳基乙烷的方法。这些反应通过形成手性，非外消旋的苄基镍中间体。用芳基硼亲核试剂进行重金属化并随后进行还原性消除，使得能够形成多种手性的1,1-二芳基乙烷。由含给电子取代基的芳基硼酸反应生成的1,1-二芳基乙烷产物的ee通常大于90％，而由含吸电子基团的芳基硼酸反应生成的1,1-二芳基乙烷的生成量通常较小。超过80％ee。这些结果与芳基硼亲核试剂的重金属化速率一致，芳基硼亲核试剂在这些氢芳基化反应的对映选择性中起关键作用。这种机械的见解导致了新反应的发展。芳基硼酸与乙烯基芳烃的-戊基羟基乙酸酯，其基于增加的重金属化速率而具有较高的对映选择性。
• The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp³)–O Arylation
  作者：L. Reginald Mills、John J. Monteith、Gabriel dos Passos Gomes、Alán Aspuru-Guzik、Sophie A. L. Rousseaux

  DOI：10.1021/jacs.0c06904

  日期：2020.7.29

  understand and predict reactivity is highly important for the development of new reactions. In the context of Ni-catalyzed C(sp3)-O functionalization, we have developed a unique strategy employing activated cyclopropanols to aid the design and optimization of a redox-active leaving group for C(sp3)-O arylation. In this chemistry, the cyclopropane ring acts as a reporter of leaving-group reactivity, since the

  理解和预测反应性的能力对于新反应的发展非常重要。在 Ni 催化的 C(sp3)-O 官能化的背景下，我们开发了一种独特的策略，采用活化的环丙醇来帮助设计和优化用于 C(sp3)-O 芳基化的氧化还原活性离去基团。在该化学中，环丙烷环充当离去基团反应性的报告分子，因为在极性 (2e) 条件下获得开环产物，而在自由基 (1e) 条件下获得闭环产物。机理研究表明，最佳离去基团具有氧化还原活性，并且与 Ni(I)/Ni(III) 催化循环一致。优化的反应条件还用于合成许多芳基环丙烷，它们是有价值的药物基序。
• A Cobalt-Catalyzed Enantioconvergent Radical Negishi C(sp³)–C(sp²) Cross-Coupling with Chiral Multidentate <i>N</i>,<i>N</i>,<i>P</i>-Ligand
  作者：Zhuang Li、Xian-Yan Cheng、Ning-Yuan Yang、Ji-Jun Chen、Wen-Yue Tang、Jun-Qian Bian、Yong-Feng Cheng、Zhong-Liang Li、Qiang-Shuai Gu、Xin-Yuan Liu

  DOI：10.1021/acs.organomet.1c00190

  日期：2021.7.26

  cobalt-catalyzed enantioconvergent radical Negishi C(sp3)–C(sp2) cross-coupling of racemic benzyl chlorides with arylzinc reagents has been developed in good yield with moderate enantioselectivities. This strategy provides an expedient access toward a range of enantioenriched 1,1-diarylmethanes. Key to this discovery is the utilization of a chiral multidentate anionic N,N,P-ligand to strongly coordinate with the

  钴催化的对映聚合自由基 Negishi C(sp 3 )–C(sp 2 ) 的外消旋苄基氯与芳基锌试剂的交叉偶联已经以良好的收率和中等的对映选择性开发出来。该策略为获得一系列对映体富集的 1,1-二芳基甲烷提供了便利。这一发现的关键是利用手性多齿阴离子N , N , P配体与钴催化剂强配位并调节其手性环境，从而实现对高反应性前手性烷基自由基物种的对映控制。
• Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes
  作者：Qi Zhou、Harathi D. Srinivas、Srimoyee Dasgupta、Mary P. Watson

  DOI：10.1021/ja312087x

  日期：2013.3.6

  We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.