naphthalen-2-yl(phenyl)methyl pivalate | 1554400-65-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-2-yl(phenyl)methyl pivalate
• 英文别名: (2-naphthyl)(phenyl)methyl pivalate
• CAS: 1554400-65-5
• 化学式: C₂₂H₂₂O₂
• 分子量: 318.415
• InChiKey: CTGQGBUBVXMYMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  naphthalen-2-yl(phenyl)methyl pivalate 在 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 cesium fluoride 、 三对苯甲基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 2-甲基-2-丁醇 、 水 为溶剂， 反应 18.0h， 生成 2-(2-(4-methoxyphenyl)-1-phenylethyl)naphthalene
  参考文献：
  名称：

  二芳基甲醇衍生物与二硼基甲烷的钯催化交叉偶联反应

  摘要：

  已经开发了二芳基甲醇衍生物与二硼基甲烷的钯催化交叉偶联反应。该反应化学选择性地进行，以良好的产率递送相应的高苄基硼酸盐。

  DOI：

  10.1021/acs.joc.2c00715
• 作为产物：
  描述：

  2-萘甲醛 在 正丁基锂 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 27.0h， 生成 naphthalen-2-yl(phenyl)methyl pivalate
  参考文献：
  名称：

  Synthesis of Triarylmethanes by Palladium-Catalyzed C–H/C–O Coupling of Oxazoles and Diarylmethanol Derivatives

  摘要：

  A PdCl2(MeCN)2/PPhCy2 catalyst couples oxazoles with diarylmethyl carbonates or pivalates to form the corresponding triarylmethanes in good yields. The catalysis involves successive secondary benzylic sp(3) C-O and heteroaromatic sp(2) C-H cleavages and provides an effective access to heteroarene-containing triarylmethanes from nonhalogenated and nonmetalated starting materials, which is complementary to precedented cross-coupling technologies with organic halides and organometallic reagents.

  DOI：

  10.1021/jo5010636

文献信息

• Divergent Synthesis of Isonitriles and Nitriles by Palladium-Catalyzed Benzylic Substitution with TMSCN
  作者：Kento Asai、Koji Hirano、Masahiro Miura

  DOI：10.1021/acs.joc.0c01861

  日期：2020.10.2

  Ligand-controlled palladium-catalyzed divergent synthesis of isonitriles and nitriles from benzylic carbonates and TMSCN has been developed. The BINAP- or DPEphos-ligated palladium catalyst selectively provides the corresponding benzylic isonitriles, whereas their regioisomers, benzylic nitriles, are formed exclusively under phosphine ligand-free conditions. Mechanistic studies reveal that isonitrile

  已经开发了由碳酸苄基酯和TMSCN进行配体控制的钯催化的异腈和腈的发散合成。BINAP或DPEphos连接的钯催化剂选择性地提供相应的苄基异腈，而它们的区域异构体苄基腈仅在无膦配体的条件下形成。机理研究表明，在两种条件下，异腈都是主要产物，但在没有辅助膦配体的情况下，它会异构化为腈。
• Palladium-Catalyzed Asymmetric Benzylic Alkylation of Active Methylene Compounds with α-Naphthylbenzyl Carbonates and Pivalates
  作者：Sho Tabuchi、Koji Hirano、Masahiro Miura

  DOI：10.1002/anie.201602075

  日期：2016.6.6

  Pd/(R)‐H8‐BINAP‐catalyzed asymmetric benzylic alkylation of active methylene compounds has been developed. The reaction proceeds without the use of an external base, and the starting racemic diarylmethyl carbonates are converted into the optically active coupling products which contain the benzylic chiral stereocenter by a dynamic kinetic asymmetric transformation (DYKAT). Additionally, with suitable

  已开发出Pd /（R）-H 8 -BINAP催化的活性亚甲基化合物的不对称苄基烷基化反应。反应在不使用外部碱的情况下进行，并且起始外消旋碳酸二芳基甲基碳酸酯通过动态动力学不对称转化（DYKAT）被转化为包含苄基手性立体中心的旋光偶联产物。另外，对于合适的碳酸盐碱，相同的钯催化作用允许在相同的DYKAT工艺中采用相应的新戊酸酯。
• Asymmetric Synthesis of Diarylmethyl Sulfones by Palladium-Catalyzed Enantioselective Benzylic Substitution: A Remarkable Effect of Water
  作者：Atifah Najib、Koji Hirano、Masahiro Miura

  DOI：10.1002/chem.201800744

  日期：2018.5.2

  A Pd/(R)‐BINAP‐catalyzed enantioselective benzylic sulfonation of diarylmethyl carbonates with sodium sulfinates proceeds to deliver the corresponding chiral diarylmethyl sulfones in good yields with high enantioselectivity. The reaction occurs in a dynamic kinetic asymmetric transformation (DYKAT) manner and thus provides convergent access to optically active benzylic sulfones from racemic secondary

  Pd /（R）-BINAP催化的亚磺酸钠与碳酸二芳基甲基酯的对映选择性苄基磺化反应可以高收率和高对映选择性地提供相应的手性二芳基甲基砜。该反应以动态动力学不对称转化（DYKAT）方式发生，因此提供了从外消旋仲碳酸苄基酯到光学活性苄砜的会聚途径。另外，发现H 2 O的添加对于高对映选择性是至关重要的。
• Palladium‐Catalyzed Benzylic Silylation of Diarylmethyl Carbonates with Silylboranes under Base‐Free Conditions
  作者：Kento Asai、Koji Hirano、Masahiro Miura

  DOI：10.1002/ejoc.202101535

  日期：2022.5.6

  developed. By taking advantage of in-situ generated alkoxide ligand arising from the carbonate substrate, the reaction proceeds smoothly even under external base-free conditions. The resulting benzyl silane moiety can undergo the post functionalizations to deliver the more complex diarylmethane derivatives. Additionally, the related base-free allylic silylation reaction is also demonstrated.

  已开发出钯催化的二芳基甲基碳酸酯与甲硅烷基硼烷的苄基甲硅烷基化反应。通过利用碳酸盐底物原位生成的醇盐配体，即使在外部无碱条件下，反应也能顺利进行。所得苄基硅烷部分可以进行后官能化以提供更复杂的二芳基甲烷衍生物。此外，还展示了相关的无碱烯丙基甲硅烷基化反应。
• A Mild Ni/Cu-Catalyzed Silylation via C<i>–</i>O Cleavage
  作者：Cayetana Zarate、Ruben Martin

  DOI：10.1021/ja412107b

  日期：2014.2.12

  A Ni/Cu-catalyzed silylation of unactivated C-O electrophiles derived from phenols or benzyl alcohols is described. This transformation is characterized by its wide scope and mild conditions, providing a direct access to synthetically versatile silylated compounds. The protocol allows for the coupling of C(sp(2))-O and even C(sp(3))-O bonds with similar efficiency.