phenyl 1-naphthylacetate | 51537-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: phenyl 1-naphthylacetate
• 英文别名: 1-naphthaleneacetic acid phenyl ester；phenyl 2-(naphthalen-1-yl)acetate；Phenyl 2-naphthalen-1-ylacetate
• CAS: 51537-84-9
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: PKVFJKTWORPYMS-UHFFFAOYSA-N

物化性质

• 沸点：
  440.9±24.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyl 1-naphthylacetate 以40%的产率得到
  参考文献：
  名称：

  Yamamoto Jiro, Tamura Hironori, Takahara Kouichi, Yamana Hideaki, Maeta K+, Nippon kagaku kaishi (J. Chem. Soc. Jap), (1994) N 8, S 707-712

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-2-(naphthalen-1-yl)ethan-1-one 以27%的产率得到
  参考文献：
  名称：

  Yamamoto Jiro, Tamura Hironori, Takahara Kouichi, Yamana Hideaki, Maeta K+, Nippon kagaku kaishi (J. Chem. Soc. Jap), (1994) N 8, S 707-712

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Decarboxylative Carbonylative Transformation of Benzyl Aryl Carbonates: Direct Synthesis of Aryl 2-Arylacetates
  作者：Jian-Xing Xu、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.8b02631

  日期：2018.9.21

  A procedure on palladium-catalyzed decarboxylative alkoxycarbonylation of carbonates for the synthesis of aryl 2-arylacetates has been developed. A broad range of aryl 2-arylacetates were obtained in good yields under mild conditions under a carbon monoxide atmosphere. Interestingly, other alcohols can be added as nucleophiles as well, and the corresponding esters were also obtained in good yields

  已经开发了钯催化碳酸酯的脱羧烷氧基羰基化反应以合成芳基2-芳基乙酸酯的方法。在温和的条件下，在一氧化碳气氛下，以良好的收率获得了广泛的2-芳基乙酸芳基酯。有趣的是，也可以添加其他醇作为亲核试剂，并且也以高收率获得了相应的酯。
• Catalytic α-Arylation of Ketones with Heteroaromatic Esters
  作者：Junichiro Yamaguchi、Ryota Isshiki、Ryosuke Takise、Kenichiro Itami、Kei Muto

  DOI：10.1055/s-0036-1589120

  日期：2017.12

  Heteroaromatic esters were found to be applicable as an arylating agent for the Pd-catalyzed α-arylation of ketones in a decarbonylative fashion. The use of our in-house ligand, dcypt, enabled this unique bond formation. Considering the ubiquity and low cost of ­aromatic esters, the present work will allow for rapid access to valuable α-aryl carbonyl compounds.

  发现杂芳族酯可用作芳基化剂，用于 Pd 催化的酮以脱羰方式进行 α-芳基化。使用我们的内部配体 dcypt 实现了这种独特的键形成。考虑到芳香酯的普遍性和低成本，目前的工作将允许快速获得有价值的 α-芳基羰基化合物。
• Indium-Catalyzed Reductive Sulfid­ation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides
  作者：Takahiro Miyazaki、Shinsei Kasai、Yohei Ogiwara、Norio Sakai

  DOI：10.1002/ejoc.201501559

  日期：2016.2

  unsymmetrical sulfides from esters and thiols in the presence of InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 as the reductant was developed. This protocol was applied to not only benzoic acid esters that have a methoxy, methyl, chloro, bromo, iodo, or trifluoromethyl group on the aromatic ring but also aliphatic acid esters with either aromatic or aliphatic thiols. A reaction mechanism

  在 InI3 和 1,1,3,3-四甲基二硅氧烷 (TMDS) 或 PhSiH3 作为还原剂的存在下，开发了一种新的由酯和硫醇还原制备不对称硫化物的方法。该方案不仅适用于在芳环上具有甲氧基、甲基、氯、溴、碘或三氟甲基的苯甲酸酯，还适用于具有芳香或脂肪硫醇的脂肪酸酯。通过使用哈米特图结果和几个控制实验提出了反应机制。
• New methods and reagents in organic synthesis. 17. Trimethylsilyldiazomethane(TMSCHN2) as a stable and safe substitute for hazardous diazomethane. Its application to the arndt-eistert synthesis.
  作者：TOYOHIKO AOYAMA、TAKAYUKI SHIOIRI

  DOI：10.1248/cpb.29.3249

  日期：——

  Although diazomethane is used in the Arndt-Eistert synthesis, it is both highly toxic and also explosive, and hence should be very carefully handled. In place of this hazardous diazomethane, stable and safe trimethylsilyldiazomethane (TMSCHN2) was found to be very useful for the Arndt-Eistert synthesis. TMSCHN2 was easily acylated with a carboxylic acid chloride in tetrahydrofuran-acetonitrile, and thermal treatment of the acylated product in benzyl alcohol and 2, 4, 6-trimethylpyridine smoothly gave the benzyl ester of a homologated acid. Nucleophiles other than benzyl alcohol could also be used. TMSCHN2 may also be able to replace diazomethane in other areas of chemistry.

  尽管偶氮甲烷在阿恩特-艾斯特合成中使用，但它具有高毒性和爆炸性，因此应该非常小心地处理。为了替代这种危险的偶氮甲烷，稳定且安全的三甲基硅烷偶氮甲烷（TMSCHN₂）被发现对于阿恩特-艾斯特合成非常有用。TMSCHN₂可以在四氢呋喃-乙腈中与卤代羧酸酰氯轻松进行酰化，酰化产物在苄醇和2,4,6-三甲基吡啶中的热处理顺利得到了一种同 homologated acid 的苄酯。除了苄醇之外，其他亲核试剂也可以使用。TMSCHN₂可能还能够替代偶氮甲烷在其他化学领域的应用。
• Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates
  作者：Lin Guo、Magnus Rueping

  DOI：10.1002/chem.201604504

  日期：2016.11.14

  A new and efficient nickel‐catalyzed decarbonylative borylation reaction of carboxylic acid esters with bis(pinacolato)‐diboron has been developed. This transformation allows access to structurally diverse aryl as well as alkenyl and alkyl boronate esters with high reactivity, broad substrate scope, and excellent functional‐group tolerance. Further experiments show that this protocol can be carried

  开发了一种新的，高效的镍催化的羧酸酯与双（频哪醇）二硼烷的脱羰基硼酸酯化反应。通过这种转变，可以得到具有高反应活性，广泛的底物范围和出色的官能团耐受性的结构多样的芳基以及烯基和烷基硼酸酯。进一步的实验表明，该协议可以以克为单位进行，并应用于正交合成策略。