S-(naphthalen-2-yl) 2,2-dimethylpropanethioate | 155784-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S-(naphthalen-2-yl) 2,2-dimethylpropanethioate
• 英文别名: S-naphthalen-2-yl 2,2-dimethyl-thiopropanoate；S-naphthalen-2-yl 2,2-dimethylpropanethioate
• CAS: 155784-67-1
• 化学式: C₁₅H₁₆OS
• 分子量: 244.357
• InChiKey: KNGWOVUHMZOPGC-UHFFFAOYSA-N

物化性质

• 沸点：
  371.4±11.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-(naphthalen-2-yl) 2,2-dimethylpropanethioate 在 bis(1,5-cyclooctadiene)nickel (0) 、 二甲基乙基硅烷 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以18%的产率得到萘
  参考文献：
  名称：

  惰性碳-硫键的无配体镍催化还原裂解

  摘要：

  提出了在无配体条件下C（sp 2）–和C（sp 3）–SMe键的催化还原裂解。该方法的特点是适用范围广，化学选择性高，包括具有挑战性的底物组合，可设计正交和位点选择性方法。

  DOI：

  10.1021/ol2033306
• 作为产物：
  描述：

  三甲基乙酸酐 、 2-萘硫醇 在 molybdenium(VI) dioxodichloride 作用下， 以 二氯甲烷 为溶剂， 反应 144.5h， 以96%的产率得到S-(naphthalen-2-yl) 2,2-dimethylpropanethioate
  参考文献：
  名称：

  Nucleophilic Acyl Substitutions of Anhydrides with Protic Nucleophiles Catalyzed by Amphoteric, Oxomolybdenum Species

  摘要：

  [GRAPHICS]Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride -MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-alpha-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O-2-CBut)(2) between pivalic anhydride and MoO2Cl2 as the catalyst.

  DOI：

  10.1021/jo048363v

文献信息

• Nickel‐Mediated Trifluoromethylation of Phenol Derivatives by Aryl C−O Bond Activation
  作者：Wei‐Qiang Hu、Shen Pan、Xiu‐Hua Xu、David A. Vicic、Feng‐Ling Qing

  DOI：10.1002/anie.202004116

  日期：2020.9.7

  trifluoromethylation reactions. Tremendous efforts have focused on copper‐ and palladium‐mediated/catalyzed trifluoromethylation of aryl halides. In contrast, no general method exists for the conversion of widely available inert electrophiles, such as phenol derivatives, into the corresponding trifluoromethylated arenes. Reported herein is a practical nickel‐mediated trifluoromethylation of phenol derivatives with readily

  三氟甲基芳烃的药物重要性的提高刺激了更有效的三氟甲基化反应的发展。大量努力集中于铜和钯介导的/催化的芳基卤化物的三氟甲基化。相反，不存在将广泛使用的惰性亲电子试剂如苯酚衍生物转化为相应的三氟甲基化芳烃的通用方法。本文报道的是苯酚衍生物与容易获得的三甲基（三氟甲基）硅烷（TMSCF 3）进行的镍介导的三氟甲基化反应。该策略依赖于PMe 3促进的氧化加成和过渡金属化以及CCl 3CN诱导的还原消除。通过将三氟甲基直接掺入芳族和杂芳族体系（包括生物相关化合物）中，已证明了这种转化的广泛用途。
• Beyond Amide Bond Formation: TCFH as a Reagent for Esterification
  作者：Nathaniel R. Luis、Kasey K. Chung、Matthew R. Hickey、Ziqing Lin、Gregory L. Beutner、David A. Vosburg

  DOI：10.1021/acs.orglett.3c01611

  日期：2024.4.12

  In this Communication, an investigation of the combination of N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI) for the synthesis of esters and thioesters is described. This work revealed the unique challenges of the reactions of less nucleophilic alcohols and more reactive thiols with the N-acyl imidazolium intermediate and led to the identification of

  在本通讯中，描述了N , N , N ', N '-四甲基氯甲脒六氟磷酸盐 (TCFH) 和N-甲基咪唑 (NMI) 组合用于合成酯和硫酯的研究。这项工作揭示了亲核性较低的醇和反应性较高的硫醇与N-酰基咪唑鎓中间体反应的独特挑战，并确定了为一系列醇和硫醇提供高产率和选择性的一般有利条件。
• Catalytic Nucleophilic Acyl Substitution of Anhydrides by Amphoteric Vanadyl Triflate
  作者：Chien-Tien Chen、Jen-Huang Kuo、Chun-Hsin Li、N. B. Barhate、Sang-Wen Hon、Tai-Wei Li、Shi-Deh Chao、Chia-Cheng Liu、Ying-Chieh Li、I-Hsin Chang、Jin-Sheng Lin、Chin-Jing Liu、Y-Chen Chou

  DOI：10.1021/ol016684c

  日期：2001.11.1

  [GRAPHICS]Among four vanadyl species examined, vanadyl triflate was the most efficient catalyst to facilitate nucleophilic acyl substitution of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. By using mixed-anhydride technique, one can achieve oleate and peptide syntheses. In marked contrast to common metal triflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.
• Generation of Acyl Radicals From 2-Naphthyl Thioesters
  作者：John H. Penn、Fang Liu

  DOI：10.1021/jo00088a053

  日期：1994.5

  A series of S-2-naphthyl thioesters were synthesized from the corresponding carboxylic acids or acid chlorides. Irradiation of these thioesters in the presence of a hydrogen source (i.e., 1,4-cyclohexadiene) generated the corresponding aldehydes. In this fashion, primary, secondary, tertiary, and aryl carboxylic acids were converted to the aldehydes in high yields. Intramolecular radical cyclization reactions support the hypothesis that the reaction proceeds via the formation of acyl radicals. The formation of aldehydes was not perturbed by possible Norrish Type II reactions.
• Penn John H., Liu Fang, J. Org. Chem, 59 (1994) N 9, S 2608-2612
  作者：Penn John H., Liu Fang

  DOI：——

  日期：——