2-butyl-1-naphthalenecarboxylic acid | 108122-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-butyl-1-naphthalenecarboxylic acid
• 英文别名: 2-butyl-[1]naphthoic acid；2-Butyl-[1]naphthoesaeure；2-n-Butyl-1-naphthoesaeure；2-Butyl-1-naphthoic acid；2-butylnaphthalene-1-carboxylic acid
• CAS: 108122-91-4
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: SAZAQXCDLPBCLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-Butyl-(1-naphthyl)-sulfon 以 乙醚 为溶剂， 生成 2-butyl-1-naphthalenecarboxylic acid
  参考文献：
  名称：

  芳基磺酰基化合物与过量的有机锂试剂-IV的反应：正丁基锂对叔丁基-1-萘砜的作用。叔丁基磺酰基的取代机理

  摘要：

  -n-BuLi与叔丁基-1-萘砜（I）在回流的乙醚中反应，然后进行水解碳化，得到2-正丁基萘甲酸和反式1,2-二氢-1-叔丁基磺酰基-2-正丁基萘。最可能的机理涉及首先将1,2,3 BuLi加到砜（I）中，然后在随后的步骤中消除叔丁基亚磺酸。MeLi在环的C-2处使砜（I）金属化。

  DOI：

  10.1016/s0040-4020(01)90713-6

文献信息

• METHOD FOR PREPARING CHEMICAL COMPOUNDS OF INTEREST BY NUCLEOPHILIC AROMATIC SUBSTITUTION OF AROMATIC CARBOXYLIC ACID DERIVATIVES SUPPORTING AT LEAST ONE ELECTRO-ATTRACTIVE GROUP
  申请人：Mortier Jacques

  公开号：US20120316337A1

  公开（公告）日：2012-12-13

  Method for preparing carboxylic acid derivatives by aromatic nucleophilic substitution, in which a carboxylic acid derivative having a single carboxyl functional group, or one of the salts thereof, the carboxylic acid derivative having, in the ortho position of the carboxyl functional group, a leaving group, which is preferably an atom of fluorine or of chlorine or an alkoxy group, chiral or not, preferably a methoxy group, the carboxylic acid derivative not being substituted by an electro attractive group other than the leaving group if any; is reacted with a reactant MNu, where M is a metal and Nu is a nucleophile, chiral or not, the aromatic nucleophilic substitution reaction being carried out without a catalyst and without a step of protecting/deprotecting the acid functional group of the starting compound.

  通过芳香亲核取代法制备羧酸衍生物的方法，其中羧酸衍生物具有单个羧基官能团，或其盐之一，该羧酸衍生物在羧基官能团的邻位具有一个离去基团，该离去基团优选为氟原子或氯原子或烷氧基，手性或非手性，优选为甲氧基，如果有的话，该羧酸衍生物未被电子亲合基团取代；与反应物MNu发生反应，其中M为金属，Nu为亲核试剂，手性或非手性，芳香亲核取代反应在无催化剂和无保护/去保护起始化合物的酸官能团的步骤的情况下进行。
• Synthesis of 1,2-Disubstituted Naphthalenes and Tetrahydronaphthalenes from Dihydronaphthalenes Obtained by Conjugate Addition of Organolithium Reagents to 2,6-Bis(tert-butyl)-4-methoxyphenyl Naphthalenecarboxylates.
  作者：Mitsuru SHINDO、Kenji KOGA、Kiyoshi TOMIOKA

  DOI：10.1248/cpb.47.1318

  日期：——

  A method of the conversion of 2, 6-bis(tert-butyl)-4-methoxyphenyl dihydronaphthalenecarboxylates into substituted naphthalenes and tetrahydronaphthalenes was developed. Aromatization of substituted dihydronaphthalenecarboxylates with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone and subsequent treatment with ceric ammonium nitrate (CAN) gave the corresponding substituted naphthalenecarboxylic acid. Alternatively, hydrogenolysis and subsequent treatment with CAN provided a way to tetrahydronaphthalenemethanols in good yields.

  开发了一种将2, 6-双(叔丁基)-4-甲氧基苯基二氢萘甲酸酯转化为取代萘和四氢萘的方法。用2, 3-二氯-5, 6-二氰基-1, 4-苯醌对取代的二氢萘甲酸酯进行芳构化，然后用硝酸高铈铵（CAN）处理，得到相应的取代萘甲酸酯。或者，氢解和随后的 CAN 处理提供了一种以良好产率生产四氢萘甲醇的方法。
• Huisgen; Zirngibl, Chemische Berichte, 1958, vol. 91, p. 1438,1451
  作者：Huisgen、Zirngibl

  DOI：——

  日期：——
• Conjugate addition reaction of organolithiums to naphthalenecarboxylates
  作者：Kiyoshi Tomioka、Mitsuru Shindo、Kenji Koga

  DOI：10.1016/s0040-4039(00)88868-1

  日期：1990.1
• Ali, Syed Masarrat; Tanimoto, Shigeo, Journal of the Chemical Society. Perkin transactions I, 1989, p. 915 - 918
  作者：Ali, Syed Masarrat、Tanimoto, Shigeo

  DOI：——

  日期：——