Toluene-4-sulfonic acid adamantan-1-yl ester | 16200-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid adamantan-1-yl ester
• 英文别名: 1-Adamantyl-p-toluolsulfonat；Adamantyl tosylate；1-adamantyl 4-methylbenzenesulfonate
• CAS: 16200-57-0
• 化学式: C₁₇H₂₂O₃S
• 分子量: 306.426
• InChiKey: NXWLBPXMYIJVPC-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C(Solv: methanol (67-56-1))
• 沸点：
  436.6±14.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid adamantan-1-yl ester 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 84.0h， 生成
  参考文献：
  名称：

  Solvolysis-decomposition ofN-1-adamantyl-N-p-tolylcarbamoyl chloride in hydroxylic solvents

  摘要：

  In hydroxylic solvents, N-1-adamantyl-N-p-tolylcarbamoyl chloride undergoes a facile rate-determing ionization with very little assistance from nucleophilic solvation (very low sensitivity to changes in solvent nucleophillcity). In the relatively nucleophilic aqueous ethanol or aqueous acetone, the cation formed reacts directly with the solvent. In fluoroalcohols, the low nucleophilicity of the solvent allows an effective competition from a pathway involving disproportionation to the 1-adamantyl cation and p-tolyl isocyanate, followed by reaction of the new cation either with solvent or with the chloride ion formed in the initial ionization, Grunwald-Winstein plots against Y-Cl values show for different binary solvent systems a marked dispersion, which can be considerably reduced by incorporation into the analyses of a term governed by the aromatic ring parameter. (I). (C) 1997 by John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199708)10:8<600::aid-poc928>3.0.co;2-q
• 作为产物：
  描述：

  4-甲苯磺酰氰 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 Toluene-4-sulfonic acid adamantan-1-yl ester
  参考文献：
  名称：

  O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide.

  摘要：

  Reaction of p-toluenesulfonyl cyanide or methanesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates 9 and 21 is suggested.

  DOI：

  10.1016/s0040-4020(01)96204-0

文献信息

• Solvent-free and selective tosylation of alcohols and phenols with <i>p</i>-toluenesulfonyl chloride by heteropolyacids as highly efficient catalysts
  作者：Razieh Fazaeli、Shahram Tangestaninejad、Hamid Aliyan

  DOI：10.1139/v06-066

  日期：2006.5.1

  Tosylation of some alcohols and phenols has been directly carried out with p-toluenesulfonyl chloride using heterodoxy acids (H3PW12O40, H3PMo12O40, AlPW12O40, and AlPMo12O40) as catalysts in the absence of solvent. We found that heteropoly acids AlPW12O40 and AlPMo12O40 were effective catalysts for the tosylation of alcohols and phenols. In the case of aliphatic alcohols, secondary alcohols undergo

  在没有溶剂的情况下，使用杂多氧基酸（H3PW12O40、H3PMo12O40、AlPW12O40 和 AlPMo12O40）作为催化剂，直接用对甲苯磺酰氯对某些醇和酚进行甲苯磺酰化。我们发现杂多酸 AlPW12O40 和 AlPMo12O40 是醇和酚甲苯磺酰化的有效催化剂。在脂肪醇的情况下，仲醇在伯羟基的存在下化学选择性地进行甲苯磺酰化。这种新方法始终具有收率高、反应时间短的优点。关键词：甲苯磺酰化，p-TsCl，Keggin型多金属氧酸盐，无溶剂反应。
• Classical carbonium ions. Part II. Synthesis, properties, and solvolysis of alkyl picrates and related compounds. A comparison of arenesulphonate and phenoxide leaving groups
  作者：M. L. Sinnott、M. C. Whiting

  DOI：10.1039/j29710000965

  日期：——

  Alkyl picrates can be prepared from picryl fluoride and a wide variety of primary, secondary, and bridgehead tertiary alcohols in the presence of tertiary amines. They can be cleaved, with aryl–oxygen fission, by aqueous ammonia, but solvolyse, with exclusive alkyl–oxygen fission, at rates comparable with those of corresponding toluenesulphonates, in ethanol and acetic acid. Chromophoric changes make

  可以在叔胺存在下，由氟化苦味酚和各种伯，仲和桥头叔叔醇制备苦味烷基酯。可以用氨水将芳基-氧裂变裂解，而在仅用烷基-氧裂变的情况下，溶剂分解法可以在乙醇和乙酸中以与相应的甲苯磺酸盐相当的速率裂解。发色变化使这些反应易于跟踪。苦味离开小组可能有综合性申请。在溶剂分解中，速率和产物研究表明，相邻基团或溶剂的亲核参与比在芳烃磺酸酯的相应反应中更重要。
• 一种碳糖苷类钠葡萄糖转运蛋白体2抑制剂
  申请人：江苏天士力帝益药业有限公司

  公开号：CN108285439B

  公开（公告）日：2023-05-02

  本发明涉及一种碳糖苷类钠葡萄糖转运蛋白体2抑制剂，其制备方法和用途，本发明的碳糖苷类钠葡萄糖转运蛋白体2抑制剂，具有通式(Ⅰ)的结构
• Polar Effects. Part 15. Twin γ-substituent effects in the formation of adamantyl-1-cations
  作者：Cyril A. Grob、Martin Gründel、Pawel Sawlewicz

  DOI：10.1002/hlca.19880710615

  日期：1988.9.28

  adamant-1-yl ( = tricyclo[3.3.1.13,7]dec-1-yl) p-toluenesulfonates and bromides 2 identically substituted at C(3) and C(5) (twin substitution) have been determined and compared with the rates of the corresponding 3-monosubstituted compounds 1. As expected, the rate factors for twin substitution are much larger, but less than the square of the rate factors for single substitution. Also the rates factors

  几个在C（3）和C（5）相同取代的金刚烷基-1-基（=三环[3.3.1.1 3,7 ]癸-1-基）对甲苯磺酸盐和溴化物2的溶剂分解速率已经达到确定并与相应的3-单取代化合物的比率进行比较。如预期的那样，双取代的比率因子要大得多，但小于单取代的比率因子的平方。同样，2中每个替代品的费率因子比1中一个替代品的费率因子小得多。该衰减归因于电子排斥，该电子排斥限制了电子密度向阳离子中心的收敛。在另一方面，对于双取代的电感（ρ 1 = -2.55）是大约两倍高为单取代（ρ 1 = -1.26）。
• REACTION OF<i>exo</i>-2-NORBORNYL AND 1-ADAMANTYL<i>p</i>-TOLUENESULFONATES WITH SODIUM PHENOXIDE IN TETRAHYDROFURAN. IONIZATION OF THE SUBSTRATES UNDER “APPARENTLY-S_N2” CONDITIONS
  作者：Ken’ichi Takeuchi、Yukari Kato、Takamasa Moriyama、Kunio Okamoto

  DOI：10.1246/cl.1981.935

  日期：1981.7.5

  exo-2-Norbornyl and 1-adamantyl tosylates react with sodium phenoxide in tetrahydrofuran via ionization, most probably through a cyclic transition state. The results call for attention in interpreting substitution reactions under “apparently-SN2” conditions.

  exo-2-Norbornyl 和 1-adamantyl tosylates 与苯酚钠在四氢呋喃中通过电离反应，最有可能通过循环过渡态。在解释“明显-SN2”条件下的取代反应时，该结果需要引起注意。