1,4-dihydro-7-methoxy-N-(1',1'-dimethylethyl)-N-methylnaphthalene-1-sulfonamide | 121429-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-dihydro-7-methoxy-N-(1',1'-dimethylethyl)-N-methylnaphthalene-1-sulfonamide
• 英文别名: N-tert-butyl-7-methoxy-N-methyl-1,4-dihydronaphthalene-1-sulfonamide
• CAS: 121429-73-0
• 化学式: C₁₆H₂₃NO₃S
• 分子量: 309.43
• InChiKey: PMEUPDBAJOJTDM-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  426.6±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-7-methoxy-N-(1',1'-dimethylethyl)-N-methylnaphthalene-1-sulfonamide 在 正丁基锂 作用下， 反应 3.33h， 生成 7-Methoxy-naphthoesaeure-(1)-methylester
  参考文献：
  名称：

  Metal-ammonia reduction and reductive alkylation of N-alkylnaphthalenesulfonamides. A new route to substituted naphthalenes

  摘要：

  Conditions have been found for 1,4-reduction of aromatic sulfonamides (conveniently monitored by electrical conductivity), using metals in THF/liquid ammonia on the pre-formed N-lithium salts (BuLi), without concomitant C-S reductive cleavage. The resulting 1,4-dihydro compounds could be alkylated, either in situ (in the case of simple unfunctionalized halides only) or, following isolation, after further N-alkylation and then forming the monoanion, or after forming the dianion of the N-monoalkylated dihydrosulfonamide, generally using as base n-butyllithium (a simple titration procedure). In the former case functionalized electrophiles (bromo esters, chloroformates) could be utilized. The ratio of alpha- to gamma-alkylation was dependent on the method of alkylation, the reaction medium, the nature of the N-alkyl group(s), and whether a monoanion or a dianion served as substrate. Gamma-Alkylation products could in some cases be further alpha-substituted. The alpha-substituted products aromatized, with loss of SO2 and amine, by heating, whereas gamma-substitution products required hydrolysis by aqueous alkali; this greatly facilitated separation where mixtures were formed. Thus, this dihydrosulfonamide route constitutes a novel and nucleophilic route to 1-substituted, 2-substituted, and, notably, 1,3-disubstituted naphthalenes.

  DOI：

  10.1021/jo00035a018
• 作为产物：
  描述：

  1,4-dihydro-7-methoxy-N-(1',1'-dimethylethyl)naphthalene-1-sulfonamide 、 碘甲烷 在 正丁基锂 作用下， 生成 1,4-dihydro-7-methoxy-N-(1',1'-dimethylethyl)-N-methylnaphthalene-1-sulfonamide
  参考文献：
  名称：

  Metal-ammonia reduction and reductive alkylation of N-alkylnaphthalenesulfonamides. A new route to substituted naphthalenes

  摘要：

  Conditions have been found for 1,4-reduction of aromatic sulfonamides (conveniently monitored by electrical conductivity), using metals in THF/liquid ammonia on the pre-formed N-lithium salts (BuLi), without concomitant C-S reductive cleavage. The resulting 1,4-dihydro compounds could be alkylated, either in situ (in the case of simple unfunctionalized halides only) or, following isolation, after further N-alkylation and then forming the monoanion, or after forming the dianion of the N-monoalkylated dihydrosulfonamide, generally using as base n-butyllithium (a simple titration procedure). In the former case functionalized electrophiles (bromo esters, chloroformates) could be utilized. The ratio of alpha- to gamma-alkylation was dependent on the method of alkylation, the reaction medium, the nature of the N-alkyl group(s), and whether a monoanion or a dianion served as substrate. Gamma-Alkylation products could in some cases be further alpha-substituted. The alpha-substituted products aromatized, with loss of SO2 and amine, by heating, whereas gamma-substitution products required hydrolysis by aqueous alkali; this greatly facilitated separation where mixtures were formed. Thus, this dihydrosulfonamide route constitutes a novel and nucleophilic route to 1-substituted, 2-substituted, and, notably, 1,3-disubstituted naphthalenes.

  DOI：

  10.1021/jo00035a018

文献信息

• Metal-ammonia reduction and reductive alkylation of naphthalene sulphonamides. A new route to substituted naphthalenes.
  作者：L. Gottlieb、H.J.E. Loewenthal

  DOI：10.1016/s0040-4039(00)80526-2

  日期：1988.1

  Conditions have been found for the successful Birch reduction and reductive alkylation of N-alkyl arylsulphonamides, specifically in the naphthalene series. The derived C-alkylation products smoothly fragment on heating with re-aromatisation, affording a new specific route to 1-substituted naphthalenes starting from the 1-sulphonamides, and to both 2-mono-substituted and 2,4- (or 1,3-) disubstituted

  已经发现成功地使N-烷基芳基磺酰胺的Birch还原和还原性烷基化的条件，特别是在萘系列中。衍生的C-烷基化产物在加热后随着重新芳构化而平滑地断裂，从而提供了一条新的特定路线，从1-磺酰胺类化合物到1-取代的萘，再到2-单取代和2,4-（或1,3） -）来自相应的2-磺酰胺的二取代的萘。
• γ-versusα-Substitution in dihydronaphthalene sulphonamides. A novel approach to (±)-Naproxen
  作者：H. J. E. Loewenthal

  DOI：10.1039/c39900000768

  日期：——

  Alkylation of N-alkyl dihydronaphthalene-1-sulphonamides, derived by reduction with Li/liq. NH3, can be directed in certain cases to the naphthalene 3-position, depending mainly on the steric bulk of the N-alkyl group(s).

  通过用Li / liq还原得到的N-烷基二氢萘-1-磺酰胺的烷基化。在某些情况下，NH 3可以直接指向萘的3-位，这主要取决于一个或多个N-烷基的空间体积。
• GOTTLIEB, L.;LOEWENTHAL, H. J. E., TETRAHEDRON LETT., 29,(1988) N 35, C. 4473-4476
  作者：GOTTLIEB, L.、LOEWENTHAL, H. J. E.

  DOI：——

  日期：——