5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2,3-diamine | 81864-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2,3-diamine
• 英文别名: 2,3-diamino-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene；5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2,3-naphthalenediamine；5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2,3-diamine
• CAS: 81864-05-3
• 化学式: C₁₄H₂₂N₂
• 分子量: 218.342
• InChiKey: PZMRGRMXDSKLIG-UHFFFAOYSA-N

物化性质

• 沸点：
  355.9±42.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2,3-diamine 在 sodium hydride 作用下， 以 xylene 为溶剂， 反应 3.0h， 生成 methyl 4-(1H-2,3,7,8,9,10-hexahydro-1,7,7,10,10-pentamethyl-2-oxonaphtho<2,3-b><1,4>diazepin-4-yl)benzoate
  参考文献：
  名称：

  Retinobenzoic Acids. 6. Retinoid Antagonists with a Heterocyclic Ring

  摘要：

  Several candidate retinoid antagonists were designed on the basis of the ligand superfamily concept and synthesized. Retinoidal activities of these benzimidazole and benzodiazepine derivatives were examined by assay of differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. The parent benzimidazole derivative, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnapth[2,3-d]imidazol-2-yl)benzoic acid (7a), and related compounds with a small alkyl group instead of the hydrogen on the nitrogen (N-1) atom of the imidazole ring exhibited retinoidal activity, and the potency strongly depended on the bulkiness of the substituent. The compounds having a phenyl or benzyl group on the nitrogen lacked differentiation-inducing activity on HL-60 cells and acted as antagonists to the potent retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)carbamoyl]benzoic acid (Am80). Among the compounds possessing a seven-membered heterocyclic ring as a linking group, 4-(5H-7,8,9,10-tetrahydro-5,7,7,10,10-pentamethylbenzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid (16) also exhibited the antagonistic activity. The binding abilities of these compounds to retinoic acid receptors ct and P were consistent with their potency for the inhibition of HL-60 cell differentiation induced by the retinoid Am80.

  DOI：

  10.1021/jm00036a017
• 作为产物：
  描述：

  5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-nitro-2-naphthylamine 在 盐酸 、 铁粉 作用下， 反应 0.5h， 以76%的产率得到5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2,3-diamine
  参考文献：
  名称：

  Retinobenzoic Acids. 6. Retinoid Antagonists with a Heterocyclic Ring

  摘要：

  Several candidate retinoid antagonists were designed on the basis of the ligand superfamily concept and synthesized. Retinoidal activities of these benzimidazole and benzodiazepine derivatives were examined by assay of differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. The parent benzimidazole derivative, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnapth[2,3-d]imidazol-2-yl)benzoic acid (7a), and related compounds with a small alkyl group instead of the hydrogen on the nitrogen (N-1) atom of the imidazole ring exhibited retinoidal activity, and the potency strongly depended on the bulkiness of the substituent. The compounds having a phenyl or benzyl group on the nitrogen lacked differentiation-inducing activity on HL-60 cells and acted as antagonists to the potent retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)carbamoyl]benzoic acid (Am80). Among the compounds possessing a seven-membered heterocyclic ring as a linking group, 4-(5H-7,8,9,10-tetrahydro-5,7,7,10,10-pentamethylbenzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid (16) also exhibited the antagonistic activity. The binding abilities of these compounds to retinoic acid receptors ct and P were consistent with their potency for the inhibition of HL-60 cell differentiation induced by the retinoid Am80.

  DOI：

  10.1021/jm00036a017

文献信息

• Imidazole derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04435406A1

  公开（公告）日：1984-03-06

  Tricyclic imidazole derivatives of the formula ##STR1## wherein R.sup.1 is 2-pyridyl optionally substituted by lower alkyl or lower alkoxy, n is the integer 0 or 1, R.sup.2 is hydrogen or lower alkyl, R.sup.3 and R.sup.4, independently, are hydrogen or lower alkyl, A is a group of the formula ##STR2## m is the integer 2 or 3, R.sup.5, R.sup.6, R.sup.7 and R.sup.8, independently, are hydrogen or lower alkyl, and R.sup.9 is hydrogen and R.sup.10 is hydrogen or lower alkyl or R.sup.9 and R.sup.10 taken together are oxo, provided that at least one of R.sup.3 and R.sup.4 is lower alkyl when A is a group of the formula --CH.dbd.CH--CH.dbd.CH-- or --(CH.sub.2).sub.4 --, and their pharmaceutically acceptable acid addition salts. The compounds of formula I inhibit gastric acid secretion and prevent the formation of gastric ulcers.

  Tricyclic imidazole derivatives of the formula ##STR1## wherein R.sup.1 is 2-pyridyl optionally substituted by lower alkyl or lower alkoxy, n is the integer 0 or 1, R.sup.2 is hydrogen or lower alkyl, R.sup.3 and R.sup.4, independently, are hydrogen or lower alkyl, A is a group of the formula ##STR2## m is the integer 2 or 3, R.sup.5, R.sup.6, R.sup.7 and R.sup.8, independently, are hydrogen or lower alkyl, and R.sup.9 is hydrogen and R.sup.10 is hydrogen or lower alkyl or R.sup.9 and R.sup.10 taken together are oxo, provided that at least one of R.sup.3 and R.sup.4 is lower alkyl when A is a group of the formula --CH.dbd.CH--CH.dbd.CH-- or --(CH.sub.2).sub.4 --, and their pharmaceutically acceptable acid addition salts. The compounds of formula I inhibit gastric acid secretion and prevent the formation of gastric ulcers.
• C–H Amination of Arenes with Hydroxylamine
  作者：Yi Yang See、Melanie S. Sanford

  DOI：10.1021/acs.orglett.0c00598

  日期：2020.4.17

  This Letter describes the development of a TiIII-mediated reaction for the C–H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (<30 min), compatibility with ambient moisture and air, scalability

  这封信描述了钛III介导的芳烃与羟胺的CH胺化反应的发展。该反应适用于多种富电子（杂）芳烃底物，包括一系列天然产物和药物。它具有温和的条件（室温），快速的反应速率（<30分钟），与环境湿度和空气的相容性，可扩展性以及使用廉价的商业试剂的优势。
• Polycyclic heterocyclic compounds, a process for their preparation and
  申请人：Centre International de Recherches Dermatologiques (CIRD)

  公开号：US04874747A1

  公开（公告）日：1989-10-17

  A polycyclic heterocyclic compound has the formula ##STR1## wherein n is 1 or 2, R.sub.1 l represents (i) lower alkyl, (ii) --CH.sub.2 OH or (iii) ##STR2## R.sub.2 represents (a) hydrogen, (b) ##STR3## or (c)--OR.sub.3, R.sub.3 represents hydrogen, C.sub.1 -C.sub.20 alkyl mono or polyhydroxyalkyl, aryl or aralkyl optionally substituted, the residue of a sugar or ##STR4## wherein p is 1, 2, or 3, and r' and r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl optionally substituted, amino acid residue, aminated sugar residue, or together form a heterocycle, X represents oxygen, sulfur, SO, SO.sub.2 or --NR.sub.4, Y represents CR.sub.4 or a nitrogen atom and R.sub.4 represents hydrogen or lower alkyl. This polycyclic heterocyclic compound can be used in human and veterinary medicine and especially in the topical or systemic treatment of determatologic diseases.

  一种多环杂环化合物具有以下结构式：其中n为1或2，R.sub.1代表(i) 较低的烷基，(ii) --CH.sub.2 OH或(iii) R.sub.2代表(a) 氢，(b) 或(c)--OR.sub.3，R.sub.3代表氢，C.sub.1 -C.sub.20烷基单或多羟基烷基，芳基或芳基烷基，可选择性地取代，糖的残基或其中p为1，2或3的残基，r'和r"代表氢，较低的烷基，单或多羟基烷基，可选择性地取代的芳基，氨基酸残基，氨基化糖残基，或者共同形成一个杂环，X代表氧，硫，SO，SO.sub.2或--NR.sub.4，Y代表CR.sub.4或氮原子，R.sub.4代表氢或较低的烷基。这种多环杂环化合物可用于人类和兽医学，尤其是在治疗皮肤病方面的局部或全身治疗中。
• Absolute Helical Arrangement of Sulfonamide in the Crystal
  作者：Isao Azumaya、Takako Kato、Iwao Okamoto、Ryu Yamasaki、Aya Tanatani、Kentaro Yamaguchi、Hiroyuki Kagechika、Hiroaki Takayanagi

  DOI：10.1021/ol035509o

  日期：2003.10.1

  configurations of the chiral crystals of 2 were determined by X-ray crystal structure analysis using the Flack parameter method. The solid-state CD spectra of the chiral crystals in KBr were mirror images. The equilibrium between the two enantiomers in solution is fast during crystallization at ambient temperature, and the energy barrier (DeltaG()) is estimated to be 11.7 +/- 0.3 kcal/mol (233 K).

  [反应：请参见文本]没有固定不对称元素的1,2-双（N-苯磺酰基-N-甲基氨基）苯（2）从乙酸乙酯中结晶为属于空间群P4（1）2（的手性晶体） 1）2（第92号）或P4（3）2（1）2（第96号）。通过CH-pi相互作用沿c轴构建的分子阵列在每个单个晶体中形成对映体螺旋超结构。通过使用Flack参数法的X射线晶体结构分析来确定2的手性晶体的绝对构型。KBr中手性晶体的固态CD光谱为镜像。溶液中两种对映体之间的平衡在环境温度下的结晶过程中很快，并且能垒（DeltaG（））估计为11.7 +/- 0.3 kcal / mol（233 K）。
• Pyridyl methyl thio or sulfinyl indeno(5,6-d)imidazoles
  申请人：Hoffmann-La Roche Inc.

  公开号：US04554280A1

  公开（公告）日：1985-11-19

  Tricyclic imidazole derivatives of the formula ##STR1## wherein R.sup.1 is 2-pyridyl optionally substituted by lower alkyl or lower alkoxy, n is the integer 0 or 1, R.sup.2 is hydrogen or lower alkyl, R.sup.3 and R.sup.4, independently, are hydrogen or lower alkyl, A is a group of the formula ##STR2## m is the integer 2 or 3, R.sup.5, R.sup.6, R.sup.7 and R.sup.8, independently, are hydrogen or lower alkyl, and R.sup.9 is hydrogen and R.sup.10 is hydrogen or lower alkyl or R.sup.9 and R.sup.10 taken together are oxo, provided that at least one of R.sup.3 and R.sup.4 is lower alkyl when A is a group of the formula --CH.dbd.CH--CH.dbd.CH-- or --(CH.sub.2).sub.4 --, and their pharmaceutically acceptable acid addition salts. The compounds of formula I inhibit gastric acid secretion and prevent the formation of gastric ulcers.

  公式为 ##STR1## 的三环咪唑衍生物，其中R.sup.1是2-吡啶基，可选择地被低烷基或低烷氧基取代，n是整数0或1，R.sup.2是氢或低烷基，R.sup.3和R.sup.4独立地是氢或低烷基，A是公式 ##STR2## 的基团，m是整数2或3，R.sup.5，R.sup.6，R.sup.7和R.sup.8独立地是氢或低烷基，R.sup.9是氢，R.sup.10是氢或低烷基或R.sup.9和R.sup.10一起是氧代，但当A是公式--CH.dbd.CH--CH.dbd.CH--或--（CH.sub.2）.sub.4--的基团时，至少R.sup.3和R.sup.4中的一个是低烷基，它们的药学上可接受的酸盐。公式I的化合物抑制胃酸分泌并预防胃溃疡的形成。