2,3,8,9-tetrahydronaphtho[2,3-b][1,4]dioxin-6(7H)-one | 15128-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2,3,8,9-tetrahydronaphtho[2,3-b][1,4]dioxin-6(7H)-one
• 英文别名: 6-oxo-2,3,6,7,8,9-hexahydrobenzo[g][1,4]benzodioxine；2,3,8,9-tetrahydro-7H-naphtho[2,3-b][1,4]dioxin-6-one；3,7,8,9-tetrahydro-2H-benzo[g][1,4]benzodioxin-6-one
• CAS: 15128-62-8
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: HROJNZXITRNBCB-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C(Solv: ethanol (64-17-5))
• 沸点：
  376.3±42.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,8,9-tetrahydronaphtho[2,3-b][1,4]dioxin-6(7H)-one 在 镍 氢气 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-[2-(2,3,6,7,8,9-hexahydrobenzo[g][1,4]benzodioxin-6-yl)ethyl]acetamide
  参考文献：
  名称：

  Synthesis and biological activity of conformationally restricted tricyclic analogs of the hormone melatonin

  摘要：

  A serie of rotationally restricted tricyclic naphthalenic and tetrahydronaphthalenic analogs of the hormone melatonin has been synthesized, the C-7 oxygen being incorporated in a pyran, furan or dioxan heterocyclic ring. The receptor binding profile of these compounds is a function of the directionality of the lone pairs electrons of this C-7 oxygen. In these two studied analogous series the agonist activity seems to be correlated with the existence of a naphthalene nucleus. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00175-8
• 作为产物：
  描述：

  在 三氟化硼乙醚 四氢呋喃 、 mercury(II) oxide 作用下， 以55%的产率得到2,3,8,9-tetrahydronaphtho[2,3-b][1,4]dioxin-6(7H)-one
  参考文献：
  名称：

  1,3-benzodithiolium ion mediated annulations

  摘要：

  DOI：

  10.1016/s0040-4039(00)88063-6

文献信息

• An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and <i>β</i> -Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane
  作者：Perumal Saravanan、Pazhamalai Anbarasan

  DOI：10.1002/adsc.201800366

  日期：2018.8.6

  efficient and general trifluoromethylthiolation of silylenol ethers and β‐naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α‐trifluoromethylthiolated carbonyl compounds and β‐naphthols in good yields. Important features of this method

  利用二乙基氨基三氟化硫（DAST）和（三氟甲基）三甲基硅烷（CF 3 TMS）的组合作为合成三α-三氟甲硫基羰基化合物的亲电三氟甲硫基化合物，已经完成了甲硅烷基醚和β-萘酚的高效且通用的三氟甲硫基化反应。β萘酚的收率很高。该方法的重要特征包括宽泛的官能团耐受性和使用现成的DAST / CF 3 TMS。通过α-三氟甲基硫醇化（+）-4-胆甾烯-3-酮和萘醌的合成证明了该方法的潜力。
• Propanolaminomethyltetralines, their preparation and pharmaceutical composition comprising same
  申请人：Barzaghi Laura

  公开号：US20050054641A1

  公开（公告）日：2005-03-10

  The invention concerns compounds of formula (1), wherein A is a group of formula (a) or (b), wherein: R represents a hydrogen or halogen atom, a —S(O) z (C 1 -C 4 )Alk wherein z is 0, 1 or 2, a —NHSO 2 (C 1 -C 4 )Alk, —SO 2 NH(C 1 -C 4 )Alk, —NHSO 2 —(C 1 -C 4 )Alk-phenyl or —NHSO 2 -phenyl group, said phenyl capable of bearing a halogen atom, a (C 1 -C 4 )Alk group or a (C 1 -C 6 )alkoxy group; R 1 represents a hydrogen atom or a —(C 1 -C 4 )Alk, —CO(C 1 -C 4 )Alk, —(C 1 -C 4 )Alk-phenyl or —CO-phenyl group, said phenyl capable of bearing a halogen atom or a —(C 1 -C 4 )Alk or (C 1 -C 6 )alkoxy group; R 2 is a hydrogen atom, a —SO 2 (C 1 -C 4 )Alk, —SO 2 —(C 1 -C 4 )Alk-phenyl, —SO 2 -phenyl group, or a —(C 1 -C 4 )Alk group; X completes a saturated or unsaturated cycle of 5 to 8 atoms, capable of bearing one or two —(C 1 -C 4 )Alk groups and/or two carbonyl groups; R 3 and R′ 3 represent each independently a hydrogen or halogen atom, a —(C 1 -C 6 )Alk, hydroxy, —CN, —(C 1 -C 6 )alkoxy, —COR 4 or Y—CR 8 R 9 —COR 4 group; Y represents O or CH 2 ; R 4 represents a hydroxy, (C 1 -C 6 )alkoxy or —NR 5 R 6 group; R 5 and R 6 independently represent a hydrogen atom, a —(C 1 -C 4 )Alk, group, aryl or heteroaryl optionally substituted by a R 7 group, aralkyl or heteroaralkyl optionally substituted by a R 7 group; or R 5 and R 6 , with the nitrogen atom which bears them, form a saturated or unsaturated cycle of 5 to 7 atoms optionally substituted by a R 7 group; and R 7 represents a hydrogen or halogen atom, a hydroxy, —(C 1 -C 4 )Alk, —(C 1 -C 6 )alkoxy, —NH(C 1 -C 4 )Alk, —N(C 1 -C 4 )Alk 2 , —COO(C 1 -C 4 )Alk, aralkyl or heteroaryl group; R 8 and R 9 independently represent a hydrogen atom or a —(C 1 -C 4 )Alk group; their salts or solvates, the pharmaceutical compositions containing them, a method for preparing them and synthesis intermediates.

  本发明涉及公式（1）的化合物，其中A是公式（a）或（b）的基团，其中：R代表氢或卤素原子，-S（O）z（C1-C4）Alk，其中z为0，1或2，-NHSO2（C1-C4）Alk，-SO2NH（C1-C4）Alk，-NHSO2-（C1-C4）Alk-苯基或-NHSO2-苯基，所述苯基能够承载卤素原子，（C1-C4）Alk基团或（C1-C6）alkoxy基团；R1代表氢原子或-（C1-C4）Alk，-CO（C1-C4）Alk，-（C1-C4）Alk-苯基或-CO-苯基，所述苯基能够承载卤素原子或-（C1-C4）Alk或（C1-C6）alkoxy基团；R2是氢原子，-SO2（C1-C4）Alk，-SO2-（C1-C4）Alk-苯基，-SO2-苯基或-（C1-C4）Alk基团；X完成一个饱和或不饱和的5至8个原子环，能够承载一个或两个-（C1-C4）Alk基团和/或两个羰基基团；R3和R′3各自独立地代表氢或卤素原子，-（C1-C6）Alk，羟基，-CN，-（C1-C6）alkoxy，-COR4或Y-CR8R9-COR4基团；Y代表O或CH2；R4代表羟基，（C1-C6）alkoxy或-NR5R6基团；R5和R6独立地代表氢原子，-（C1-C4）Alk基团，芳基或杂环芳基，可选地被R7基团取代，芳基烷基或杂环芳基烷基，可选地被R7基团取代；或R5和R6与它们所承载的氮原子形成一个饱和或不饱和的5到7个原子环，可选地被R7基团取代；R7代表氢或卤素原子，羟基，-（C1-C4）Alk，-（C1-C6）alkoxy，-NH（C1-C4）Alk，-N（C1-C4）Alk2，-COO（C1-C4）Alk，芳基烷基或杂环芳基；R8和R9独立地代表氢原子或-（C1-C4）Alk基团；它们的盐或溶剂，含有它们的制药组合物，制备它们的方法和合成中间体。
• Synthesis and biological activity of new anti-inflammatory compounds containing the 1,4-benzodioxine and/or pyrrole system
  作者：Y. Harrak、G. Rosell、G. Daidone、S. Plescia、D. Schillaci、M.D. Pujol

  DOI：10.1016/j.bmc.2007.04.050

  日期：2007.7

  A series of substituted derivatives containing the 1,4-benzodioxine or pyrrole nucleus are described. All the newly synthesized compounds were examined for their in vitro and in vivo anti-inflammatory activity. Several derivatives, including (S)-2, 14 and 17, showed more anti-inflammatory activity in vivo in these assays (rat paw oedema induced by carrageenan) than the known classical anti-inflammatory agent ibuprofen, whereas other compounds like 1 were equipotent to ibuprofen. Compound 17 was the most outstanding derivative because of its remarkable in vivo anti-inflammatory activity. In this paper, we examine and discuss the structure-activity relationships and anti-inflammatory activities of these compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• BRUKSHTUS, A. B.;RAMANAUSKAS, YU. YU.;LAUZHIKENE, N. A., NAUCH. TR. VUZOV LITSSR. XIMIYA. I XIM. TEXNOL., 30,(1988) S. 62-65
  作者：BRUKSHTUS, A. B.、RAMANAUSKAS, YU. YU.、LAUZHIKENE, N. A.

  DOI：——

  日期：——
• US7115780B2
  申请人：——

  公开号：US7115780B2

  公开（公告）日：2006-10-03