DHP-361 | 791-37-7

• 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: DHP-361
• 英文别名: 4-(N,N-dimethylamino)-1,1-diphenylbutan-1-ol；4-dimethylamino-1,1-diphenylbutan-1-ol；4-dimethylamino-1,1-diphenyl-butan-1-ol；DPH-361；α-(3-Dimethylaminopropyl)-benzhydrol；1-Dimetylamino-4-hydroxy-4,4-diphenyl-butan；4-(Dimethylamino)-1,1-diphenylbutan-1-ol
• CAS: 791-37-7
• 化学式: C₁₈H₂₃NO
• 分子量: 269.387
• InChiKey: WSCHDJUSBOEJSL-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123.5 °C
• 沸点：
  121-122 °C
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  DHP-361 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以78%的产率得到(4,4-二苯基-丁-3-烯基)-二甲基-胺
  参考文献：
  名称：

  [EN] NOVEL TRICYCLIC, BICYCLIC, MONOCYCLIC, AND ACYCLIC AMINES AS POTENT SODIUM CHANNEL BLOCKING AGENTS
  [FR] NOUVEAUX AMINES TRICYCLIQUES, BICYCLIQUES, MONOCYCLIQUES ET ACYCLIQUES UTILES COMME AGENTS BLOQUANTS PUISSANTS DES CANAUX DE SODIUM

  摘要：

  公开号：

  WO2006023757A3
• 作为产物：
  描述：

  1-Dimethylamino-4-hydroxy-4,4-diphenylbut-2-in 在 乙醇 、 镍 作用下， 50.0 ℃ 、5.39 MPa 条件下， 生成 DHP-361
  参考文献：
  名称：

  1,1-diphenyl-4-tert.-amino-2-butyne-1-ols

  摘要：

  公开号：

  US02584429A1

文献信息

• Holm,T., Acta Chemica Scandinavica (1947), 1963, vol. 17, p. 2437 - 2443
  作者：Holm,T.

  DOI：——

  日期：——
• Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2
  作者：Debjani P. Hudgens、Catherine Taylor、Timothy W. Batts、Manoj K. Patel、Milton L. Brown

  DOI：10.1016/j.bmc.2006.09.010

  日期：2006.12

  The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [H-3]-BTX binding site and sodium currents of hNa(v)1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Na(v)1.2 currents at 10 mu M, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNa(v)1.2 activity and modification of the amine portion is detrimental to sodium channel block. (c) 2006 Elsevier Ltd. All rights reserved.
• Miodownik, A.; Kreisberger, J.; Nussim, M., Synthetic Communications, 1981, vol. 11, # 3, p. 241 - 246
  作者：Miodownik, A.、Kreisberger, J.、Nussim, M.、Avnir, D.

  DOI：——

  日期：——
• Tuning the Reducing Properties of 1,2-Diaryl-1,2-disodiumethanes
  作者：Ugo Azzena、Luisa Pisano、Sabrina Antonello、Flavio Maran

  DOI：10.1021/jo901183x

  日期：2009.11.6

  We investigated the reducing properties of a series of 1,2-diaryl-1,2-disodiumethanes by means of equilibration reactions. The electron-donor power of these vic-diorganometals is strongly affected by the nature of substituents present either on the aromatic ring(s) or on the carbanionic centers, and it can be correlated with their ability to delocalize the arylmethyl carbanions. These findings are supported by electrochemical analysis of the reduction behavior of the parent 1,2-diarylalkene. Applications of these results to the reduction of selected substrates are described.
• Regioselective hydroaminomethylation of 1,1-diaryl-allyl-alcohols: a new access to 4,4-diarylbutylamines
  作者：Andreas Schmidt、Mauro Marchetti、Peter Eilbracht

  DOI：10.1016/j.tet.2004.09.058

  日期：2004.12

  Pharmacologically active 4,4-diarylbutylamines like Fluspirilene and 4-amino-1,1-diarylbutan-1-ols like Difenidol were prepared in high yields via rhodium catalysed hydroaminomethylation of 1,1-diaryl-allylalcohols. Conversion of these olefins with carbon monoxide, hydrogen and secondary amines proceeds with complete regioselectivity. This group can easily be removed under acidic and hydrogenating conditions, enabling the transformation of 4-amino-1,1-diarylbutan-1-ols to 4,4-diarylbutylamines in high yields. Thus Fluspirilene was synthesised in 88% yield in four steps starting from commercially available materials. (C) 2004 Elsevier Ltd. All rights reserved.