N,N-dimethyl-3-oxo-(3-pyridinyl)-1-propanamine hydrochloride | 6293-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-dimethyl-3-oxo-(3-pyridinyl)-1-propanamine hydrochloride
• 英文别名: 3-dimethylamino-1-[3]pyridyl-propan-1-one; monohydrochloride；3-Dimethylamino-1-[3]pyridyl-propan-1-on; Monohydrochlorid；3-(Dimethylamino)-1-pyridin-3-ylpropan-1-one;hydrochloride
• CAS: 6293-82-9
• 化学式: C₁₀H₁₄N₂O*ClH
• 分子量: 214.695
• InChiKey: ASICDQVBJBJREI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-3-oxo-(3-pyridinyl)-1-propanamine hydrochloride 在 镍 氨 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 生成 麦司明
  参考文献：
  名称：

  部分烟草生物碱的对映选择性合成

  摘要：

  描述了通过 3-乙酰基吡啶 (1) 的甲硅烷基烯醇醚制备肌胺 (6) 的改进方法。6 与 N-(苄氧羰基)-L-脯氨酸/NaBH4 的手性还原和甲酰化导致 (R)-N-甲酰降烟碱 (8) (35 % ee) 进而转化为 (R)-降烟碱 (11) 和(R)-尼古丁 (10)。

  DOI：

  10.1002/ardp.19883210314
• 作为产物：
  描述：

  在 盐酸 作用下， 生成 N,N-dimethyl-3-oxo-(3-pyridinyl)-1-propanamine hydrochloride
  参考文献：
  名称：

  部分烟草生物碱的对映选择性合成

  摘要：

  描述了通过 3-乙酰基吡啶 (1) 的甲硅烷基烯醇醚制备肌胺 (6) 的改进方法。6 与 N-(苄氧羰基)-L-脯氨酸/NaBH4 的手性还原和甲酰化导致 (R)-N-甲酰降烟碱 (8) (35 % ee) 进而转化为 (R)-降烟碱 (11) 和(R)-尼古丁 (10)。

  DOI：

  10.1002/ardp.19883210314

文献信息

• 2-Sulfinyl-pentan-1,5-dione aus β-Oxosulfoxiden
  作者：Paul Messinger、Conrad Kunick

  DOI：10.1002/ardp.19853181116

  日期：——

  Synthese de diaryl-1,5 methanesulfinyl-2 pentanediones-1,5 par reaction de β-cetosulfoxydes avec des dimethylamino-3 propiophenones

  β-cetosulfoxydes avec des dimethylamino-3 propiophenones 反应合成二芳基-1,5-methanesulfinyl-2-pentanediones-1,5
• 2-(3-Aryl-3-oxopropen-1-yl)-9-<i>tert</i>-butyl-paullones: A New Antileishmanial Chemotype
  作者：Christina Reichwald、Orly Shimony、Ute Dunkel、Nina Sacerdoti-Sierra、Charles L. Jaffe、Conrad Kunick

  DOI：10.1021/jm7012166

  日期：2008.2.1

  A screening program directed to find new agents against Leishmania donovani, the parasite causing visceral leishmaniasis, revealed that paullones attenuate the proliferation of axenic amastigotes. Because these structures were not active in a test system involving infected macrophages, a structure optimization campaign was carried out. Concomitant introduction of an unsaturated side chain into the 2-position and a tert-butyl substituent into the 9-position of the parent scaffold led to compounds inhibiting also parasites dwelling in macrophages. By inclusion of the so elaborated scaffold into a chalcone substructure, the toxicity against uninfected host cells was significantly reduced. For the synthesis of this new compound class, a novel modification of the Heck-type palladium-catalyzed C,C-cross coupling strategy was used, employing a ketone Mannich base as precursor for the alkene reactant. The so-prepared compounds exhibited improved antileishmanial activity both on axenic amastigotes (GI(50) < 1 mu M) as well as on parasites in infected macrophages.
• A new Heck reaction modification using ketone Mannich bases as enone precursors: Parallel synthesis of anti-leishmanial chalcones
  作者：Christina Reichwald、Orly Shimony、Nina Sacerdoti-Sierra、Charles L. Jaffe、Conrad Kunick

  DOI：10.1016/j.bmcl.2008.01.112

  日期：2008.3

  A new Heck-type reaction for the synthesis of chalcones has been established using Mannich bases as enone precursors. The novel reaction proceeds rapidly in air atmosphere under ligandless conditions and can be adapted for library synthesis in a parallel reactor station. Screening of the synthesized chalcones revealed N-4-[(1E)-3-oxo-3-(3-pyridinyl)-1-propenyl]phenyl} benzamide (3f) to be a potent anti-leishmanial agent. (C) 2008 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of Some Nicotiana Alkaloids
  作者：Siavosh Mahboobi、Wolfgang Wiegrebe

  DOI：10.1002/ardp.19883210314

  日期：——

  A modified approach to myosmine (6) via a silyl enol ether of 3‐acetylpyridine (1) is described. Chiral reduction of 6 with N‐(benzyloxycarbonyl)‐L‐proline/NaBH4 and formylation leads to (R)‐N‐formylnornicotine (8) (35 % ee) which in turn is converted to (R)‐nornicotine (11) and (R)‐nicotine (10).

  描述了通过 3-乙酰基吡啶 (1) 的甲硅烷基烯醇醚制备肌胺 (6) 的改进方法。6 与 N-(苄氧羰基)-L-脯氨酸/NaBH4 的手性还原和甲酰化导致 (R)-N-甲酰降烟碱 (8) (35 % ee) 进而转化为 (R)-降烟碱 (11) 和(R)-尼古丁 (10)。