8-phthalimidooctan-2-one | 85328-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 8-phthalimidooctan-2-one
• 英文别名: 2-(7-oxooctyl)isoindoline-1,3-dione；N-(7-oxo-octyl)-phthalimide；N-(7-Oxo-octyl)-phthalimid；2-(7-oxooctyl)isoindole-1,3-dione
• CAS: 85328-47-8
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: CKHACJQHTLEVBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-phthalimidooctan-2-one 在 光气 、 高氯酸 、 potassium carbonate 、 对甲苯磺酸 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 11.0h， 生成 4-(diphenylmethyl)-1-<<(7-oxooctyl)imino>methyl>piperidine
  参考文献：
  名称：

  Antisecretory activity of human, dog, and rat metabolites of fenoctimine

  摘要：

  Fenoctimine (1a), a nonanticholinergic inhibitor of gastric acid secretion in dogs and rats, was evaluated as a gastric antisecretory agent in humans. In humans it exhibited weak antisecretory activity and caused anticholinergic-like side effects such as dry mouth and nasal passages. Studies of the metabolic fate of fenoctimine in humans, dogs, and rats provided structures of the resultant metabolites. These were synthesized and tested for antisecretory and anticholinergic activity. The human metabolites were all less active than fenoctimine as antisecretory agents, and some displayed significant anticholinergic activity. These results suggest that the unexpectedly weak effect of fenoctimine as a gastric antisecretory agent in humans, as well as anticholinergic effects, may be due to its extensive metabolism, which is different from that seen in dog and rat.

  DOI：

  10.1021/jm00388a025
• 作为产物：
  描述：

  N-(5-溴戊基)邻苯二甲酰亚胺 在 盐酸 、 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 6.5h， 生成 8-phthalimidooctan-2-one
  参考文献：
  名称：

  Antisecretory activity of human, dog, and rat metabolites of fenoctimine

  摘要：

  Fenoctimine (1a), a nonanticholinergic inhibitor of gastric acid secretion in dogs and rats, was evaluated as a gastric antisecretory agent in humans. In humans it exhibited weak antisecretory activity and caused anticholinergic-like side effects such as dry mouth and nasal passages. Studies of the metabolic fate of fenoctimine in humans, dogs, and rats provided structures of the resultant metabolites. These were synthesized and tested for antisecretory and anticholinergic activity. The human metabolites were all less active than fenoctimine as antisecretory agents, and some displayed significant anticholinergic activity. These results suggest that the unexpectedly weak effect of fenoctimine as a gastric antisecretory agent in humans, as well as anticholinergic effects, may be due to its extensive metabolism, which is different from that seen in dog and rat.

  DOI：

  10.1021/jm00388a025

文献信息

• Methylene C(sp³)–H Arylation of Aliphatic Ketones Using a Transient Directing Group
  作者：Kai Hong、Hojoon Park、Jin-Quan Yu

  DOI：10.1021/acscatal.7b02905

  日期：2017.10.6

  Palladium-catalyzed methylene β-C(sp3)–H arylation of aliphatic ketones using a transient directing group is developed. The use of α-benzyl β-alanine directing group that forms a six-membered chelation with palladium is crucial for promoting the methylene C(sp3)–H bond activation.

  开发了使用瞬态导向基团的钯催化脂族酮的亚甲基β-C（sp 3）–H芳基化反应。与钯形成六元螯合的α-苄基β-丙氨酸引导基团的使用对于促进亚甲基C（sp 3）–H键的活化至关重要。
• Temporal separation of catalytic activities allows anti-Markovnikov reductive functionalization of terminal alkynes
  作者：Le Li、Seth B. Herzon

  DOI：10.1038/nchem.1799

  日期：2014.1

  There is currently great interest in the development of multistep catalytic processes in which one or several catalysts act sequentially to rapidly build complex molecular structures. Many enzymes—often the inspiration for new synthetic transformations—are capable of processing a single substrate through a chain of discrete, mechanistically distinct catalytic steps. Here, we describe an approach to emulate the efficiency of these natural reaction cascades within a synthetic catalyst by the temporal separation of catalytic activities. In this approach, a single catalyst exhibits multiple catalytic activities sequentially, allowing for the efficient processing of a substrate through a cascade pathway. Application of this design strategy has led to the development of a method to effect the anti-Markovnikov (linear-selective) reductive functionalization of terminal alkynes. The strategy of temporal separation may facilitate the development of other efficient synthetic reaction cascades. Multifunctional catalysts typically process substrates and intermediates concurrently. Here, a strategy is described to separate catalytic activities in the time domain (temporal separation). Application of this strategy has led to the development of a method to effect the anti-Markovnikov reductive functionalization of terminal alkynes; such an approach may facilitate the development of other synthetic reaction cascades.

  目前，发展多步催化过程备受关注，其中一个或多个催化剂按顺序作用，以快速构建复杂分子结构。许多酶——通常是新合成转化的灵感来源——能够通过一系列离散的、机制上不同的催化步骤处理单一底物。在这里，我们描述了一种通过催化活性的时间分离来模拟这些自然反应级联的效率的方法。在这种方法中，单一催化剂按顺序展现多种催化活性，从而允许有效地通过级联路径处理底物。该设计策略的应用促成了一种方法，以实现末端炔烃的反马尔科夫尼科夫（线性选择性）还原官能化。时间分离的策略可能会促进其他高效合成反应级联的发展。多功能催化剂通常同时处理底物和中间体。在这里，描述了一种在时间领域分离催化活性的策略（时间分离）。该策略的应用促成了一种方法，以实现末端炔烃的反马尔科夫尼科夫还原官能化；如此方法可能会促进其他合成反应级联的发展。
• Nickel-Catalyzed C(sp³)–C(sp³) Cross-Electrophile Coupling of In Situ Generated NHP Esters with Unactivated Alkyl Bromides
  作者：Kai Kang、Daniel J. Weix

  DOI：10.1021/acs.orglett.2c00805

  日期：2022.4.22

  The formation of C(sp3)–C(sp3) bonds by cross-coupling remains a challenge in synthesis. Here, we demonstrate a two-step, one-pot protocol for the in situ generation of N-hydroxyphthalimide esters and their nickel-catalyzed cross-electrophile coupling with unactivated alkyl bromides for the construction of 1°/1 ° C(sp3)–C(sp3) bonds. The conditions tolerate an array of functional groups, and mechanistic

  通过交叉偶联形成C(sp 3 )–C(sp 3 )键仍然是合成中的一个挑战。在这里，我们演示了一种两步一锅法，用于原位生成N-羟基邻苯二甲酰亚胺酯及其镍催化的交叉亲电子试剂与未活化的烷基溴的偶联，以构建 1°/1°C(sp 3 ) –C(sp 3 ) 键。该条件可耐受一系列官能团，机理研究表明两种底物在反应过程中均转化为烷基自由基。
• Antisecretory 4-diphenylmethyl-1-[(oxoalkyl)imino]methyl-piperidines and
  申请人：McNeilab, Inc.

  公开号：US04370335A1

  公开（公告）日：1983-01-25

  4-Diphenyl-1-[(oxo and oxo-related alkyl)imino]methyl-piperidine derivatives are disclosed which are useful for the inhibition of gastric acid secretion.

  本文披露了4-二苯基-1-[(氧化和氧化相关烷基)亚胺基]甲基-哌啶衍生物，其可用于抑制胃酸分泌。
• 4-Diphenylmethyl-1-(oxoalkyl)imino)methyl-piperidines and their derivatives
  申请人：McNeilab, Inc.

  公开号：EP0087853A2

  公开（公告）日：1983-09-07

  4-diphenyl-1-[(oxo and oxo-related alkyl)imino]methylpiperidine derivatives are disclosed which are useful for the inhibition of gastric acid secretion.

  本研究公开了可用于抑制胃酸分泌的 4-二苯基-1-[（氧代和氧代相关烷基）亚氨基]甲基哌啶衍生物。