(1S,2S)-2-(4-fluorophenyl)-N-methoxy-N-methylcyclopropanecarboxamide | 1455028-46-2

• 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: (1S,2S)-2-(4-fluorophenyl)-N-methoxy-N-methylcyclopropanecarboxamide
• 英文别名: (1S,2S)-2-(4-fluorophenyl)-N-methoxy-N-methyl cyclopropanecarboxamide；(1S,2S)-2-(4-fluorophenyl)-N-methoxy-N-methylcyclopropane-1-carboxamide
• CAS: 1455028-46-2
• 化学式: C₁₂H₁₄FNO₂
• 分子量: 223.247
• InChiKey: XVNIFCWBPAUFNS-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-(4-fluorophenyl)-N-methoxy-N-methylcyclopropanecarboxamide 在 titanium(IV) isopropylate 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正庚烷 、 二乙胺 、 正戊烷 为溶剂， 反应 8.0h， 生成 1-((1S,2S)-2-(4-fluorophenyl)cyclopropyl)ethanamine HCl
  参考文献：
  名称：

  Positive Allosteric Modulators of MGLUR2

  摘要：

  该披露通常涉及到公式I的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物调节mGluR2受体，可能有助于治疗中枢神经系统的各种疾病。

  公开号：

  US20130245042A1
• 作为产物：
  描述：

  对氟肉桂酸 在 4-二甲氨基吡啶 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (1S,2S)-2-(4-fluorophenyl)-N-methoxy-N-methylcyclopropanecarboxamide
  参考文献：
  名称：

  Discovery and optimization of Lu AF58801, a novel, selective and brain penetrant positive allosteric modulator of alpha-7 nicotinic acetylcholine receptors: Attenuation of subchronic phencyclidine (PCP)-induced cognitive deficits in rats following oral administration

  摘要：

  In this Letter, we describe a chemical lead optimization campaign starting from a novel, weak alpha 7 nicotinic acetylcholine receptor positive allosteric modulator (PAM) hit from a HTS screen. Exploration of the structure-activity relationships for alpha 7 PAM potency, intrinsic hepatic clearance, the structure-property relationships for lipophilicity, and thermodynamic solubility, led to the identification of Lu AF58801: a potent, orally available, brain penetrant PAM of the alpha 7 nicotinic acetylcholine receptor, showing efficacy in a novel object recognition task in rats treated subchronically with phencyclidine (PCP). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.022

文献信息

• Stereoselective Synthesis of (Sulfonimidoyl)cyclopropanes with (<i>R</i> )-PhSO(NTs)CH₂ Cl and α,β-Unsaturated Weinreb Amides: Tuning the of Selectivity between C-Cl and C-S Bond Cleavage
  作者：Xiao Shen、Qinghe Liu、Wei Zhang、Jinbo Hu

  DOI：10.1002/ejoc.201501611

  日期：2016.2

  advantages of two chemical leads (cyclopropane and sulfoximine). However, their synthesis is limited, and the stereoselective synthesis of optically enriched (sulfonimidoyl)cyclopropanes still remains an unsolved task. Here we report the first stereoselective (sulfonimidoyl)cyclopropanation reaction using α,β-unsaturated Weinreb amides and (R)-PhSO(NTs)CH2Cl [(R)-1]. This reaction possesses a broad substrate

  （磺酰亚胺酰基）环丙烷由于结合了两种化学先导物（环丙烷和亚砜亚胺）的优点而成为特别受关注的主题。然而，它们的合成是有限的，光学富集（磺酰亚胺酰基）环丙烷的立体选择性合成仍然是一个悬而未决的任务。在这里，我们报告了使用 α,β-不饱和 Weinreb 酰胺和 (R)-PhSO(NTs)CH2Cl [(R)-1] 的第一个立体选择性（磺酰亚胺酰基）环丙烷化反应。该反应具有广泛的底物范围，产物可以很容易地转化为其他有用的含环丙基和/或含磺酰亚胺酰基的化合物。发现 Weinreb 酰胺基团和碱的抗衡阳离子对于选择性 C-Cl 键断裂很重要。
• Positive allosteric modulators of mGluR2
  申请人：Bristol-Myers Squibb Company

  公开号：US08765767B2

  公开（公告）日：2014-07-01

  The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds modulate the mGluR2 receptor and may be useful for the treatment of various disorders of the central nervous system.

  该披露通常涉及公式I的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物调节mGluR2受体，可能有助于治疗各种中枢神经系统的疾病。
• [EN] MONOFLUORO CYCLOPROPANE COMPOUND, AND PREPARATION METHOD AND USE THEREOF<br/>[FR] COMPOSÉ DE CYCLOPROPANE MONOFLUORÉ, ET SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION
  申请人：SHANGHAI INST ORGANIC CHEM

  公开号：WO2013159736A1

  公开（公告）日：2013-10-31

  公开了一种单氟代环丙烷类化合物及其制备方法和应用。单氟代环丙烷类化合物的结构如式I所示，式中，R1，R2，Ra，式II的定义如说明书中所述。还提供了一种简单有效的制备单氟代环丙烷类化合物的方法。该方法不仅能制备消旋的化合物，还可制备非消旋的化合物。单氟代环丙烷类化合物可进一步用于合成其他环丙烷衍生物。
• Picosecond radical kinetics. Rate constants for ring openings of 2-aryl-substituted cyclopropylcarbinyl radicals
  作者：Martin Newcomb、Seung-Yong Choi、Patrick H. Toy

  DOI：10.1139/cjc-77-5-6-1123

  日期：——

  The kinetics of ring openings of a series of eight (trans-2-arylcyclopropyl)methyl radicals (1) were studied by indirect kinetic methods using Barton's PTOC esters as radical precursors and reaction with PhSeH as the competition reaction. The substituents were CF3, F, Me, and OMe located on both the para and meta positions of the aromatic ring. Syntheses of the radical precursors and the products of the radical reactions are described. Kinetics were determined between -43 and 25 degrees C in four cases (CF, and OMe substituents) and at 0 and 25 degrees C in the other four cases. The rate constants at 25 degrees C ranged from 1.0 x 10(11) s(-1) (p-CH3) to 4.1 x 10(11) s(-1) (p-CF,). The relatively large acceleration of the p-CF3 group, ca. 2.5 times as fast as the parent system with Ar = Ph, correlates well with Adam's Delta D substituent parameters but not with other radical substituent parameters. These calibrated radical rearrangements provide a new set of ultrafast reactions that can be applied in mechanistic probe studies.
• POSITIVE ALLOSTERIC MODULATORS OF MGLUR2
  申请人：Bristol-Myers Squibb Company

  公开号：EP2825538B1

  公开（公告）日：2016-06-01