(S)-莫达非尼羧酸酯甲酯 | 865811-65-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-莫达非尼羧酸酯甲酯
• 中文别名: 莫达非尼羧酸甲酯
• 英文名称: (S)-(+)-methyl (diphenylmethanesulfinyl)-acetate
• 英文别名: (S)-methyl 2-(diphenylmethylsulfinyl)acetate；(S)-methyl 2-(benzhydrylsulfinyl)acetate；Methyl [(S)-diphenylmethanesulfinyl]acetate；methyl 2-[(S)-benzhydrylsulfinyl]acetate
• CAS: 865811-65-0
• 化学式: C₁₆H₁₆O₃S
• 分子量: 288.367
• InChiKey: JFMZFATUMFWKEA-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-莫达非尼羧酸酯甲酯 在 乙酰氯 、 potassium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以95%的产率得到methyl 2-(benzhydrylthio)acetate
  参考文献：
  名称：

  Towards a Robust and Reliable Method for the Reduction of Functionalized Sulfoxides

  摘要：

  Several functionalized sulfoxides in the modafinil series, which bear another reducible function, were chemoselectively reduced to thioethers using the KI/AcCl system.

  DOI：

  10.1021/op800088x
• 作为产物：
  描述：

  2-[(二苯基甲基)亚砜]乙酸乙酯 在 sodium hydroxide 、 R(+)-alpha-甲基苄胺 、 水 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 1.0h， 生成 (S)-莫达非尼羧酸酯甲酯
  参考文献：
  名称：

  Synthesis and determination of the absolute configuration of the enantiomers of modafinil

  摘要：

  The asymmetric synthesis of both enantiomers of modafinil, a unique CNS stimulant with a reduced abuse liability, is described. This approach effectively prepares modafinil on a multigram scale in several steps from benzhydrol. The described synthetic route has also been used to produce the more water soluble analogue, adrafinil. X-ray crystallographic analysis on (diphenylmethanesulfinyl)acetic acid has determined the absolute configuration to be R. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.039

文献信息

• SARs at the Monoamine Transporters for a Novel Series of Modafinil Analogues
  作者：Jianjing Cao、Thomas E. Prisinzano、Oluyomi M. Okunola、Theresa Kopajtic、Matthew Shook、Jonathan L. Katz、Amy Hauck Newman

  DOI：10.1021/ml1002025

  日期：2011.1.13

  A series of modafinil (1) analogues was synthesized wherein 1) para-halo-substitutents were added to the aryl rings, 2) the sulfoxide function was removed, and 3) the primary amide group was replaced with secondary and tertiary amides and amines to investigate the effects of these chemical modifications on DAT, SERT and NET binding. In addition, the locomotor-stimulant effects in mice of (+/-)-modafinil

  合成了一系列莫达非尼（1）类似物，其中1）将对卤代取代基添加到芳环上，2）除去亚砜官能团，3）伯酰胺基被仲和叔酰胺和胺取代，得到研究这些化学修饰对DAT，SERT和NET结合的影响。另外，将（+/-）-莫达非尼（1），其R-和S-对映异构体及其对氯亚磺酰基乙酰胺类似物（5c）对小鼠的运动刺激作用与可卡因进行了比较。
• [EN] ION PAIR CATALYSIS OF TUNGSTATE AND MOLYBDATE<br/>[FR] CATALYSE PAR PAIRE D'IONS DE TUNGSTATE ET DE MOLYBDATE
  申请人：UNIV NANYANG TECH

  公开号：WO2017164813A1

  公开（公告）日：2017-09-28

  D The present invention relates to ion pair catalysts (I) comprising the cationic bisguanidinium ligand (A) and diperoxomolybdate anion (B). The present invention also relates to ion pair catalysts (III) comprising the cationic bisguanidinium ligand (C) and peroxotungstate anion (D). It further relates to the use of the said catalysts in the manufacture of enantiomerically enriched sulfoxides.

  本发明涉及离子对催化剂(I)，包括阳离子双胍基配体(A)和过氧钼酸根离子(B)。本发明还涉及离子对催化剂(III)，包括阳离子双胍基配体(C)和过氧钨酸根离子(D)。此外，本发明还涉及所述催化剂在合成对映富集亚砜中的应用。
• Ion pair catalysis of tungstate and molybdate
  申请人：Nanyang Technological University

  公开号：US10710061B2

  公开（公告）日：2020-07-14

  D The present invention relates to ion pair catalysts (I) comprising the cationic bisguanidinium ligand (A) and diperoxomolybdate anion (B). The present invention also relates to ion pair catalysts (III) comprising the cationic bisguanidinium ligand (C) and peroxotungstate anion (D). It further relates to the use of the said catalysts in the manufacture of enantiomerically enriched sulfoxides.

  D 本发明涉及由阳离子双胍配体（A）和二氧钼酸阴离子（B）组成的离子对催化剂（I）。本发明还涉及由阳离子双胍配体（C）和过氧钨酸盐阴离子（D）组成的离子对催化剂（III）。本发明还涉及上述催化剂在制造对映体富集的硫氧化物中的用途。
• Preparation of Asymmetric Phase-transfer Catalyst, 1,4-Bis((4S,5S)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium chloride
  作者：Esther Cai Xia Ang

  DOI：10.15227/orgsyn.097.0274

  日期：——
• Asymmetric synthesis of modafinil and its derivatives by enantioselective oxidation of thioethers: comparison of various methods including synthesis in ionic liquids
  作者：James Ternois、Frédéric Guillen、Jean-Christophe Plaquevent、Gérard Coquerel

  DOI：10.1016/j.tetasy.2007.11.031

  日期：2007.12

  The oxidation of 2-(benzhydrylthio)acetic acid and its derivatives was performed with various catalytic and stoichiometric enantioselective reagents, the best results being obtained with stoichiometric chiral oxaziridine 5. The use of [bmim][PF6] as a solvent with 5 gave slightly higher yields and, in the case of the model compound thioanisole, a reversal of the enantioselectivity. (c) 2007 Elsevier Ltd. All rights reserved.