4-[1-(3-methoxyphenyl)benzylidene]-1-(methylsulfonyl)-piperidine | 916976-43-7

• 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: 4-[1-(3-methoxyphenyl)benzylidene]-1-(methylsulfonyl)-piperidine
• 英文别名: 1-(Methanesulfonyl)-4-[(3-methoxyphenyl)(phenyl)methylidene]piperidine；4-[(3-methoxyphenyl)-phenylmethylidene]-1-methylsulfonylpiperidine
• CAS: 916976-43-7
• 化学式: C₂₀H₂₃NO₃S
• 分子量: 357.474
• InChiKey: DTMRYIPBDDEDBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[1-(3-methoxyphenyl)benzylidene]-1-(methylsulfonyl)-piperidine 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以82%的产率得到5-(3-Methoxyphenyl)-1-methylsulfonyl-5-phenylazepan-4-one
  参考文献：
  名称：

  Synthesis of diarylazepan-4-ones

  摘要：

  Synthesis of several 3,3-diarylazepan-4-ones and 5,5-diarylazepan-4-ones has been established starting from two tetrasubstituted olefins, which is derived from commercially available piperidine-3-carboxylic acid ethyl ester and piperidine-4-carboxylic acid ethyl ester. The single isomer with the structural skeleton of 3,3-diarylazepan-4-one and 5,5-diarylazepan-4-one is constructed in two functional group transformations of Grignard addition/dehydration and epoxidation/pinacol rearrangement. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.072
• 作为产物：
  描述：

  1-(甲基磺酰基)-4-哌啶羧酸乙酯 在 lithium aluminium tetrahydride 、 Celite 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-[1-(3-methoxyphenyl)benzylidene]-1-(methylsulfonyl)-piperidine
  参考文献：
  名称：

  Synthesis of diarylazepan-4-ones

  摘要：

  Synthesis of several 3,3-diarylazepan-4-ones and 5,5-diarylazepan-4-ones has been established starting from two tetrasubstituted olefins, which is derived from commercially available piperidine-3-carboxylic acid ethyl ester and piperidine-4-carboxylic acid ethyl ester. The single isomer with the structural skeleton of 3,3-diarylazepan-4-one and 5,5-diarylazepan-4-one is constructed in two functional group transformations of Grignard addition/dehydration and epoxidation/pinacol rearrangement. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.072

文献信息

• BF₃-OEt₂-Mediated Rearrangement of (4-Phenylpiperidin-4-Yl)-Arylmethanols
  作者：Meng-Yang Chang、Tsun-Cheng Wu、Shiang-Tsern Lin

  DOI：10.1002/jccs.200800070

  日期：2008.4

  Synthesis of several 4-benzhydrylidenepiperidine analogs has been established starting from different (4-phenylpiperidin-4-yl)-arylmethanols via boron trifluoride etherate mediated rearrangement. The possible rearranged mechanism was proposed. Boron trifluoride etherate-mediated rearrangement of the related derivatives was also examined. It presents a novel rearrangement reaction catalyzed by boron

  已经建立了从不同的 (4-苯基哌啶-4-基)-芳基甲醇通过三氟化硼醚合物介导的重排开始合成几种 4-二苯甲基哌啶类似物。提出了可能的重排机制。还检查了三氟化硼醚合物介导的相关衍生物的重排。提出了一种新型的三氟化硼醚合物催化的重排反应，拓宽了应用范围。
• CAN-mediated rearrangement of 4-benzhydrylidenepiperidines
  作者：Meng-Yang Chang、Tsun-Cheng Wu、Chun-Yu Lin、Ching-Yi Hung

  DOI：10.1016/j.tetlet.2006.09.068

  日期：2006.11

  Several 1-substituted phenyl-(4-phenylpiperidin-4-yl)methanones are synthesized in modest overall yields starting from the reaction of different 1-substituted 4-benzhydrylidenepiperidines via CAN-mediated rearrangement. This facile strategy was also used to synthesize meperidine analog. (c) 2006 Elsevier Ltd. All rights reserved.