(3S,4R)-3-[(1,3-苯并二氧杂环戊烯-5-基氧基)甲基]-1-甲基-4-苯基哌啶 | 324023-99-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (3S,4R)-3-[(1,3-苯并二氧杂环戊烯-5-基氧基)甲基]-1-甲基-4-苯基哌啶
• 英文名称: (-)-trans-1-methyl-3-(3,4-methylenedioxyphenoxymethyl)-4-phenylpiperidine
• 英文别名: (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-1-methyl-4-phenylpiperidine；(3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-1-methyl-4-phenylpiperidine
• CAS: 324023-99-6
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: OVUNPIXRLQMWHL-WMZOPIPTSA-N

物化性质

• 沸点：
  445.3±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-[(1,3-苯并二氧杂环戊烯-5-基氧基)甲基]-1-甲基-4-苯基哌啶 在 lithium aluminium tetrahydride 、 溴化氰 作用下， 生成 (-)-trans-3-(3,4-methylenedioxyphenoxymethyl)-4-phenylpiperidine hydrochloride
  参考文献：
  名称：

  Synthesis and 5HT Modulating Activity of Stereoisomers of 3-Phenoxymethyl-4-phenylpiperidines.

  摘要：

  A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or alpha-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT(2A) and 5HT(2C) receptors.

  DOI：

  10.3891/acta.chem.scand.50-0164
• 作为产物：
  描述：

  (-)-trans-3-hydroxymethyl-1-methyl-4-phenylpiperidine 在 氯化亚砜 、 芝麻酚 、 sodium hydride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 (3S,4R)-3-[(1,3-苯并二氧杂环戊烯-5-基氧基)甲基]-1-甲基-4-苯基哌啶
  参考文献：
  名称：

  Synthesis and 5HT Modulating Activity of Stereoisomers of 3-Phenoxymethyl-4-phenylpiperidines.

  摘要：

  A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or alpha-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT(2A) and 5HT(2C) receptors.

  DOI：

  10.3891/acta.chem.scand.50-0164

文献信息

• Light‐Driven Hydrodefluorination of Electron‐Rich Aryl Fluorides by an Anionic Rhodium‐Gallium Photoredox Catalyst
  作者：James T. Moore、Michael J. Dorantes、Zihan Pengmei、Timothy M. Schwartz、Jacob Schaffner、Samantha L. Apps、Carlo A. Gaggioli、Ujjal Das、Laura Gagliardi、David A. Blank、Connie C. Lu

  DOI：10.1002/anie.202205575

  日期：2022.10.17

  Incredibly strong C−X bonds such as those in aryl fluorides are catalytically cleaved using an anionic Rh−Ga photoredox catalyst. Excitation of the bimetallic complex with violet light generates a potent photoreductant that is capable of single-electron transfer to even electron-rich aryl fluorides that ultimately results in substrate hydrodefluorination.

  使用阴离子 Rh-Ga 光氧化还原催化剂催化裂解非常强的 C-X 键，例如芳基氟化物中的 C-X 键。用紫光激发双金属络合物会产生一种有效的光还原剂，这种光还原剂能够将单电子转移到甚至富含电子的芳基氟化物，最终导致底物加氢脱氟。