atropine | 111295-08-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: atropine
• 英文别名: N-Ethylnoratropin；(8-Ethyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate
• CAS: 111295-08-0；737703-66-1；693209-51-7
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: GTQYBFRPQLLPQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium cyanide 、 atropine 在 氧气 、 rose bengal 作用下， 以 水 、 乙腈 为溶剂， 反应 0.05h， 以72.5%的产率得到8-(cyanomethyl)-8-azabicyclo[3.2.1]oct-3-yl-2-phenyl-3-hydroxypropanoate
  参考文献：
  名称：

  Sunflow：阳光在简单的微毛细管反应器中驱动快速和绿色的光化学流动反应 - 在光氧化还原和 H 原子转移化学中的应用

  摘要：

  “Sunflow”——连续流动模式下的微毛细管反应器与作为可想象的最可持续能源的阳光相结合，应用于一系列光氧化还原和 H 原子转移反应，使其既快速又环保。

  DOI：

  10.1002/ejoc.201601394
• 作为产物：
  描述：

  DL-托品酸 在 盐酸 、 氯化亚砜 作用下， 反应 30.5h， 生成 atropine
  参考文献：
  名称：

  Differential analgesic activity of the enantiomers of atropine derivatives does not correlate with their muscarinic subtype selectivity

  摘要：

  The enantiomers of several tropic and p-substituted tropic acid esters related to atropine obtained by esterification under non-racemizing conditions after resolution of the corresponding racemic acids [(+)- and (-)-18, (+)- and (-)-19] are reported. They were tested in vitro on muscarinic subtype receptors and in vivo for their analgesic activity on mice. As in the case of the lead compound, R-(+)-hyoscyamine, these substances show enantioselectivity in analgesic tests, the eutomers being the R-(+) or R-(+)-p-substituted tropic acid derivatives. However, this property, which is a consequence of increased central release of ACh, seems unrelated to muscarinic subtype selectivity insofar as the compounds are unable to discriminate muscarinic subtype receptors. A possible explanation of these results which does not involve subtype selectivity is proposed, based on the recently developed concept of inverse agonism.

  DOI：

  10.1016/s0223-5234(97)83285-0

文献信息

• Differential analgesic activity of the enantiomers of atropine derivatives does not correlate with their muscarinic subtype selectivity
  作者：S Dei、A Bartolini、C Bellucci、C Ghelardini、F Gualtieri、D Manetti、M.N. Romanelli、S Scapecchi、E Teodori

  DOI：10.1016/s0223-5234(97)83285-0

  日期：1997.7

  The enantiomers of several tropic and p-substituted tropic acid esters related to atropine obtained by esterification under non-racemizing conditions after resolution of the corresponding racemic acids [(+)- and (-)-18, (+)- and (-)-19] are reported. They were tested in vitro on muscarinic subtype receptors and in vivo for their analgesic activity on mice. As in the case of the lead compound, R-(+)-hyoscyamine, these substances show enantioselectivity in analgesic tests, the eutomers being the R-(+) or R-(+)-p-substituted tropic acid derivatives. However, this property, which is a consequence of increased central release of ACh, seems unrelated to muscarinic subtype selectivity insofar as the compounds are unable to discriminate muscarinic subtype receptors. A possible explanation of these results which does not involve subtype selectivity is proposed, based on the recently developed concept of inverse agonism.
• Sunflow: Sunlight Drives Fast and Green Photochemical Flow Reactions in Simple Microcapillary Reactors - Application to Photoredox and H-Atom-Transfer Chemistry
  作者：Alexander M. Nauth、Alexander Lipp、Benjamin Lipp、Till Opatz

  DOI：10.1002/ejoc.201601394

  日期：2017.4.18

  “Sunflow“ – The combination of a microcapillary reactor in continuous flow mode with sunlight as the most sustainable energy source imaginable was applied to a range of photoredox and H-atom-transfer reactions making them both fast and green.

  “Sunflow”——连续流动模式下的微毛细管反应器与作为可想象的最可持续能源的阳光相结合，应用于一系列光氧化还原和 H 原子转移反应，使其既快速又环保。