5-(2-氯苯基)-3,4-二氢-2H-吡咯 | 129540-25-6

• 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: 5-(2-氯苯基)-3,4-二氢-2H-吡咯
• 英文名称: 2-(2-chlorophenyl)-1-pyrroline
• 英文别名: 5-(2-chloro-phenyl)-3,4-dihydro-2H-pyrrole；5-(2-Chlorophenyl)-3,4-dihydro-2H-pyrrole
• CAS: 129540-25-6
• 化学式: C₁₀H₁₀ClN
• mdl: MFCD09037875
• 分子量: 179.649
• InChiKey: LRSMQEJORMBCBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(2-氯苯基)-3,4-二氢-2H-吡咯 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 2.0h， 生成 2-邻氯苯基四氢吡咯
  参考文献：
  名称：

  使用亚胺还原酶的药物相关手性2-芳基取代的吡咯烷的立体互补合成。

  摘要：

  探索天然存在的亚胺还原酶（IRED）的集合，确定了两个立体互补的IRED，它们对位阻2-芳基取代的吡咯啉的活性降低。使用（R）选择性ScIR和（S）选择性SvIR，以良好的收率（60-80％）立体互补合成了各种具有优异对映选择性（> 99％ee）的手性2-芳基取代的吡咯烷，证明了IRED的可行性用于产生药学上相关的手性2-芳基取代的吡咯烷中间体。

  DOI：

  10.1021/acs.orglett.0c00802
• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 邻氯苯甲酸乙酯 在 sodium hydride 作用下， 生成 5-(2-氯苯基)-3,4-二氢-2H-吡咯
  参考文献：
  名称：

  Pyrroloisoquinoline antidepressants. 3. A focus on serotonin

  摘要：

  A collection of hexahydropyrroloisoquinoline derivatives (1-22), which represent a class of compounds that inhibit the neuronal uptake of dopamine (DA), norepinephrine (NE), and serotonin (5-HT), was investigated in vivo for serotonin-potentiating properties in the mouse head-twitch and rat serotonin syndrome assays. The p-methylthio compound 3b (McN-5652-Z) was found to possess exceptional activity in these assays, and the activity was attributable almost exclusively to the (+)-6S,10bR enantiomer. Ten closely related analogues were synthesized, tested, and compared among themselves and with some previously prepared compounds, both in vivo and in vitro. Several trans diastereomers exhibited strong inhibition of 5-HT uptake and substantial potentiation of 5-HT, while the cis diastereomers (3a, 4a, and 10a) tested were virtually devoid of such activity. Although 3b was only moderately selective in inhibiting the uptake of 5-HT vs NE, its 10-substituted analogues 4b, 7b-9b had improved 5-HT selectivity relative to NE, to the extent of 20-25 times (150-200 times relative to DA). Of these more selective compounds (in vitro), only 4b and 7b had substantial activity in vivo. Sulfoxide 11b appeared to function as a prodrug of 3b in vivo.

  DOI：

  10.1021/jm00172a018

文献信息

• [EN] TACHYKININ RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR TACHYKININE
  申请人：LILLY CO ELI

  公开号：WO2005000821A1

  公开（公告）日：2005-01-06

  The present invention relates to selective NK-1 receptor antagonists of Formula (I) or a pharmaceutically acceptable salt thereof, for the treatment of disorders associated with an excess of tachykinins.

  本发明涉及选择性NK-1受体拮抗剂的化学式(I)或其药用盐，用于治疗与过多的缓激肽相关的疾病。
• Zinc‐Catalyzed Asymmetric Hydrosilylation of Cyclic Imines: Synthesis of Chiral 2‐Aryl‐Substituted Pyrrolidines as Pharmaceutical Building Blocks
  作者：Izabela Węglarz、Karol Michalak、Jacek Mlynarski

  DOI：10.1002/adsc.202001043

  日期：2021.3.2

  cyclic imines promoted by a chiral zinc complex is reported. In situ generated zinc‐ProPhenol complex with silane afforded pharmaceutically relevant enantioenriched 2‐aryl‐substituted pyrrolidines in high yields and with excellent enantioselectivities (up to 99% ee). The synthetic utility of presented methodology is demonstrated in an efficient synthesis of the corresponding chiral cyclic amines, being pharmaceutical

  据报道，由手性锌配合物促进的环状亚胺的首次成功的对映选择性氢化硅烷化。原位生成的锌-苯酚锌与硅烷的络合物以高收率和优异的对映选择性（高达99％ee）提供了药学上对映体富集的对映体富集的2-芳基取代的吡咯烷。所提出方法的合成效用在相应手性环胺的有效合成中得到证明，所述手性环胺是阿替卡普特和拉罗替尼的药物前体。
• Nickel-Catalyzed Annulations of <i>ortho</i>-Haloarylimines
  作者：Srinivas Kolluru、Manvendra Singh、Bryce Gaskins、Zarko Boskovic

  DOI：10.1021/acscatal.1c03092

  日期：2021.8.20

  adjacent anti stereocenters and a free secondary amine. Spirocycles are formed from cyclic imines. We characterized the key oxidative addition intermediate and identified a major path leading to competing homocoupling products. The activation energy of oxidative addition and the rate of oxidative addition complex isomerization were determined. The sensitivity of the reaction to reaction conditions was established

  我们报告了邻卤代芳基亚胺和贫电子烯烃之间的镍催化环化反应的发现、发展和机理。该反应产生两个相邻的反立体中心和一个游离的仲胺。螺环由环状亚胺形成。我们表征了关键的氧化加成中间体，并确定了导致竞争同源偶联产物的主要途径。测定了氧化加成的活化能和氧化加成络合物异构化的速率。以定量方式建立反应对反应条件的敏感性，并介绍了该方法的范围和局限性。
• Tachykinin receptor antagonists
  申请人：Amegadzie Kudzovi Albert

  公开号：US20060160794A1

  公开（公告）日：2006-07-20

  The present invention relates to selective NK-1 receptor antagonists of Formula (I) or a pharmaceutically acceptable salt thereof, for the treatment of disorders associated with an excess of tachykinins.

  本发明涉及公式(I)或其药学上可接受的盐的选择性NK-1受体拮抗剂，用于治疗与过量Tachykinins相关的疾病。
• MARYANOFF, BRUCE E.;VAUGHT, JEFFRY L.;SHANK, RICHARD P.;MECOMSEY, DAVID F+, J. MED. CHEM., 33,(1990) N0, C. 2793-2797
  作者：MARYANOFF, BRUCE E.、VAUGHT, JEFFRY L.、SHANK, RICHARD P.、MECOMSEY, DAVID F+

  DOI：——

  日期：——