(3-chloropropylidene)cyclohexane | 18022-81-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: (3-chloropropylidene)cyclohexane
• 英文别名: 3-Chloropropylidenecyclohexane
• CAS: 18022-81-6
• 化学式: C₉H₁₅Cl
• mdl: MFCD19233581
• 分子量: 158.671
• InChiKey: UPNYXTBCFWEXMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6,7-二甲氧基-1,2,3,4-四氢异喹啉 、 (3-chloropropylidene)cyclohexane 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以17%的产率得到2-(3-cyclohexylidenepropyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline
  参考文献：
  名称：

  Small P-gp modulating molecules: SAR studies on tetrahydroisoquinoline derivatives

  摘要：

  The development of small molecules as P-gp modulating agents and SAR studies on these ligands represented the aim of the present work. A series of 6,7-dimethoxytetrahydroisoquinoline derivatives was prepared and their ability to inhibit P-gp activity has been evaluated. The basic nucleus of these compounds, common to the best P-gp inhibitors such as Tariquidar and Elacridar, has been functionalized with no-basic moiety from our studied sigma receptor ligands displaying potent P-gp inhibition. The best results were obtained for compounds 3c and 3a (EC50 = 1.64 and 4.86 mu M, respectively) and these results were remarkable because Elacridar showed in the same biological evaluation similar inhibitory activity (EC50 = 2 mu M). SAR studies displayed that the removal of double bond on the spacer or its shifting into tetraline ring decreased the P-gp inhibiting activity. Moreover, the P-gp inhibition mechanism of tested compounds was investigated by three selected biological experiments. The results displayed that only compound 3c was P-gp inhibitor as Elacridar, while compound 3a and reference compounds Cyclosporin A and Verapamil modulated P-gp activity saturating the efflux pump as substrates. Flow cytometry studies carried out in Doxorubicin resistant breast cancer cell line (MCF7/Adr) confirmed that compound 3c increased Doxorubicin cell accumulation 5.7-fold. In addition, in MCF7/ Adr, antiproliferative effect of 5 mu M Doxorubicin shifted from 5% to 95% when co-administered with compound 3c (20 mu M). The present study suggested a new class of small molecules displaying P-gp inhibitor activity differing from reference compounds Elacridar and Tariquidar for a simplified, and in the meantime, efficacious no-basic moiety. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.039
• 作为产物：
  描述：

  环亚丙基环己烷 在 potassium chloride 、 水 作用下， 以 二氧化硫 为溶剂， 60.0 ℃ 、810.65 kPa 条件下， 反应 1.0h， 以19%的产率得到(3-chloropropylidene)cyclohexane
  参考文献：
  名称：

  液态二氧化硫中亚甲基环丙烷与卤化物的开环

  摘要：

  亚甲基环丙烷（MCP）与第一和第二族金属卤化物和卤化铵在液体SO 2中进行开环反应，得到均烯丙基卤化物，它们是有机合成中的通用试剂。所开发的反应条件与酸不稳定的底物如N -Boc保护的化合物相容。液体SO 2是具有路易斯酸性质的极性反应介质，可溶解无机盐。通过对照实验证明了SO 2的独特性质：1）在常规溶剂中与上述盐进行反应后，在催化量的H 3 PO 4（相似的pK）存在下也未观察到MCP开环a等于H 2 SO 3），或不存在H 3 PO 4；2）SO 2在THF中的溶液表现出与液体SO 2相似的性质。

  DOI：

  10.1016/j.tetlet.2020.152528

文献信息

• ISAEV O. I., AZERB. XIM. ZH.,(1986) N 5, 53-56
  作者：ISAEV O. I.

  DOI：——

  日期：——
• Ring opening of methylenecyclopropanes with halides in liquid sulfur dioxide
  作者：Kristaps Leškovskis、Krista Gulbe、Anatoly Mishnev、Māris Turks

  DOI：10.1016/j.tetlet.2020.152528

  日期：2020.11

  Methylenecyclopropanes (MCP) undergo ring opening reactions with group I and II metal halides and ammonium halides in liquid SO2 to afford homoallylic halides, which are versatile reagents in organic synthesis. The developed reaction conditions are compatible with acid-labile substrates such as N-Boc-protected compounds. Liquid SO2 is a polar reaction medium with Lewis acid properties that solubilizes

  亚甲基环丙烷（MCP）与第一和第二族金属卤化物和卤化铵在液体SO 2中进行开环反应，得到均烯丙基卤化物，它们是有机合成中的通用试剂。所开发的反应条件与酸不稳定的底物如N -Boc保护的化合物相容。液体SO 2是具有路易斯酸性质的极性反应介质，可溶解无机盐。通过对照实验证明了SO 2的独特性质：1）在常规溶剂中与上述盐进行反应后，在催化量的H 3 PO 4（相似的pK）存在下也未观察到MCP开环a等于H 2 SO 3），或不存在H 3 PO 4；2）SO 2在THF中的溶液表现出与液体SO 2相似的性质。
• Small P-gp modulating molecules: SAR studies on tetrahydroisoquinoline derivatives
  作者：Nicola Antonio Colabufo、Francesco Berardi、Mariangela Cantore、Maria Grazia Perrone、Marialessandra Contino、Carmela Inglese、Mauro Niso、Roberto Perrone、Amalia Azzariti、Grazia Maria Simone、Letizia Porcelli、Angelo Paradiso

  DOI：10.1016/j.bmc.2007.09.039

  日期：2008.1

  The development of small molecules as P-gp modulating agents and SAR studies on these ligands represented the aim of the present work. A series of 6,7-dimethoxytetrahydroisoquinoline derivatives was prepared and their ability to inhibit P-gp activity has been evaluated. The basic nucleus of these compounds, common to the best P-gp inhibitors such as Tariquidar and Elacridar, has been functionalized with no-basic moiety from our studied sigma receptor ligands displaying potent P-gp inhibition. The best results were obtained for compounds 3c and 3a (EC50 = 1.64 and 4.86 mu M, respectively) and these results were remarkable because Elacridar showed in the same biological evaluation similar inhibitory activity (EC50 = 2 mu M). SAR studies displayed that the removal of double bond on the spacer or its shifting into tetraline ring decreased the P-gp inhibiting activity. Moreover, the P-gp inhibition mechanism of tested compounds was investigated by three selected biological experiments. The results displayed that only compound 3c was P-gp inhibitor as Elacridar, while compound 3a and reference compounds Cyclosporin A and Verapamil modulated P-gp activity saturating the efflux pump as substrates. Flow cytometry studies carried out in Doxorubicin resistant breast cancer cell line (MCF7/Adr) confirmed that compound 3c increased Doxorubicin cell accumulation 5.7-fold. In addition, in MCF7/ Adr, antiproliferative effect of 5 mu M Doxorubicin shifted from 5% to 95% when co-administered with compound 3c (20 mu M). The present study suggested a new class of small molecules displaying P-gp inhibitor activity differing from reference compounds Elacridar and Tariquidar for a simplified, and in the meantime, efficacious no-basic moiety. (c) 2007 Elsevier Ltd. All rights reserved.