(1R,2R)-2-(环丙基氨基)环己烷-1-醇 | 189362-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2R)-2-(环丙基氨基)环己烷-1-醇
• 中文别名: (1R,2R)-2-环丙胺基环己醇；(1R,2R)-2-环丙烷基环己醇
• 英文名称: (1R,2R)-2-(cyclopropylamino)cyclohexan-1-ol
• CAS: 189362-43-4
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: CFEAMNVUJMQGNK-RKDXNWHRSA-N

物化性质

• 沸点：
  261.8±33.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-[3-(1-imidazolyl)carbonylaminopropoxy]carbostyril 、 (1R,2R)-2-(环丙基氨基)环己烷-1-醇 以 氯仿 为溶剂， 以63%的产率得到1-环丙基-1-[(1R,2R)-2-羟基环己基]-3-[3-[(2-氧代-1H-喹啉-6-基)氧基]丙基]脲
  参考文献：
  名称：

  2(1H)-Quinolinone derivatives as novel anti-arteriostenotic agents showing anti-thrombotic and anti-hyperplastic activities

  摘要：

  In order to search for anti-arteriostenotic agents, a series of 2(1H)-quinolinone derivatives was synthesized and evaluated for anti-thrombotic activity and for anti-hyperplastic activity. From this series, (-)-6-[3-[3-cyclopropyl-3-[(1R,2R)-2-hydroxycyclohexyl]ureido] propoxy]-2(1H)-quinolinone (1p, OPC-33509) was selected as the best candidate by balancing the efficacy on anti-thrombosis and anti-hyperplasia. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00246-7
• 作为产物：
  描述：

  (1R,2R)-2-(cyclopropylamino)cyclohexyl (S)-2-hydroxy-2-phenylacetate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以100%的产率得到(1R,2R)-2-(环丙基氨基)环己烷-1-醇
  参考文献：
  名称：

  2(1H)-Quinolinone derivatives as novel anti-arteriostenotic agents showing anti-thrombotic and anti-hyperplastic activities

  摘要：

  In order to search for anti-arteriostenotic agents, a series of 2(1H)-quinolinone derivatives was synthesized and evaluated for anti-thrombotic activity and for anti-hyperplastic activity. From this series, (-)-6-[3-[3-cyclopropyl-3-[(1R,2R)-2-hydroxycyclohexyl]ureido] propoxy]-2(1H)-quinolinone (1p, OPC-33509) was selected as the best candidate by balancing the efficacy on anti-thrombosis and anti-hyperplasia. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00246-7
• 作为试剂：
  描述：

  6-[3-(1-imidazolyl)carbonylaminopropoxy]carbostyril 、 (1R,2R)-2-(环丙基氨基)环己烷-1-醇 在 (1R,2R)-2-(环丙基氨基)环己烷-1-醇 作用下， 以63的产率得到1-环丙基-1-[(1R,2R)-2-羟基环己基]-3-[3-[(2-氧代-1H-喹啉-6-基)氧基]丙基]脲
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 1998, 8, 1471-1476

  摘要：

  DOI：

文献信息

• Asymmetric Amination of meso-Epoxide with Vegetable Powder as a Low-Toxicity Catalyst
  作者：Yuki Takeuchi、Tatsuhiro Asano、Kazuya Tsuzaki、Koichi Wada、Hiroyuki Kurata

  DOI：10.3390/molecules25143197

  日期：——

  This paper describes the scope and limitation of substrates subjected to asymmetric amination with epoxides catalyzed by a soluble soybean polysaccharide (Soyafibe S-DN), which we recently discovered from the reaction of 1,2-epoxycyclohexane with cyclopropylamine. Various meso-epoxides reacted with various amines afforded the corresponding products with good enantiomeric selectivity. Since it was found that pectin was found to have a catalytic ability after screening commercially available polysaccharides, we studied 33 different vegetable powders having pectic substances, and we found that many vegetable powders showed catalytic ability. These results should guide in using vegetable components as low-toxic catalysts for the production of pharmaceuticals.

  本文描述了由可溶性大豆多糖（Soyafibe S-DN）催化的环氧化合物与环丙胺不对称胺化反应所受限的基质范围和限制性。我们最近从1,2-环氧环己烷与环丙胺反应中发现了这种多糖。各种中间体环氧化合物与各种胺反应产生了相应的产物，具有良好的对映选择性。在筛选商业可获得的多糖后发现果胶具有催化能力后，我们研究了33种含有果胶物质的不同蔬菜粉末，发现许多蔬菜粉末显示出催化能力。这些结果应该指导在制药生产中使用蔬菜成分作为低毒性催化剂。
• Carbostyril derivatives
  申请人：D. Western Therapeutics Institiute

  公开号：US06143763A1

  公开（公告）日：2000-11-07

  A carbostyril derivative of the formula (1): ##STR1## wherein A is lower alkylene, R is H, halogen or lower alkoxy, R.sup.1 and R.sup.2 are each lower alkyl being optionally substituted by OH, lower alkoxy, phenyl-lower alkoxy or lower alkanoyloxy; cycloalkyl being optionally substituted by OH, hydroxy-lower alkoxy or lower alkanoyloxy; or amino being optionally substituted by lower alkyl or cycloalkyl, R.sup.3 is H, lower alkyl, lower alkenyl or hydroxy-lower alkyl, and the bond between 3- and 4-positions of the carbostyril nucleus is single or double, provided that when R and R.sup.3 are H, R.sup.1 and R.sup.2 should not be either unsubstituted lower alkyl or unsubstituted cycloalkyl, or a salt thereof, which shows antithrombotic activities, intima thickening inhibitory activity, the platelet mass dissociating activity and increasing activity of the blood flow in the brain and the peripheral vessel, and hence, is useful as medicines in the prophylaxis or treatment of various ischemic diseases.

  公式(1)的卡博斯蒂烯衍生物：##STR1## 其中A是较低的烷基，R是H，卤素或较低的烷氧基，R.sup.1和R.sup.2都是较低的烷基，可以选择性地被OH，较低的烷氧基，苯基-较低的烷氧基或较低的烷酰氧基替换；环烷基可以选择性地被OH，羟基-较低的烷氧基或较低的烷酰氧基替换；或氨基可以选择性地被较低的烷基或环烷基替换，R.sup.3是H，较低的烷基，较低的烯基或羟基-较低的烷基，且卡博斯蒂烯核的3-和4-位之间的键是单键或双键，但是当R和R.sup.3为H时，R.sup.1和R.sup.2不应是未取代的较低烷基或未取代的环烷基，或其盐，该衍生物表现出抗血栓活性、内膜增厚抑制活性、血小板质量解离活性和增加脑血流和外周血管的活性，因此，可用作预防或治疗各种缺血性疾病的药物。
• Catalytic Asymmetric Amination of <i>meso</i>-Epoxide Using Soy Polysaccharide (Soyafibe S-DN)
  作者：Yuki Takeuchi、Tatsuhiro Asano、Kazuya Tsuzaki、Koichi Wada

  DOI：10.1246/bcsj.20170369

  日期：2018.4.15

  The asymmetric amination of epoxides is an effective method to synthesize chiral β-aminoalcohols and their components as pharmaceuticals. We have developed a new catalyst system for the asymmetric amination of 1,2-epoxycyclohexane with cyclopropylamine. We have also found that water-soluble soy polysaccharide (Soyafibe S-DN) functions as a catalyst. This catalytic reaction proceeded under mild conditions

  环氧化物的不对称胺化是合成手性β-氨基醇及其组分作为药物的有效方法。我们开发了一种新的催化剂体系，用于 1,2-环氧环己烷与环丙胺的不对称胺化。我们还发现水溶性大豆多糖 (Soyafibe S-DN) 起到催化剂的作用。该催化反应在 37-40°C 的含水甲苯中在温和条件下进行。(1R,2R)-2-(环丙氨基)环己-1-醇通过使用该催化剂体系将1,2-环氧环己烷与环丙胺不对称胺化而以64%对映体过量(ee)获得；它还通过纯化以富马酸盐的形式以 >99% 的 ee 制得。这种可溶性大豆多糖的催化活性保持不变，即使用蛋白酶处理，但是当用糖链降解酶处理时它的活性消失了。这些结果表明多糖而不是蛋白质作为该反应的催化剂。于是，我们发现...
• [EN] CARBOSTYRIL DERIVATIVES AS ANTITHROMBOTIC AGENTS<br/>[FR] DERIVES DE CARBOSTYRYLE EN TANT QU'AGENTS ANTITHROMBOTIQUES
  申请人：OTSUKA PHARMACEUTICAL COMPANY, LIMITED

  公开号：WO1997012869A1

  公开（公告）日：1997-04-10

  (EN) A carbostyril derivative of formula (1), wherein A is lower alkylene, R is H, halogen or lower alkoxy, R1 and R2 are each lower alkyl being optionally substituted by OH, lower alkoxy, phenyl-lower alkoxy or lower alkanoyloxy; cycloalkyl being optionally substituted by OH, hydroxy-lower alkoxy or lower alkanoyloxy; or amino being optionally substituted by lower alkyl or cycloalkyl, R3 is H, lower alkyl, lower alkenyl or hydroxy-lower alkyl, and the bond between 3- and 4-positions of the carbostyril nucleus is single or double, provided that when R and R3 are H, R1 and R2 should not be either unsubstituted lower alkyl or unsubstituted cycloalkyl, or a salt thereof, which shows antithrombotic activities, intima thickening inhibitory activity, the platelet mass dissociating activity and increasing activity of the blood flow in the brain and the peripheral vessel, and hence, is useful as medicines in the prophylaxis or treatment of various ischemic diseases.(FR) La présente invention concerne un dérivé de carbostyryle de formule (1), dans laquelle A est un alkylène inférieur, R est H, halogène ou un alcoxy inférieur, R1 et R2 sont chacun un alkyle inférieur, éventuellement substitué par OH, un alcoxy inférieur, un phényle-alcoxy inférieur ou un alcanoyloxy inférieur; le cycloalkyle est facultativement substitué par OH, un hydroxy-alcoxy inférieur ou un alcanoyloxy inférieur; ou l'amino est facultativement substitué par un alkyle inférieur ou un cycloalkyle; R3 est H, un alkyle inférieur, un alkényle inférieur ou un hydroxy-alkyle inférieur, et la liaison entre les positions 3 et 4 du noyau de carbostyryle est simple ou double, à condition que, quand R et R3 sont H, R1 et R2 ne soient pas soit un alkyle inférieur non substitué, soit un cycloalkyle non substitué ou un sel d'un de ces composés. Le dérivé selon l'invention manifeste des propriétés antithrombotiques, inhibitrices de l'épaississement de l'intima, de dissociation des amas de plaquettes et d'accroissement du débit sanguin dans le cerveau et dans les vaisseaux périphériques. Par conséquent, il est utile comme médicament dans la prophylaxie ou le traitement de diverses affections ischémiques.

  本发明涉及一种式样为(1)式、具有取代基如下所述的碳扼基衍生物，其中A为下端烷二元基，R为氢、卤素或下端烷氧基，R1和R2均为下端烷基和选代羟基、下端烷氧基、苯-烷氧基或烷基酰氧基；6-环烷基可选地被羟基、羟基-烷氧基或烷基酰氧基取代；氨基可选地被下端烷基或环烷基取代，R3为氢、下端烷基、烯基或羟基-烷基，且碳扼基核中3-位和4-位的键为单键或双键，其条件是：当R和R3为氢时，R1和R2不应分别为未取代的下端烷基或未取代的环烷基，或分别为它们的盐，该衍生物具有抗血小板凝聚作用、抑制内膜增厚作用、防止血小板膜离解作用，以及增加脑部和周围血管血液流量的作用。因此，该衍生物可用于预防或治疗各种缺血性疾病。
• CARBOSTYRIL DERIVATIVES AS ANTITHROMBOTIC AGENTS
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0796248A1

  公开（公告）日：1997-09-24