(1R,2S)-2-(benzyloxy)cyclohexanamine | 1166399-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-2-(benzyloxy)cyclohexanamine
• 英文别名: (1R,2S)-2-phenylmethoxycyclohexan-1-amine
• CAS: 1166399-02-5
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: NTHNRYLIXJZHRZ-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(benzyloxy)cyclohexanamine 、 3-(octylamino)-3-oxopropanoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Immunosuppressive but Non-LasR-Inducing Analogues of the Pseudomonas aeruginosa Quorum-Sensing Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone

  摘要：

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.

  DOI：

  10.1021/jm2001019
• 作为产物：
  描述：

  N-((1R,2S)-2-Benzyloxy-cyclohexyl)-acetamide 在 氢氧化钾 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 20.0h， 以76%的产率得到(1R,2S)-2-(benzyloxy)cyclohexanamine
  参考文献：
  名称：

  2-氧代喹啉衍生物作为血小板聚集抑制剂的研究，IV。6- [4-（1-（1-环己基-1H-5-四唑基）丁氧基] -2-氧-1,2,3,4-四氢喹啉（OPC-13013）的代谢物的合成及生物活性。

  摘要：

  6-[4-(1-环己基-1H-5-四唑基)丁氧基]-2-氧代-1,2,3,4-四氢喹啉（OPC-13013）（1）的代谢产物，该化合物具有强效的血小板聚集抑制活性和脑部血管舒张活性，被合成以确认其结构并检测其抑制活性。通过与合成化合物进行比较，明确鉴定出四种主要代谢产物（2a-c和3）和一个仅在人体中发现的具体代谢产物（4）的结构。3,4-去氢-OPC-13013（3）的抑制活性约为1的三倍，而两种代谢产物（2a和2c）的活性与1几乎相等。

  DOI：

  10.1248/cpb.33.1140

文献信息

• METHOD FOR ONE-POT PRODUCTION OF A PRIMARY AMINE FROM AN ALCOHOL
  申请人：EntreChem, S.L.

  公开号：EP3415630A1

  公开（公告）日：2018-12-19

  A method for producing a compound of formula (III) or a salt thereof, wherein said process comprises the following steps: (a) forming a mixture comprising a compound of formula (II) by adding an organocatalyst to a compound of formula (I) in an aqueous medium comprising an oxidizing agent and an organic co-solvent; and (b) adding an aqueous buffer, a transamination catalyst, an amine donor compound and a cofactor to the mixture obtained in step (a), wherein said transamination catalyst is added at the same time as or after adding said aqueous buffer.

  一种生产式（III）化合物的方法 或其盐的方法，其中所述工艺包括以下步骤： (a) 形成包含式（II）化合物的混合物 将有机催化剂加入到式（I）化合物中 在包含氧化剂和有机助溶剂的水介质中；以及 (b) 向步骤(a)中得到的混合物中加入水性缓冲剂、转胺催化剂、胺供体化合物和辅助因子，其中所述转胺催化剂是在加入所述水性缓冲剂的同时或之后加入的。
• Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: A novel class of anticancer agents
  作者：S.N. Manjula、N. Malleshappa Noolvi、K. Vipan Parihar、S.A. Manohara Reddy、Vijay Ramani、Andanappa K. Gadad、Gurdial Singh、N. Gopalan Kutty、C. Mallikarjuna Rao

  DOI：10.1016/j.ejmech.2008.12.002

  日期：2009.7

  A novel series of optically active 2-aminobenzothiazole derivatives were synthesized by reaction of optically active amine (1) with thiophosgene to obtain optically active isothiocyanates (IIa-h) which on condensation with 4-fluoro-3-chloro aniline (III) yielded various optically active thioureas (IVa-h). Further oxidative cyclisation in the presence of bromine and chloroform yielded title compounds (Va-h). The structures of these compounds were established by IR, H-1 NMR, C-13 NMR, Mass and HRMS. The compounds (IVA-h and Va-h) were evaluated for in vitro cytotoxicity against mouse Ehrlich Ascites Carcinoma (EAC) and two human cancer cell lines (MCF-7 and HeLa). In preliminary MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] cytotoxicity studies the optically active thiourea derivatives (IVe, IVf and IVh) were found most effective. In EAC cells the IC50 values for IVe, IVf, IVh and Vg were found in the range of 10-24 mu M, whereas in MCF-7 and HeLa cells the IC50 values were observed in the range of 15-30 mu M and 33-48 mu M, respectively. In alkaline comet assay the compounds (We and IVf) showed dose-dependent DNA damaging activity. (C) 2008 Elsevier Masson SAS. All rights reserved.
• VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEM 2-BENZYLOXYCYCLOHEXYLAMIN
  申请人：BASF SE

  公开号：EP2069517A1

  公开（公告）日：2009-06-17
• METHOD FOR PRODUCING OPTICALLY ACTIVE 2-BENZYLOXYCYCLOHEXYLAMINE
  申请人：Ditrich Klaus

  公开号：US20090280544A1

  公开（公告）日：2009-11-12

  The present invention relates to a method for the enantioselective acylation of trans-2-benzyloxycyclohexylamine or cis-2-benzyloxycyclohexylamine, according to which an enantiomer mixture of 2-benzyloxycyclohexylamine is reacted with an acylation agent in the presence of a hydrolase. The invention also relates to a method for producing optically active trans-stereoisomers of 2-benzyloxycyclohexylamine.
• [DE] VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEM 2-BENZYLOXYCYCLOHEXYLAMIN<br/>[EN] METHOD FOR PRODUCING OPTICALLY ACTIVE 2-BENZYLOXYCYCLOHEXYLAMINE<br/>[FR] PROCÉDÉ POUR LA PRODUCTION DE 2-BENZYLOXYCYCLOHEXYLAMINE OPTIQUEMENT ACTIVE
  申请人：BASF AG

  公开号：WO2008031852A1

  公开（公告）日：2008-03-20

  [EN] The invention relates to a method for the enantioselective acylation of trans-2-benzyloxycyclohexylamine or cis-2-benzyloxycyclohexylamine, according to which an enantiomer mixture of 2-benzyloxycyclohexylamine is reacted with an acylation agent in the presence of a hydrolase. The invention also relates to a method for producing optically active trans-stereoisomers of 2-benzyloxycyclohexylamine.
  [FR] L'invention concerne un procédé pour l'acylation énantiosélective de 2-benzyloxycyclohexylamine cis ou trans, selon lequel on fait réagir un mélange d'énantiomères de la 2-benzyloxycyclohexylamine avec un agent d'acylation en présence d'une hydrolase. L'invention concerne également un procédé pour la production de stéréoisomères trans optiquement actifs de la 2-benzyloxycyclohexylamine.
  [DE] Die vorliegende Erfindung betrifft ein Verfahren zur enantioselektiven Acylierung von trans- oder cis-2-Benzyloxycyclohexylamin, bei dem man ein Enantiomerengemisch des 2-Benzyloxycyclohexylamins mit einem Acylierungsmittel in Gegenwart einer Hydrolase umsetzt, sowie ein Verfahren zur Herstellung optisch aktiver trans- Stereoisomere von 2-Benzyloxycyclohexylamin.