(-)-quinine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (-)-quinine
• 英文别名: (R)-[(2S,4S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: LOUPRKONTZGTKE-MYUJHIMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-二溴-2-丁烯 、 (-)-quinine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以63%的产率得到(1R,7R,10S,E)-1-(6-methoxyquinolin-4-yl)-9-vinyl-1,3,6,8,9,10,11,11a-octahydro-7,10-ethanopyrido[2,1-c][1,4]oxazocin-7-ium bromide
  参考文献：
  名称：

  新型手性相转移催化剂催化甘氨酸衍生物的不对称烷基化反应

  摘要：

  本文合成了一系列从金鸡纳生物碱衍生的手性相转移催化剂，并将其用于甘氨酸衍生物的不对称烷基化反应，具有高收率和中等至优异的ee值（39.5–99.7％）。

  DOI：

  10.1016/j.tetlet.2015.01.063
• 作为产物：
  描述：

  在 氧气 、 sodium hydride 作用下， 以 水 为溶剂， 生成 (-)-quinine
  参考文献：
  名称：

  Unification of Reaction Metrics for Green Chemistry:  Applications to Reaction Analysis

  摘要：

  A formalism is presented which unifies key reaction metrics associated with "greenness" in chemical reactions with respect to raw materials usage. The fundamental basis of this treatment begins with balanced chemical reactions in which byproducts are identified. The primary or kernel metrics are reaction yield, scale of reaction, stoichiometric factor (SF), and Trost's atom economy (AE). The stoichiometric factor is a new metric that is defined to account for reactions run under nonstoichiometric conditions, that is, with one or more reagents in excess. A general relation for reaction mass efficiency (RME) is derived which shows that this metric is a composite of the aforementioned primary metrics and takes into account solvent usage in the reaction and postreaction phases (workup and purification). The Sheldon environmental impact factor E is treated at various levels of complexity according to what is constituted as waste and is shown to be related to RME by a simple inverse expression. A flowchart is presented which shows other simple relationships connecting all metrics. Raw material costs, optimum conditions for recycling or reclaiming catalysts and reaction and postreaction solvents, and the handling of reactions giving isomeric products are also assessed. General algorithms are proposed for determining kernel reaction metrics for linear and convergent sequences that can be used to compare the intrinsic, or best-case scenario, green performances of synthetic plans to a common target structure. All key relationships can be implemented in a spreadsheet format from which reaction histograms or "maps" can be generated. Individual reaction RME performances can be gauged, ranked, and decomposed according to AE, SF, and reaction yield kernel metrics. This allows for the easy identification of best and worst reactions in a process or sequence. Example applications of the present methodology include the following: (a) a comparative analysis of the synthesis of quinine by the classic Woodward-Rabe and the modern greener Stork methods; (b) the analysis of the industrial synthesis of sildenafil (Viagra) by a convergent strategy; and (c) the analysis of kinetic resolution of racemic alcohols by a successive oxidation and recycling reduction cycle.

  DOI：

  10.1021/op049803n
• 作为试剂：
  描述：

  甲醇 、 (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 在 (-)-quinine 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 16.0h， 以99%的产率得到bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monomethyl ester
  参考文献：
  名称：

  [EN] A METHOD OF INHIBITING HEPATITIS C VIRUS BY COMBINATION OF A 5,6-DIHYDRO-1H-PYRIDIN-2-ONE AND ONE OR MORE ADDITIONAL ANTIVIRAL COMPOUNDS
  [FR] PROCÉDÉ D'INHIBITION DU VIRUS DE L'HÉPATITE C PAR COMBINAISON D'UNE 5,6-DIHYDRO-1H-PYRIDIN-2-ONE ET D'UN OU PLUSIEURS COMPOSÉS ANTIVIRAUX SUPPLÉMENTAIRES

  摘要：

  本发明涉及一种治疗乙型肝炎病毒感染的方法，通过给予N-{3-[(1R,2S,7R,8S)-3-(4-氟苯基)-6-羟基-4-氧代-3-氮杂三环[6.2.1.02,7]十一碳-5-烯-5-基]-1,1-二氧代-1,4-二氢-1λ6-苯并[1,2,4]噻二唑-7-基}-甲磺酰胺以及一个或多个附加的抗病毒化合物或含有此类化合物的药物组合物。

  公开号：

  WO2010042834A1

文献信息

• PROCESS FOR PREPARING DIASTEREOMERICALLY ENRICHED PHOSPHORAMIDATE DERIVATIVES OF NUCLEOSIDE COMPOUNDS FOR TREATMENT OF VIRAL INFECTIONS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20150183818A1

  公开（公告）日：2015-07-02

  The present invention is directed to a process for preparing diastereomerically enriched nucleoside phosphoramidates having the formula I:

  本发明涉及一种制备式I的对映体富集核苷酸磷酰胺酯的方法：
• METHODS OF PREPARING 1H-PYRROLO[2,3-B]PYRIDINE DERIVATES
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：EP3851437A2

  公开（公告）日：2021-07-21

  A method of preparing compound (N):

  一种制备化合物（N）的方法：
• METHODS OF PREPARING INHIBITORS OF INFLUENZA VIRUSES REPLICATION
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：EP3068782B1

  公开（公告）日：2018-05-23
• PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE ISOXAZOLINE COMPOUNDS
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：US20170217953A1

  公开（公告）日：2017-08-03

  The present invention relates to a process for the preparation of a compound of formula (I) wherein A 1 and A 2 are C—H, or one of A 1 and A 2 is C—H and the other is N; R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl; each R 2 is independently bromo, chloro, fluoro or trifluoromethyl; R 3 is hydrogen; R 4 is hydrogen, halogen, methyl, halomethyl or cyano; or R 3 and R 4 together form a bridging 1,3-butadiene group; R 5 is chlorodifluoro-methyl or trifluoromethyl; n is 2 or 3; by reacting a compound of formula (II) wherein A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 and n is as defined under formula (I) above, with hydroxylamine, a base and a chiral catalyst, characterized in that the chiral catalyst is a dimeric chiral catalyst of formula (III) wherein R 6 , R 7 , R 8 , R 9 , R 10 and X are as defmed in claim 1 .
• US9815829B2
  申请人：——

  公开号：US9815829B2

  公开（公告）日：2017-11-14