(R)-伪可卡因 | 50-36-2

• 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: (R)-伪可卡因
• 中文别名: 2-甲基庚酰胺
• 英文名称: (+/-)-pseudococaine
• 英文别名: (+/-)-Pseudococain；Pseudococaine；methyl (1R,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 50-36-2；478-73-9；518-97-8；668-19-9；7058-74-4；21030-42-2；21030-43-3；21030-44-4；21206-60-0；47195-07-3；85354-45-6；131722-66-2；131829-33-9
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: ZPUCINDJVBIVPJ-XGUBFFRZSA-N

物化性质

• 熔点：
  47°
• 比旋光度：
  D20 +42° (c = 5 in chloroform)
• 沸点：
  395.2±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 碰撞截面：
  169.74 Ų [M+H]+

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 安全说明：
  S26,S36/37,S36/37/39,S45
• 危险类别码：
  R23/24/25,R43
• WGK Germany：
  3
• RTECS号：
  YM2800000
• 包装等级：
  II
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 1648 3/PG 2

反应信息

• 作为反应物：
  描述：

  (R)-伪可卡因 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以100%的产率得到Pseudococaine hydrochloride
  参考文献：
  名称：

  Asymmetric Synthesis of the Tropane Alkaloid (+)-Pseudococaine via Ring-Closing Iodoamination

  摘要：

  Ring-closing iodoamination of terf-butyl 2-hydroxy-7[N-methyl-N-(alpha-methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane scaffolds in >99:1 dr. Subsequent elaboration of one of these templates provided access to (+)-pseudococaine hydrochloride, in seven steps and 31% overall yield from commercially available starting materials.

  DOI：

  10.1021/ol3020607
• 作为产物：
  描述：

  tert-butyl (1R,2S,3R,4R,5S)-3-hydroxy-4-iodo-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 在 4-二甲氨基吡啶 、 氯化亚砜 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 (R)-伪可卡因
  参考文献：
  名称：

  Asymmetric Synthesis of the Tropane Alkaloid (+)-Pseudococaine via Ring-Closing Iodoamination

  摘要：

  Ring-closing iodoamination of terf-butyl 2-hydroxy-7[N-methyl-N-(alpha-methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane scaffolds in >99:1 dr. Subsequent elaboration of one of these templates provided access to (+)-pseudococaine hydrochloride, in seven steps and 31% overall yield from commercially available starting materials.

  DOI：

  10.1021/ol3020607

文献信息

• MOLECULES THAT STIMULATE THE IMMUNE SYSTEM FOR TREATMENT OF DRUG ADDICTION, METHODS OF SYNTHESIS, ANTIDRUG VACCINE AND USES
  申请人：UNIVERSIDADE FEDERAL DE MINAS GERAIS

  公开号：US20200385376A1

  公开（公告）日：2020-12-10

  This technology relates to immune system stimulating molecules to be used in the treatment of drug addiction and abuse and their synthesis processes. These molecules have a calixarene chemical structure, preferably calix[4]arene and/or calix[8]arene, coupled to an hapten analogous to cocaine, preferably GNE and/or GNC. An anti-drug vaccine, specifically anti-cocaine, is also described using such molecules. The anti-drug vaccine can be also used to prevent fetal exposure to drugs in pregnant women who use drugs and do not wish or cannot stop their use during pregnancy.

  这项技术涉及用于治疗药物成瘾和滥用的免疫系统刺激分子及其合成过程。这些分子具有杯芳烃化学结构，最好是杯[4]芳烃和/或杯[8]芳烃，与类似于可卡因的半抗原偶联，最好是GNE和/或GNC。还描述了使用这种分子的抗药疫苗，特别是抗可卡因。这种抗药疫苗还可用于预防怀孕妇女使用药物但不希望或无法在怀孕期间停止使用时胎儿暴露于药物。
• Technology for the Preparation of Microparticles
  申请人：Malakhov Michael

  公开号：US20090098207A1

  公开（公告）日：2009-04-16

  Microspheres are produced by contacting a solution of a macromolecule or small molecule in a solvent with an antisolvent and a counterion, and chilling the solution. The microspheres are useful for preparing pharmaceuticals, nutraceuticals, cosmetic products and the like of defined dimensions.

  微球是通过将溶液中的大分子或小分子与抗溶剂和对离子接触，并冷却溶液而制备的。这些微球可用于制备具有明确定义尺寸的药物、营养保健品、化妆品等产品。
• Analgesics, anaesthetics, antifoulants, aversants, irritants, incapacitants and compositions containing the same
  申请人：Blum Mel

  公开号：US20070225515A1

  公开（公告）日：2007-09-27

  Compounds and compositions the same. Method of making the compounds. The compounds and/or compositions used as an analgesic, anaesthetic, antifoulant, aversant, irritant, sternutator, neurodegenerator, counter irritant (delayed), rubifaciant, stomachic, fungicide, insecticide, preservative, circulatory stimulant, cardio-protective agent, immune booster, decongestant, anti-inflammatory agent, incapacitant, biocide, mildewcide, pharmaceutical, repellent, flavorant, carminative, antismoking agent, and/or antithrombotic agent. One of the compounds being lidocaine nonivamide. The compositions comprising one or more of: the compounds, one or more of an antioxidant, a UV absorber, and one or more biocides such as, for example, OBPA.

  化合物和组合物相同。制备这些化合物的方法。这些化合物和/或组合物用作止痛剂、麻醉剂、防污剂、驱避剂、刺激剂、喷鼻剂、神经变性剂、延迟性刺激剂、红斑剂、胃药、杀真菌剂、杀虫剂、防腐剂、循环刺激剂、心脏保护剂、免疫增强剂、通窍剂、抗炎剂、致残剂、生物杀灭剂、霉菌杀灭剂、药用、驱虫剂、调味剂、驱风剂、抗吸烟剂和/或抗血栓剂。其中一种化合物是利多卡因辛烷酸酯。组合物包括：这些化合物中的一种或多种、一种或多种抗氧化剂、一种或多种紫外线吸收剂，以及一种或多种生物杀灭剂，例如OBPA。
• Odorless formulation for treating mucosal discontinuities
  申请人：——

  公开号：US20040132810A1

  公开（公告）日：2004-07-08

  The present invention includes a method for making a formulation for treating mucosal discontinuities, comprising: providing phenolic compounds and treating the purified phenolic compounds with sulfuric acid to make sulfonic acids and sulfonate salts. The present invention also includes formulations prepared by the method.

  本发明涉及一种用于制备治疗黏膜不连续的配方的方法，包括：提供酚类化合物，并用硫酸处理纯化的酚类化合物以制备磺酸和磺酸盐。本发明还包括通过该方法制备的配方。
• Reaction Mechanism for Cocaine Esterase-Catalyzed Hydrolyses of (+)- and (−)-Cocaine: Unexpected Common Rate-Determining Step
  作者：Junjun Liu、Xinyun Zhao、Wenchao Yang、Chang-Guo Zhan

  DOI：10.1021/jp200975v

  日期：2011.5.5

  (+)-cocaine consists of nucleophilic attack of the hydroxyl group of Ser117 on the carbonyl carbon of (+)-cocaine benzoyl ester and the dissociation of (+)-cocaine benzoyl ester. The first reaction step of deacylation of (+)-cocaine, which is identical to that of (−)-cocaine, is rate-determining, indicating that CocE-catalyzed hydrolyses of (+)- and (−)-cocaine have a common rate-determining step.

  已进行第一性原理量子力学/分子机械自由能计算，以检查可卡因酯酶 (CocE) 催化 (+)-可卡因水解的催化机制，并与 CocE 催化 (−)-可卡因水解进行比较。研究表明，(+)-可卡因的酰化过程由Ser117的羟基对(+)-可卡因苯甲酰酯的羰基碳的亲核攻击和(+)-可卡因苯甲酰酯的解离组成。 (+)-可卡因脱酰化的第一个反应步骤与 (−)-可卡因相同，是限速反应，表明 CocE 催化的 (+)- 和 (−)-可卡因水解有一个共同点速率决定步骤。计算结果预测 CocE 对 (+)-可卡因的催化速率常数应与 CocE 对 (−)-可卡因的催化速率常数相同，而人丁酰胆碱酯酶催化 (+)- 和 (+)- 和 (-)- 可卡因的水解之间存在显着差异。 (−)-可卡因。该预测已通过 CocE 催化 (+)-可卡因水解与 CocE 催化 (−)-可卡因水解的实验动力学分析得到证实。所确定的共同限速步