(R)-5-溴萘普生 | 92471-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (R)-5-溴萘普生
• 中文别名: （R）-5-溴萘普生
• 英文名称: 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid
• 英文别名: (2R)-2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid；2(R)-(-)-(5-bromo-6-methoxy-2-naphthyl)propanoic acid；R(-)-2-(5-bromo-6-methoxy-2-naphthyl)-propionic acid；(R)-5-Bromo Naproxen；(2R)-2-(5-bromo-6-methoxynaphthalen-2-yl)propanoic acid
• CAS: 92471-85-7
• 化学式: C₁₄H₁₃BrO₃
• 分子量: 309.159
• InChiKey: JZRWXNBIQCMXSU-MRVPVSSYSA-N

物化性质

• 沸点：
  446.2±30.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-溴萘普生 在 镍 氢氧化钾 、 一水合肼 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (R)-萘普生
  参考文献：
  名称：

  立体收敛策略，用于合成对映体纯的（R）-（-）和（S）-（+）-2-（6-甲氧基-2-萘基）-丙酸（萘普生）

  摘要：

  设计了一种合成策略，用于解决与使用手性助剂有关的非对映选择性缺陷。这种缺陷的影响是最终产物的对映体纯度较低。

  DOI：

  10.1016/s0040-4020(01)81319-3
• 作为产物：
  描述：

  2-(5-Bromo-6-methoxynaphthalen-2-yl)propanoyl chloride 在 Candida cylindraceae lipase 作用下， 以 phosphate buffer 、 二氯甲烷 为溶剂， 反应 105.0h， 生成 (R)-5-溴萘普生
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009

文献信息

• Process for the preparation of optically active alpha-acrylalkanoic
  申请人：Zambon Spa

  公开号：US04810819A1

  公开（公告）日：1989-03-07

  A new enantioselective process is described for preparing optically active alpha-arylalkanoic acids by: (a) halogenation on the aliphatic carbon atom alpha to the ketal group, of ketals of formula ##STR1## in which Ar represents an aryl, optionally substituted; R represents a C.sub.1 -C.sub.4 alkyl; R.sub.1 and R.sub.2, represents a hydroxy, a O.sup.- M.sup.+, OR.sub.3 or NR.sub.4 R.sub.5 group; the carbon atoms indicated by an asterisk both simultaneously are in (R) or (S) configuration. This reaction is diastereoselective, so that a mixture of alpha-haloketals is obtained in which one of the two epimers prevails, and generally strongly prevails, over the other. (b) rearrangement of the haloketals of formula ##STR2## in which X is Cl, Br or I to alpha-arylalkanoic acids in a single stage or in two successive stages, by way of esters of formula ##STR3## The compounds (A) and (C) are all new compounds. The rearrangement step (b) may be performed under new, inventive conditions. The esters of formula (C) have pharmacological activity analogous to that of the corresponding alpha-arylalkanoic acids.

  描述了一种新的对映选择性过程，用于通过以下方法制备光学活性的α-芳基烷基酸：(a) 在磷酸酯基团α位于脂肪碳原子上的卤代反应，其中磷酸酯的化学式为##STR1## 其中Ar代表芳基，可选择性取代；R代表C.sub.1 -C.sub.4烷基；R.sub.1和R.sub.2代表羟基、O.sup.- M.sup.+、OR.sub.3或NR.sub.4 R.sub.5基团；星号标记的碳原子同时处于(R)或(S)构型。该反应是非对映选择性的，因此获得了α-卤代磷酸酯混合物，其中两个对映体中的一个占优势，通常明显占优势。 (b) 将化学式为##STR2## 的卤代磷酸酯重新排列为α-芳基烷基酸，在单阶段或两个连续阶段中，通过化学式为##STR3## 的酯。化合物(A)和(C)均为新化合物。重新排列步骤(b)可以在新的、创新的条件下进行。化学式(C)的酯具有类似于相应α-芳基烷基酸的药理活性。
• Fast and efficient tritium labelling of the nonsteroidal anti-inflammatory drugs naproxen, tolmetin, and zomepirac
  作者：Steen K. Johansen、Lone Sørensen、Lars Martiny

  DOI：10.1002/jlcr.950

  日期：2005.7

  Fast and efficient tritium labelling of the nonsteroidal anti-inflammatory drugs naproxen, tolmetin and zomepirac is reported. Naproxen along with its (R)-enantiomer were labelled by catalytic tritium–halogen exchange of the corresponding 5-bromo derivatives providing [3H]naproxen with a specific activity of 25.4 Ci/mmol. Tolmetin and zomepirac were labelled by the hydrogen isotope exchange reaction using Crabtree's catalyst. This provided [3H]tolmetin and [3H]zomepirac with specific activities of 80.8 and 64.3 Ci/mmol, respectively. All compounds were obtained in high radiochemical purity (>98%). Copyright © 2005 John Wiley & Sons, Ltd.

  报告了对非甾体抗炎药萘普生、托美汀和佐美吡拉进行快速高效氚标记的情况。萘普生及其(R)-对映体是通过相应的 5-溴衍生物的催化氚卤交换进行标记的，其[3H]萘普生的比活度为 25.4 Ci/mmol。使用 Crabtree 催化剂通过氢同位素交换反应对托美汀和佐美匹拉克进行了标记。这样得到的[3H]托美汀和[3H]佐美匹拉克的比活度分别为 80.8 和 64.3 Ci/mmol。所有化合物的放射化学纯度都很高（>98%）。Copyright © 2005 John Wiley & Sons, Ltd. All Rights Reserved.
• Process for the preparation of optically active alpha-arylalkanoic acids and intermediates thereof
  申请人：ZAMBON S.p.A.

  公开号：EP0158913A2

  公开（公告）日：1985-10-23

  A new enantioselective process is described for preparing optically active alpha-arylalkanoic acids by: a) halogenation on the aliphatic carbon atom alpha to the ketal group, of ketals of formula in which Ar represents an aryl, optically substituted; R represents a C1-C4 alkyl; R, and R2, represent a hydroxy, a O-M+, OR3 or NR4R5 group; the carbon atoms indicated by an asterisk both simultaneously are in (R) or (S) configuration.This reaction is diastereoselective, so that a misture of alpha-haloketals is obtained in which one of the two epimers prevails, and generally strongly prevails, over the other. b) rearrangement of the haloketals of formula in which X is CI, Br or I to alpha-arylalkanoic acids in a single stage or in two successive stages, by way of esters of formula The compounds (A) and (C) are all new compounds. The rearrengement step (b) may be performed under new, inventive conditions. The esters of formula (C) have pharmacological activity analogous to that of the corresponding alpha-arylalkanoic acids.

  介绍了一种通过以下方法制备光学活性α-芳基烷酸的对映体选择性新工艺： a) 卤化式如下的酮的脂肪族碳原子α到酮基 其中 Ar 代表被光学取代的芳基； R 代表 C1-C4 烷基； R 和 R2 代表羟基、O-M+、OR3 或 NR4R5。 基团；星号表示的碳原子同时在 该反应具有非对映选择性。 该反应具有非对映选择性，因此可以得到α-卤代金属的畸变体。 该反应具有非对映选择性，因此可以得到α-卤代缩酮的混合物。 该反应具有非对映选择性，因此在得到的α-卤代金属错置物中，两种表聚物中的一种占优势，而且通常比另一种强。 b) 式中α-卤代金属的重排 式中 X 为 CI、Br 或 I 的卤代烃与 α-芳基烷酸在一个阶段或连续两个阶段的重排，通过式中的酯 化合物(A)和(C)均为新化合物。重整步骤 (b) 可在新的创造性条件下进行。 式（C）的酯类具有类似于相应α-芳基烷酸的药理活性。
• Tartaric acid, an efficient chiral auxiliary: new asymmetric synthesis of 2-alkyl-2-arylacetic acids
  作者：Graziano Castaldi、Silvia Cavicchioli、Claudio Giordano、Fulvio Uggeri

  DOI：10.1021/jo00390a013

  日期：1987.7
• GIORDANO, CLAUDIO;CASTALDI, GRAZIANO;CAVICCHIOLI, SILVIA;VILLA, MARCO, TETRAHEDRON, 45,(1989) N3, C. 4243-4252
  作者：GIORDANO, CLAUDIO、CASTALDI, GRAZIANO、CAVICCHIOLI, SILVIA、VILLA, MARCO

  DOI：——

  日期：——