(S)-(+)-2-bromo-1-(7-ethyl-benzofuran-2-yl)ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (S)-(+)-2-bromo-1-(7-ethyl-benzofuran-2-yl)ethanol
• 英文别名: (S)-(+)-2-bromo-1-(7-ethylbenzofuran-2-yl)ethanol；(S)-2-bromo-1-(7-ethylbenzofuran-2-yl)ethanol；2-bromo-1-(7-ethylbenzofuran-2-yl)ethanol；(1S)-2-bromo-1-(7-ethyl-1-benzofuran-2-yl)ethanol
• 化学式: C₁₂H₁₃BrO₂
• 分子量: 269.138
• InChiKey: GADFNTQQKZYNSL-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙基苯酚 在 potassium carbonate 、 溶剂黄146 、 pyridinium hydrobromide perbromide 、 三乙胺 、 (-)-diisopinocamphenylborane chloride 、 magnesium chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 34.0h， 生成 (S)-(+)-2-bromo-1-(7-ethyl-benzofuran-2-yl)ethanol
  参考文献：
  名称：

  Asymmetric synthesis of (S)-bufuralol and a propafenone analogue

  摘要：

  Asymmetric synthesis of (S)-bufuralol of 87% ee from 3-ethyl-2-hydroxybenzaldehyde, via the reduction of 2-bromo-1-(7-ethylbenzofuran-2-yl)ethanone with (-)-B-chlorodiisopinocampheylborane as the key step, followed by cyclization of the product bromohydrin to the corresponding epoxide and treatment with tert-butylamine, is described. (S)-1-(3-Phenethylbenzofuran-2-yl)-2-propylaminoethanol of 73% ee, a propafenone analogue, was prepared following the same approach. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00276-3

文献信息

• New chemo-enzymatic approaches for the synthesis of (R)- and (S)-bufuralol
  作者：Botond Nagy、Norbert Dima、Csaba Paizs、Jürgen Brem、Florin Dan Irimie、Monica Ioana Toşa

  DOI：10.1016/j.tetasy.2014.08.002

  日期：2014.10

  molecules. While the (S)-isomer with a higher β-blocking activity is recommended for hypertension treatment, the (R)-enantiomer can be used as marker of hepatic activity. In this paper two new alternative approaches are described for their chemo-enzymatic synthesis, providing both highly enantiomerically enriched stereoisomers of the target molecule (ee 96–98%). One route is based on the baker’s yeast

  丁呋洛尔的两种对映体是药学上重要的分子。虽然（小号）具有更高的β阻断活性异构体被推荐用于高血压治疗中，（[R ）-对映体可被用作肝活性的标志物。在本文中两个新的替代方法是为他们的化学-酶促合成所描述的，提供目标分子的两个高度富含对映体的立体异构体（ee值96-98％）。一条路线是基于介导的α取代的酮的立体选择性生物转化，并且在外消旋溴乙醇的脂肪酶介导的动力学拆分中的另一个的面包酵母。
• Effect of chemical structure of benzofuran derivatives and reaction conditions on enantioselective properties of <i>Aureobasidium pullulans</i> microorganism contained in Boni Protect antifungal agent
  作者：Renata Kołodziejska、Renata Studzińska、Agnieszka Tafelska‐Kaczmarek、Hanna Pawluk、Bartosz Stasiak、Marcin Kwit、Alina Woźniak

  DOI：10.1002/chir.23180

  日期：2020.3

  the highest selectivity. Aureobasidium pullulans microorganism is less effective in the reduction of unsymmetrical halomethyl ketones. The presence of a heteroatom in the alkyl group significantly decreases the selectivity of the process. Finally, as a result of the preferred hydride ion transfer from the dihydropyridine ring of the cofactor to the carbonyl double bond on the re side, secondary alcohols

  羰基化合物的生物有机不对称还原是生产手性醇的最重要的基本和实际反应之一。研究了在抗真菌Boni保护剂中存在的酵母样真菌金黄色葡萄球菌支链淀粉存在下，苯并呋喃衍生物的前手性酮的立体选择性生物还原。生物转化是在中等条件下在水相和两相系统中进行的，没有生物试剂的繁殖。尽管化学结构相似，但每种酮都以不同的效率和选择性被还原。这些结果的原因之一是在支链淀粉中存在一整套氧化还原酶对前手性底物结构的最小变化敏感的细胞。不对称甲基酮以最高的选择性进行了生物转化。金黄芽孢杆菌微生物在减少不对称卤代甲基酮方面不太有效。烷基中杂原子的存在显着降低了该方法的选择性。最后，如从辅因子对羰基双键的二氢吡啶环的优选氢化物离子转移的结果重新侧，所述的仲醇小号和- [R用中度到高对映选择性（55-99％）中获得的配置。
• Enantioselective reduction of benzofuryl halomethyl ketones: asymmetric synthesis of (R)-bufuralol
  作者：Marek Zaidlewicz、Agnieszka Tafelska-Kaczmarek、Andrzej Prewysz-Kwinto

  DOI：10.1016/j.tetasy.2005.08.012

  日期：2005.10

  Enantioselective reduction of representative 2-(bromoacetyl)- and 2-(chloroacetyl)benzofurans with (-)-B-chloro-diisopinocampheylborane and by transfer hydrogenation with formic acid/triethylamine in the presence of RhCl[R,R-TsD-PEN](C5Me5) is described. Transfer hydrogenation of the chloro ketones produced the corresponding chlorohydrins of >= 95% ee. (R)-Bufuralol of 96% ce was prepared from the corresponding chloro ketone by transfer hydrogenation-substitution. (c) 2005 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of (S)-bufuralol and a propafenone analogue
  作者：Marek Zaidlewicz、Agnieszka Tafelska-Kaczmarek、Andrzej Prewysz-Kwinto、Aldona Chechłowska

  DOI：10.1016/s0957-4166(03)00276-3

  日期：2003.6

  Asymmetric synthesis of (S)-bufuralol of 87% ee from 3-ethyl-2-hydroxybenzaldehyde, via the reduction of 2-bromo-1-(7-ethylbenzofuran-2-yl)ethanone with (-)-B-chlorodiisopinocampheylborane as the key step, followed by cyclization of the product bromohydrin to the corresponding epoxide and treatment with tert-butylamine, is described. (S)-1-(3-Phenethylbenzofuran-2-yl)-2-propylaminoethanol of 73% ee, a propafenone analogue, was prepared following the same approach. (C) 2003 Elsevier Science Ltd. All rights reserved.