(S)-2-氯-1-(呋喃-2-基)乙烷-1-醇 | 439807-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: (S)-2-氯-1-(呋喃-2-基)乙烷-1-醇
• 英文名称: (S)-2-(1-hydroxy-2-chloroethyl)-furan
• 英文别名: (S)-2-chloro-1-(2-furyl)ethanol；(S)-2-chloro-1-fur-2-yl-ethanol；(S)-1-(furan-2-yl)-2-chloroethanol；(S)-1-(2-furyl)-2-chloroethanol；S-1-(2-furyl)-2-chloroethanol；(1S)-2-chloro-1-(2-furyl)ethanol；(1S)-2-chloro-1-(furan-2-yl)ethanol
• CAS: 439807-14-4
• 化学式: C₆H₇ClO₂
• 分子量: 146.573
• InChiKey: YUBBGHLHXUVOHT-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  (S)-2-氯-1-(呋喃-2-基)乙烷-1-醇 在 氢氧化钾 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 (R)-1-(2-furyl)-2-(methylamino)ethanol
  参考文献：
  名称：

  Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

  摘要：

  As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.017
• 作为产物：
  描述：

  2-乙酰基呋喃 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 (1R,2R)-(-)-N-(对甲基苯磺酰基)-1,2-二苯基乙二胺 N-氯代丁二酰亚胺 、 甲酸 、 氢氟酸 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.25h， 生成 (S)-2-氯-1-(呋喃-2-基)乙烷-1-醇
  参考文献：
  名称：

  Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

  摘要：

  As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.017

文献信息

• [EN] PROCESS TO PRODUCE ENANTIOMERICALLY ENRICHED 1-ARYL- AND 1-HETEROARYL-2-AMINOETHANOLS<br/>[FR] PROCEDE DE PREPARATION D'1-ARYL- ET D'1-HETEROARYL-2-AMINOETHANOLS ENRICHIS EN ENANTIOMERES
  申请人：UPJOHN CO

  公开号：WO2004085414A1

  公开（公告）日：2004-10-07

  The invention relates to a method of preparing enantiomerically enriched amino alcohols of Formula (I) wherein the variable R1, R2, and R3 are defined herein.

  这项发明涉及一种制备式(I)的对映体富集氨基醇的方法，其中变量R1、R2和R3在此处被定义。
• Pyridoquinoxaline antivirals
  申请人：——

  公开号：US20030207877A1

  公开（公告）日：2003-11-06

  The present invention provides a compound of formula I 1 or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are as defined in the specification. The compounds are useful for the treatment of viral infections.

  本发明提供了一种具有以下结构的化合物I或其药学上可接受的盐，其中R1、R2和R3如规范中定义。这些化合物对于治疗病毒感染是有用的。
• Synthesis of enantiopure chloroalcohols by enzymatic kinetic resolution
  作者：Robert M. Haak、Chiara Tarabiono、Dick B. Janssen、Adriaan J. Minnaard、Johannes G. de Vries、Ben L. Feringa

  DOI：10.1039/b613937j

  日期：——

  3-Alkenyl and heteroaryl chloroalcohols have been obtained in excellent enantiomeric excess (>99%) by enzymatic kinetic resolution using the haloalcohol dehalogenase HheC. Yields were close to the theoretical maximum for all substrates employed. Furthermore, the applicability of this methodology on multigram scale has been established.

  通过使用卤醇脱卤酶HheC进行酶促动力学拆分，成功获得了具有优异对映体过剩（>99%）的3-烯基和杂芳基氯醇。所有使用底物的产率均接近理论最大值。此外，该方法在大规模多克重应用中的适用性也得到了验证。
• A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium–diamine catalyst
  作者：Takayuki Hamada、Takayoshi Torii、Kunisuke Izawa、Takao Ikariya

  DOI：10.1016/j.tet.2004.06.076

  日期：2004.8

  A practical method for the synthesis of optically active aromatic epoxides has been developed via the formation of optically active α-chlorinated alcohols and intramolecular etherification. Optically active alcohols with up to 99% ee can be obtained from the asymmetric reduction of aromatic ketones with a substrate/catalyst ratio of 1000–5000 using a formic acid/triethylamine mixture containing a well-defined

  通过形成光学活性的α-氯化醇和分子内醚化，已经开发了一种合成光学活性的芳族环氧化物的实用方法。使用含有明确定义的手性Rh络合物Cp * RhCl [（[R， [R）-Tsdpen]。由于二胺基Cp * Rh（III）氢化物配合物的配位饱和特性，用手性Rh催化剂不对称还原α-氯化芳族酮的特征是快速且羰基选择性转化。还原的结果受酮底物的结构以及氢源（如甲酸或2-丙醇）的影响很大。无需特殊纯化即可在该反应中使用市售的试剂和溶剂。一锅法或两锅法的这种环氧化物合成方法是实用的，对于从α-氯代酮大规模生产旋光性苯乙烯氧化物特别有用。
• Chloroperoxidase-Catalyzed Achmatowicz Rearrangements
  作者：Daniel Thiel、Fabian Blume、Christina Jäger、Jan Deska

  DOI：10.1002/ejoc.201800333

  日期：2018.6.7

  HUOM! TAMA MANUSKA ON TILASSA CLOSED KUNNES ARTIKKELI ON JULKAISTU JA JULKAISUVIIVE MAARITELTY KUSTANTAJAN JULKAISUPAIVASTA ALKAEN. The manuscript is "closed" until the article has been published and the embargo date can be defined.

  呼！蒂拉萨岛上的 TAMA MANUSKA 关闭了 JULKAISTU JA JULKAISUVIIVE MAARITELTY KUSTANTAJAN JULKAISUPAIVASTA ALKAEN 的 KUNNES ARTIKKELI。在文章发表并且可以确定禁运日期之前，手稿处于“关闭”状态。