2-(1-hydroxy-2-chloroethyl)-furan | 99418-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(1-hydroxy-2-chloroethyl)-furan
• 英文别名: rac-2-chloro-1-(2-furyl)ethanol；2-chloro-1-(furan-2-yl)ethanol；2-chloro-1-fur-2-yl-ethanol；(+)-2-chloro-1-(2'-furyl)ethanol；2-Chloro-1-(furan-2-yl)ethan-1-ol
• CAS: 99418-39-0
• 化学式: C₆H₇ClO₂
• mdl: MFCD15145992
• 分子量: 146.573
• InChiKey: YUBBGHLHXUVOHT-UHFFFAOYSA-N

物化性质

• 沸点：
  196.5±25.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

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：
  0.333
• 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：

  2-(1-hydroxy-2-chloroethyl)-furan 在 Pseudomonas cepacia lipase 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 115.0h， 生成 (S)-2-氯-1-(呋喃-2-基)乙烷-1-醇
  参考文献：
  名称：

  Chemoenzymatic synthesis of both enantiomers of 2-chloro-1-(2-furyl)ethanol

  摘要：

  Enzyme catalyzed transesterification of rac-2-chloro-1-(2-furyl)ethanol rac-1 using vinyl acetate afforded the enantiomers of 2-chloro-1-(2-furyl)ethanol 1 and 2-chloro-1-(2-furyl)ethyl acetate 2 in high enantiomeric excess. Several lipases were used for the kinetic resolution of racemic 2-chloro-1-(2-furyl)ethanol 1, in which the lipases from Pseudomonas cepacia, Candida antarctica and Candida cylindracea displayed high enantioselectivity towards 1. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.007
• 作为产物：
  描述：

  [[1-(2-furyl)ethenyl]oxy]tri-isopropylsilane 在 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 cerium(III) chloride 、 氢氟酸 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 10.0h， 生成 2-(1-hydroxy-2-chloroethyl)-furan
  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。
• 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。
• Process for producing optically active halohydrin compound
  申请人：——

  公开号：US20040082820A1

  公开（公告）日：2004-04-29

  A process of preparing an optically active halohydrin compound characterized by comprising asymmetric hydrogen transfer reduction of an &agr;-haloketone compound in the presence of a group 9 transition metal compound having a substituted or unsubstituted cyclopentadienyl group and an optically active diamine compound. The asymmetric hydrogen transfer reduction is preferably conducted in the presence of a base.

  一种制备光学活性卤代醇化合物的方法，其特征在于在存在具有取代或未取代环戊二烯基基团和光学活性二胺化合物的9族过渡金属化合物的情况下进行α-卤代酮化合物的不对称氢转移还原。最好在碱存在下进行不对称氢转移还原。
• Process to produce enantiomerically enriched 1-aryl-and 1-heteroaryl-2-aminoethanols
  申请人：Pfizer, Inc.

  公开号：US20040236151A1

  公开（公告）日：2004-11-25

  The invention relates to a method of preparing enantiomerically enriched amino alcohols of Formula I 1 wherein the variable R1, R2, and R3 are defined herein.

  本发明涉及一种制备对映体富集的式I1的氨基醇的方法，其中变量R1、R2和R3在此处定义。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE HALOHYDRIN COMPOUND
  申请人：Ajinomoto Co., Inc.

  公开号：EP1346972A1

  公开（公告）日：2003-09-24

  A process of preparing an optically active halohydrin compound characterized by comprising asymmetric hydrogen transfer reduction of an α-haloketone compound in the presence of a group 9 transition metal compound having a substituted or unsubstituted cyclopentadienyl group and an optically active diamine compound. The asymmetric hydrogen transfer reduction is preferably conducted in the presence of a base.

  一种制备光学活性卤代化合物的工艺，其特征在于包括在具有取代或未取代环戊二烯基团的第9族过渡金属化合物和光学活性二胺化合物存在下，对α-卤代酮化合物进行不对称氢转移还原。不对称氢转移还原最好在碱存在下进行。