trans-2-ethyl-3-hydroxytetrafuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: trans-2-ethyl-3-hydroxytetrafuran
• 英文别名: rac-2-ethyl-3-hydroxy-tetrahydrofuran；(2S,3R)-2-ethyloxolan-3-ol
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: XGCFBZRHYYBHQA-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2-ethyl-3-hydroxytetrafuran 在 三甲基氯硅烷 、 水 、 sodium iodide 作用下， 生成
  参考文献：
  名称：

  Stereocontrolled Formation of Functionalized erythro-1,2-Diols via Hydroboration of 2-Alkyl-4,5-dihydrofurans

  摘要：

  trans-2-Alkyl-3-hydroxytetrahydrofurans, prepared by the stereospecific hydroboration / oxidation reaction of 2-alkyl-4,5-dihydrofurans, were regioselectively cleaved with (CH3)3SiCl / NaI to afford 1-iodo-erythro-3,4-diols in CH3CN or the corresponding acetonide derivatives in CH3COCH3.

  DOI：

  10.3987/com-93-6428
• 作为产物：
  描述：

  反式-3-己烯-1-醇 在 吡啶 、 sodium dihydrogenphosphate 、 硫酸 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 36.25h， 生成 trans-2-ethyl-3-hydroxytetrafuran
  参考文献：
  名称：

  卤代烷基环氧化物的酶促对映聚合转化

  摘要：

  使用整个细菌细胞的环氧水解酶活性对 2,3-二取代外消旋-顺-和外消旋-反-卤代烷基环氧化物 1a-8a 进行生物催化水解，得到相应的邻位二醇 1b-8b 作为中间体；这些（自发地）经历闭环以通过酶触发的级联反应产生环状产物 1c-6c。特别是，顺式构型的底物（1a、3a、5a、7a）以对映收敛方式转化，导致从外消旋体中形成 100% des 和高达 92% ees 的单一立体异构产物。

  DOI：

  10.1002/1099-0690(200112)2001:23<4537::aid-ejoc4537>3.0.co;2-e

文献信息

• Reaction of homoallylic alcohols with NaIO4/NaHSO3 reagent—synthesis of alkyl substituted tetrahydrofuran derivatives
  作者：Yoshio Okimoto、Daisuke Kikuchi、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1016/s0040-4039(00)01819-0

  日期：2000.12

  Treatment of homoallylic alcohols with NaIO4/NaHSO3 reagent in aqueous t-BuOH under mild conditions produced tetrahydrofuran derivatives together with iodohydrins in a stereospecific manner. The reaction pathways of the formation of tetrahydrofurans from trans- and cis-homoallylic alcohols were found to be different. The present method provides a new approach to various alkylated tetrahydrofuran derivatives

  在温和的条件下，在水溶液中用NaIO 4 / NaHSO 3试剂在t- BuOH水溶液中处理均烯丙基醇，可生成四氢呋喃衍生物和碘醇，并以立体特异性方式生成。从四氢呋喃形成的反应途径的反式-和顺-homoallylic醇被发现是不同的。本方法为各种烷基化四氢呋喃衍生物提供了一种新方法。
• Borinic Acid-Catalyzed, Regioselective Ring Opening of 3,4-Epoxy Alcohols
  作者：Grace Wang、Graham E. Garrett、Mark S. Taylor

  DOI：10.1021/acs.orglett.8b02295

  日期：2018.9.7

  Diarylborinic acids (Ar2BOH) catalyze the C3-selective ring opening of 3,4-epoxy alcohols with aniline, dialkylamine and arenethiol nucleophiles. The regiochemical outcome is consistent with a catalytic tethering mechanism in which the borinic acid interacts with both the electrophile and the nucleophile. The rate acceleration resulting from this induced intramolecularity effect is sufficient to overcome

  二芳基硼酸（Ar 2 BOH）与苯胺，二烷基胺和槟榔亲核试剂一起催化3,4-环氧醇的C3选择性开环。区域化学结果与催化性束缚机制一致，在该机制中，硼酸与亲电试剂和亲核试剂都相互作用。由这种诱导的分子内效应产生的速率加速足以克服空间偏倚，否则将有利于取代的环氧醇的C 4选择性打开。
• Synthesis of tetrahydrofurans by regio- and stereoselective cyclization of epoxyalcohols using magnesium halide
  作者：Michinori Karikomi、Shigeru Watanabe、Yukino Kimura、Tadao Uyehara

  DOI：10.1016/s0040-4039(02)00042-4

  日期：2002.2

  A Nobel synthetic method for several tetrahydrofuran derivatives by intramolecular cyclization of epoxyalchols is described. The presence of a catalytic amount of magnesium halide altered the regio- and stereoselectivity of the cyclization reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Enzyme-Triggered Enantioconvergent Transformation of Haloalkyl Epoxides
  作者：Sandra F. Mayer、Andreas Steinreiber、Romano V. A. Orru、Kurt Faber

  DOI：10.1002/1099-0690(200112)2001:23<4537::aid-ejoc4537>3.0.co;2-e

  日期：2001.12

  rac-trans-haloalkyl epoxides 1a−8a using the epoxide hydrolase activity of whole bacterial cells furnished the corresponding vicinal diols 1b−8b as intermediates; these (spontaneously) underwent ring closure to yield cyclic products 1c−6c through an enzyme-triggered cascade reaction. In particular, cis-configured substrates (1a, 3a, 5a, 7a) were transformed in an enantioconvergent fashion, which resulted

  使用整个细菌细胞的环氧水解酶活性对 2,3-二取代外消旋-顺-和外消旋-反-卤代烷基环氧化物 1a-8a 进行生物催化水解，得到相应的邻位二醇 1b-8b 作为中间体；这些（自发地）经历闭环以通过酶触发的级联反应产生环状产物 1c-6c。特别是，顺式构型的底物（1a、3a、5a、7a）以对映收敛方式转化，导致从外消旋体中形成 100% des 和高达 92% ees 的单一立体异构产物。
• Stereocontrolled Formation of Functionalized erythro-1,2-Diols via Hydroboration of 2-Alkyl-4,5-dihydrofurans
  作者：Roger Amouroux、Abdelmalik Slassi、Christine Saluzzo

  DOI：10.3987/com-93-6428

  日期：——

  trans-2-Alkyl-3-hydroxytetrahydrofurans, prepared by the stereospecific hydroboration / oxidation reaction of 2-alkyl-4,5-dihydrofurans, were regioselectively cleaved with (CH3)3SiCl / NaI to afford 1-iodo-erythro-3,4-diols in CH3CN or the corresponding acetonide derivatives in CH3COCH3.