(2R,4S)-hex-5-ene-2,4-diol | 263253-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S)-hex-5-ene-2,4-diol
• 英文别名: (2R,4S)-5-hexene-2,4-diol
• CAS: 263253-11-8
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: YCMQFCBQAPDWJW-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4S)-hex-5-ene-2,4-diol 在 碘 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 三乙胺 作用下， 以 正己烷 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 7.5h， 生成
  参考文献：
  名称：

  Total Synthesis of Amphirionin-4

  摘要：

  An expeditious enantioselective total synthesis of amphirionin-4, a remarkably potent promoter of the proliferation of ST-2 cells, has been achieved from (+/-)-(E)-1,4-hexadien-3-ol by an 8-pot sequence that features the Sharpless kinetic resolution, iodoetherification, and the CBS reduction to install the stereocenters, utilization of four one pot transformations to streamline the synthetic process, and the Stille coupling reaction at nearly the center of the target molecule to complete the total synthesis.

  DOI：

  10.1021/acs.orglett.6b00883
• 作为产物：
  描述：

  (-)-(S)-3-hydroxypent-4-enoic acid methoxymethylamide 在 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 溶剂黄146 、 乙腈 为溶剂， 生成 (2R,4S)-hex-5-ene-2,4-diol
  参考文献：
  名称：

  Stereoselective total synthesis of stagonolide-C

  摘要：

  The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.015

文献信息

• Preparation of Optically Active Allylic Hydroperoxy Alcohols and 1,3-Diols by Enzyme-Catalyzed Kinetic Resolution and Photooxygenation of Chiral Homoallylic Alcohols
  作者：Waldemar Adam、Chantu R. Saha-Möller、Katharina S. Schmid

  DOI：10.1021/jo9915630

  日期：2000.3.1

  photooxygenation of the racemic homoallylic alcohols 1 gave the racemic hydroperoxy alcohols 2, which have subsequently been kinetically resolved by horseradish peroxidase (HRP); alternatively, first the lipase-catalyzed resolution afforded the optically active homoallylic alcohols 1 and subsequent photooxygenation led to the enantiomerically enriched hydroperoxy alcohols 2.

  3-氢过氧-4-戊烯-1-醇2a，b以及它们相应的4-戊烯-1,3-二醇4a，b的所有四种可能的对映异构体都是首次以高对映体纯度制备（最高达98 ％ee）并根据两种不同的制备方法制备它们：首先，外消旋均烯丙基醇1的光氧合得到外消旋氢过氧醇2，其随后被辣根过氧化物酶（HRP）动力学分解；或者，首先通过脂肪酶催化的拆分得到旋光的均烯丙基醇1，随后进行光氧合生成对映异构体富集的氢过氧醇2。
• Chemo-enzymatic asymmetric total synthesis of stagonolide-C
  作者：Nandan Jana、Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2009.10.007

  日期：2009.11

  The naturally occurring phytotoxic noneolide stagonolide-C has been synthesized by a chemo-enzymatic approach. Two key intermediates have been synthesized by applying a metal-enzyme combined DKR (dynamic kinetic resolution) strategy, followed by RCM (ring-closing metathesis) to afford the target compound in an efficient way. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of bis-tetrahydrofuran subunit of (−)-neopallavicinin
  作者：Martin Markovič、Marianna Ďuranová、Peter Koóš、Peter Szolcsányi、Tibor Gracza

  DOI：10.1016/j.tet.2013.03.100

  日期：2013.5

  The stereospecific Pd/Cu-catalysed oxycarbonylation of syn/anti-hex-5-ene-2,4-diols 7/8 was used as a key step in the synthesis of bicyclic lactones 5 and 6. Eventually, the major intermediate 5 was transformed to the bis-tetrahydrofuran subunit of naturally occurring diterpenoid (-)-neopallavicinin 2. The target compound 3E was thus prepared in 7.5% overall yield over eight steps starting from commercially available (R)-methyl-3-hydroxybutanoate 9. (C) 2013 Elsevier Ltd. All rights reserved.
• Paquette, Leo A., Synthesis, 2003, # 5, p. 765 - 774
  作者：Paquette, Leo A.

  DOI：——

  日期：——
• Stereoselective synthesis of functionalized erythro/1,3-diols
  作者：Peter Mohr、Christoph Tamm

  DOI：10.1016/s0040-4039(00)95736-8

  日期：1987.1