(S)-3-vinylpent-4-ene-2,3-diol | 163259-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-vinylpent-4-ene-2,3-diol
• 英文别名: (2S)-3-ethenylpent-4-ene-2,3-diol
• CAS: 163259-66-3
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: RRJRBTVAMSGCFB-LURJTMIESA-N

物化性质

• 沸点：
  219.9±35.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (S)-3-vinylpent-4-ene-2,3-diol 在 palladium on activated charcoal 、 4-甲基苯磺酸吡啶 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 、 氢气 作用下， 以 丙酮 、 苯 为溶剂， 生成 (4R,5S)-4-Ethyl-2,2,5-trimethyl-4-(R)-oxiranyl-[1,3]dioxolane
  参考文献：
  名称：

  胜木–链烯基乙二醇的无尖锐不对称环氧化：反向立体选择的起源

  摘要：

  直链和环状烯基乙二醇的Katsuki-Sharpless不对称环氧化反应得出的结论是，倒置立体选择的起源是由于乙二醇底物的两个羟基与Ti 2（酒石酸）2中的两个钛原子同时配位复杂的。

  DOI：

  10.1039/c39940002197
• 作为产物：
  描述：

  L(-)-乳酸乙酯 、 乙烯基氯化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 13.0h， 以65%的产率得到(S)-3-vinylpent-4-ene-2,3-diol
  参考文献：
  名称：

  Diastereoselective Ring-Closing Metathesis in the Synthesis of Dihydropyrans

  摘要：

  An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis based synthesis of dihydropyrans is presented in this paper. Divinyl carbinols derived from alpha-hydroxy carboxylic acid esters are elaborated to trienes with two diastereotopic vinyl moieties. Depending on the steric demand of the oxo substituent of the divinyl carbinol moiety (either unprotected OH, TBDMS, or benzyl ether) different diastereomers are preferrably formed upon ring-closing metathesis. An extension to diastereoselective double ring-closing metathesis in the formation of spirocycles has also been investigated.

  DOI：

  10.1021/jo005534x

文献信息

• A Synthesis of Densely Functionalized 2,3-Dihydropyrans Using Ring-Closing Metathesis and Base-Induced Rearrangements of Dihydropyran Oxides
  作者：Bernd Schmidt、Holger Wildemann

  DOI：10.1002/1099-0690(200009)2000:18<3145::aid-ejoc3145>3.0.co;2-b

  日期：2000.9

  presence of lithium dialkylamides to functionalized 2,3-dihydropyrans or 2,3-dihydrofurans, respectively, is described. The regiochemical outcome of the reaction can be influenced by the relative configuration of the starting epoxides and the steric demand of the base. The 2,3-dihydropyrans obtained were converted stereoselectively to difunctionalized 3,4-dihydropyrans by the carbon-Ferrier reaction, or to

  描述了二氢吡喃和二氢呋喃氧化物的制备以及它们在二烷基氨基锂存在下的重排分别为官能化的 2,3-二氢吡喃或 2,3-二氢呋喃。反应的区域化学结果会受到起始环氧化物的相对构型和碱的空间需求的影响。获得的 2,3-二氢吡喃通过碳-费里耶反应立体选择性地转化为双官能化的 3,4-二氢吡喃，或通过添加二甲酮（由硝酸铈铵介导）转化为稠合的缩醛。立体化学结果通过机械建议合理化。
• Synthesis of Functionalized 2,3- and 3,4-Dihydropyrans Starting from α-Hydroxycarboxylic Esters <i>via</i> RCM
  作者：Bernd Schmidt、Holger Wildemann

  DOI：10.1055/s-1999-2884

  日期：——

  α-Hydroxy carboxylic acids and their derivatives are naturally occurring starting materials for the synthesis of functionalized tetrahydropyrans using ring closing metathesis and base induced epoxide rearrangement as key steps. (S)-Lactic acid methyl ester has been used as the starting material for the preparation of enantiomerically pure 6-desoxy C-glycoside precursors.

  δ-羟基羧酸及其衍生物是合成官能化四氢吡喃的天然起始原料，其关键步骤是闭环偏析和碱诱导环氧化物重排。(S)-乳酸甲酯已被用作制备对映体纯度为 6-脱氧 C-糖苷前体的起始原料。
• Katsuki–Sharpless asymmetric epoxidation of alkenylethylene glycols: the origin of inverted stereoselection
  作者：Takehiko Yoshimitsu、Kunio Ogasawara

  DOI：10.1039/c39940002197

  日期：——

  The Katsuki–Sharpless asymmetric epoxidation of linear and cyclic alkenylethylene glycols has led to a conclusion that the origin of the inverted stereoselection is due to the simultaneous coordination between both hydroxy groups of the glycol substrates and both titanium atoms in the Ti2(tartrate)2 complex.

  直链和环状烯基乙二醇的Katsuki-Sharpless不对称环氧化反应得出的结论是，倒置立体选择的起源是由于乙二醇底物的两个羟基与Ti 2（酒石酸）2中的两个钛原子同时配位复杂的。
• Diastereoselective Ring-Closing Metathesis in the Synthesis of Dihydropyrans
  作者：Bernd Schmidt、Holger Wildemann

  DOI：10.1021/jo005534x

  日期：2000.9.1

  An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis based synthesis of dihydropyrans is presented in this paper. Divinyl carbinols derived from alpha-hydroxy carboxylic acid esters are elaborated to trienes with two diastereotopic vinyl moieties. Depending on the steric demand of the oxo substituent of the divinyl carbinol moiety (either unprotected OH, TBDMS, or benzyl ether) different diastereomers are preferrably formed upon ring-closing metathesis. An extension to diastereoselective double ring-closing metathesis in the formation of spirocycles has also been investigated.