(2S^*,3S^*,6Z)-2,3-Epoxy-6-nonen-1-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S^*,3S^*,6Z)-2,3-Epoxy-6-nonen-1-ol
• 英文别名: [(2S,3S)-3-[(Z)-hex-3-enyl]oxiran-2-yl]methanol
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: MQDJFUJCJSWIEY-HIYAPSCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S^*,3S^*,6Z)-2,3-Epoxy-6-nonen-1-ol 在 lithium iodide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 7.0h， 以67%的产率得到(2R*,3R*,6Z)-1-Iodo-6-nonen-2,3-diol
  参考文献：
  名称：

  C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide

  摘要：

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.

  DOI：

  10.1021/jo00120a025
• 作为产物：
  描述：

  反-2,顺6-壬二烯醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 生成 (2S^*,3S^*,6Z)-2,3-Epoxy-6-nonen-1-ol
  参考文献：
  名称：

  乙酸铅（IV）介导的β-羟基醚的裂解：α-乙酰氧基羰基化合物的对映选择性合成

  摘要：

  通过用四乙酸铅处理2，3-环氧伯醇可以有效地合成α-乙酰氧基醛或α-乙酰氧基酮。以完全的区域和立体选择性进行的反应有助于通过Sharpless环氧化由烯丙醇对映体选择性合成α-乙酰氧基羰基化合物。具有氧化的五元，六元或七元环的环状β-羟基醚被转化为α-乙酰氧基醚。

  DOI：

  10.1016/j.tet.2011.09.056

文献信息

• A new unusual C-1 substitution of 2,3 epoxy alcohols with LiI: regio and stereoselective obtaining of 1-iodo 2,3 diols and 2,3-diols
  作者：Carlo Bonini、Claudio Giuliano、Giuliana Righi、Leucio Rossi

  DOI：10.1016/s0040-4039(00)60207-1

  日期：1992.11

  2,3 epoxy alcohols ( and ) underwent an unusual substitution at C-1, with the use of excess LiI at 70°, affording the corresponding 1-iodo-2,3 diols. Starting with (E) 2,3 epoxy alcohols the stereochemistry of the final diols was demonstrated to be ; a possible mechanism, based on some experimental data, is also showed.

  2,3环氧醇（和）在C-1处进行了不寻常的取代，在70°下使用了过量的LiI，得到了相应的1-io-2,3二醇。从（E）2,3环氧醇开始，最终二醇的立体化学被证明是：根据一些实验数据，还显示了一种可能的机制。
• Regioselective opening of epoxy alcohols: mild chemo- and stereoselective preparation of iodohydrins and 1,2-diols
  作者：Carlo Bonini、Giuliana Righi、Giovanni Sotgiu

  DOI：10.1021/jo00021a045

  日期：1991.10

  Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.