ethyl 2,3-dihydroxyoctanoate | 136031-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-dihydroxyoctanoate
• 英文别名: (2R,3S)-ethyl 2,3-dihydroxyoctanoate；ethyl (2R,3S)-dihydroxyoctanoate；ethyl (2R,3S)-2,3-dihydroxyoctanoate
• CAS: 136031-99-7
• 化学式: C₁₀H₂₀O₄
• 分子量: 204.266
• InChiKey: ZDLCOYBBKZUYJJ-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-dihydroxyoctanoate 在 咪唑 、 4-二甲氨基吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 二正丁基氧化锡 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (5S,6S)-6-(tert-butyldimethylsilyloxy)undec-1-en-5-ol
  参考文献：
  名称：

  Enantioselective synthesis of C1-C4 and C5-C14 fragments of cytospolide D

  摘要：

  DOI：

  10.24820/ark.5550190.p011.648
• 作为产物：
  描述：

  反式-2-辛烯酸乙酯 在 AD-mix-α 作用下， 以98%的产率得到ethyl 2,3-dihydroxyoctanoate
  参考文献：
  名称：

  A concise synthesis of pinellic acid using a cross-metathesis approach

  摘要：

  A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. This synthesis is the shortest to date, furnishing pinellic acid in 17% overall yield via only seven steps from a readily available known dihydroxy ester. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.063

文献信息

• Dihydroxylation of Olefins with Potassium Permanganate Catalyzed­ by Imidazolium Salt
  作者：Zhi-Bin Luo、Ji-Min Xie、Imran Khan、Anil Valeru、Yin Xu、Bin Liu、Bhavanarushi Sangepu

  DOI：10.1055/s-0036-1591763

  日期：2018.5

  cost-effective cis-di­hydroxylation reaction of acrylate derivatives was achieved. The reaction proceeded in acetone with an imidazolium salt as catalyst to furnish the dihydroxylation of olefins at 0–5 °C using KMnO4 as the oxidant. This efficient and non-aqueous protocol was highly suitable for the large-scale preparation of cis-dihydroxylated compounds from the corresponding acrylate derivatives

  摘要 实现了丙烯酸酯衍生物的有效和成本有效的顺式-二羟基化反应的开发。反应在丙酮中以咪唑鎓盐为催化剂进行，使用KMnO 4作为氧化剂在0–5°C的条件下进行烯烃的二羟基化。这种有效且非水的方案非常适合以高收率从相应的丙烯酸酯衍生物大规模制备顺式-二羟基化化合物，而不会发生过氧化。 实现了丙烯酸酯衍生物的有效和成本有效的顺式-二羟基化反应的开发。反应在丙酮中以咪唑鎓盐为催化剂进行，使用KMnO 4作为氧化剂在0–5°C的条件下进行烯烃的二羟基化。这种有效且非水的方案非常适合以高收率从相应的丙烯酸酯衍生物大规模制备顺式-二羟基化化合物，而不会发生过氧化。
• Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation
  作者：Pietro Allevi、Giorgio Tarocco、Alessandra Longo、Mario Anastasia、Francesco Cajone

  DOI：10.1016/s0957-4166(97)00125-0

  日期：1997.4

  The enantioselective synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product formed in peroxidised liver microsomal lipids, is accomplished via a Sharpless AD reaction alone or associated as appropriate with a regioselective epimerisation of one of the introduced hydroxy groups. (C) 1997 Elsevier Science Ltd.
• The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement
  作者：K. Barry Sharpless、Willi Amberg、Youssef L. Bennani、Gerard A. Crispino、Jens Hartung、Kyu Sung Jeong、Hoi Lun Kwong、Kouhei Morikawa、Zhi Min Wang

  DOI：10.1021/jo00036a003

  日期：1992.5

  Two key improvements in the osmium-catalyzed asymmetric dihydroxylation have l
• KIM, B. MOON;SHARPLESS, K. BARRY, TETRAHEDRON LETT., 31,(1990) N0, C. 4317-4320
  作者：KIM, B. MOON、SHARPLESS, K. BARRY

  DOI：——

  日期：——
• A concise synthesis of pinellic acid using a cross-metathesis approach
  作者：Ayako Miura、Shigefumi Kuwahara

  DOI：10.1016/j.tet.2009.02.063

  日期：2009.4

  A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. This synthesis is the shortest to date, furnishing pinellic acid in 17% overall yield via only seven steps from a readily available known dihydroxy ester. (C) 2009 Elsevier Ltd. All rights reserved.