Ethyl (2R,3S)-2,3-epoxydecanoate | 145552-35-8

• 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: Ethyl (2R,3S)-2,3-epoxydecanoate
• 英文别名: ethyl (2R,3S)-3-heptyloxirane-2-carboxylate
• CAS: 145552-35-8
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: NDISNNKAFSHFFO-WDEREUQCSA-N

物化性质

• 沸点：
  264.6±15.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl (2R,3S)-2,3-epoxydecanoate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 13.0h， 以98%的产率得到(2S,3S)-2,3-epoxydecan-1-ol
  参考文献：
  名称：

  Total synthesis of microginin, an angiotensin-converting enzyme inhibitory pentapeptide from the blue-green alga Microcystis aeruginosa

  摘要：

  Microginin, an angiotensin-converting enzyme inhibitory peptide isolated form the blue-green alga Microcystis aeruginosa, and its three diastereoisomers were efficiently synthesized, which unequivocally established the absolute stereostructure of microginin to be 1d.

  DOI：

  10.1016/s0040-4020(01)89431-x
• 作为产物：
  描述：

  ethyl (2S,3S)-2-bromo-3-hydroxydecanoate 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以99.5%的产率得到Ethyl (2R,3S)-2,3-epoxydecanoate
  参考文献：
  名称：

  Total synthesis of microginin, an angiotensin-converting enzyme inhibitory pentapeptide from the blue-green alga Microcystis aeruginosa

  摘要：

  Microginin, an angiotensin-converting enzyme inhibitory peptide isolated form the blue-green alga Microcystis aeruginosa, and its three diastereoisomers were efficiently synthesized, which unequivocally established the absolute stereostructure of microginin to be 1d.

  DOI：

  10.1016/s0040-4020(01)89431-x

文献信息

• Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn
  作者：Kyungsoo Oh、William Eric Knabe

  DOI：10.1016/j.tet.2009.02.013

  日期：2009.4

  A mild and operationally simple deoxygenation of epoxides, sulfoxides, and amine N-oxides is described using a sub-stoichiometric amount of low-valent niobium complexes generated in situ from commercially available NbCl5 and zinc dust. The deoxygenation proceeds by a reductive cleavage of polarized O–C/O–N/O–S bonds through a single electron transfer from zinc metal to the niobium–substrate complex

  使用亚化学计量量的由市售NbCl 5和锌粉原位生成的低价铌络合物，描述了对环氧化合物，亚砜和胺N-氧化物进行温和且简单的脱氧的方法。由于铌物种的高亲氧性，单价电子从锌金属转移到铌-底物络合物，使极化的O-C / O-N / O-S键还原性裂解，从而进行脱氧。相邻的自由基稳定基团的存在对环氧底物是有利的。但是，类似的前提条件不适用于亚砜和胺N-氧化物，在这些亚胺和N-胺胺中，各种底物均能以优异的产率有效地脱氧。
• A simple route to syn α-Amino-β-Hydroxy esters by C-2 regioselective opening of a, β-Epoxy esters with metal halides
  作者：Giuliana Righi、Giovanna Rumboldt、Carlo Bonini

  DOI：10.1016/0040-4020(95)00873-7

  日期：1995.11

  α,β-Epoxy esters are opened by NaX (X = I, Br) in a regio and stereoselective fashion to β-hydroxy-α-halo esters, which represent suitable precursors of syn α-amino-β-hydroxy esters and β-hydroxy esters.

  NaX（X = I，Br）以区域和立体选择性的方式将α，β-环氧酯打开为β-羟基-α-卤代酯，β-羟基-α-卤代酯代表合成α-氨基-β-羟基酯和β-羟基酯。
• Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters
  作者：Sadao Tsuboi、Hiroyuki Furutani、Mohammad Hafeez Ansari、Takashi Sakai、Masanori Utaka、Akira Takeda

  DOI：10.1021/jo00054a036

  日期：1993.1

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.
• Total synthesis of microginin, an angiotensin-converting enzyme inhibitory pentapeptide from the blue-green alga Microcystis aeruginosa
  作者：Fumiyoshi Matsuura、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)89431-x

  日期：——

  Microginin, an angiotensin-converting enzyme inhibitory peptide isolated form the blue-green alga Microcystis aeruginosa, and its three diastereoisomers were efficiently synthesized, which unequivocally established the absolute stereostructure of microginin to be 1d.