ethyl 2-hydroxyhept-6-enoate | 201539-51-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-hydroxyhept-6-enoate
• CAS: 201539-51-7
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: JFOXBMYJIWOVOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxyhept-6-enoate 在 吡啶 、 nickel(II) iodide 、 4-二甲氨基吡啶 、 2-(4,5-二氢-1H-咪唑-2-基)-吡啶 、 三乙胺 、 magnesium chloride 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 生成 methyl 4-(1-cyclopentyl-2-ethoxy-2-oxoethyl)benzoate
  参考文献：
  名称：

  Ni-Catalyzed Reductive C–O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides

  摘要：

  A Ni-catalyzed reductive cross-coupling of alpha-hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes alpha-aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron withdrawing and-donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates alpha-carbonyl radicals.

  DOI：

  10.1021/acs.orglett.9b00174
• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 5.0h， 生成 ethyl 2-hydroxyhept-6-enoate
  参考文献：
  名称：

  不饱和α-羟基酸的对映选择性合成

  摘要：

  （S）和（R）-2-羟基己5-烯酸以及（S）-和（R）-2-羟基庚6-烯酸以优异的收率和对映体过量（> 99％ee）制备酶催化酯的水解并在单锅法中还原酮，从而生成相应的α-酮酯。（S）-2-羟基戊-4-烯酸的对映选择性合成是通过使烯丙基溴和铟金属衍生的试剂与水合草酸8-苯基薄荷基乙二酸酯的水合物反应而实现的。

  DOI：

  10.1016/s0957-4166(97)00571-5

文献信息

• FeCl₃-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans
  作者：Amandine Guérinot、Anna Serra-Muns、Christian Gnamm、Charlélie Bensoussan、Sébastien Reymond、Janine Cossy

  DOI：10.1021/ol100422d

  日期：2010.4.16

  The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.
• FeCl3·6H2O-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives
  作者：Amandine Guérinot、Anna Serra-Muns、Charlélie Bensoussan、Sébastien Reymond、Janine Cossy

  DOI：10.1016/j.tet.2011.03.112

  日期：2011.7

  A highly diastereoselective iron-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from zeta-hydroxy allylic derivatives is described. The FeCl3 center dot 6H(2)O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high diastereoselectivities observed. (C) 2011 Elsevier Ltd. All rights reserved.
• Iodocyclisation studies on unsaturated α-hydroxy esters
  作者：Jacqueline A. Macritchie、Torren M. Peakman、Alan Silcock、Christine L. Willis

  DOI：10.1016/s0040-4039(98)01611-6

  日期：1998.10

  Iodocyclisation of ethyl 2-hydroxyhex-5-enoate 1 and the homologous hept-6-enoate 4 under thermodynamic or kinetic conditions gave the novel tetrahydrofurans 2/3 and tetrahydropyrans 5/6 respectively. In contrast, ethyl 2-hydroxypent-4-enoate 7 gave iodolactones 9 and 10 in good yield, rather than the expected cyclic ether 8. Oxygen-18 studies revealed that the mechanism of iodolactonisation of 7 is dependent upon the reaction conditions employed. (C) 1998 Elsevier Science Ltd. Ail rights reserved.