ethyl 6-(tetrahydro-2H-pyran-2-yloxy)-2-hexynoate | 131271-33-5

• 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 6-(tetrahydro-2H-pyran-2-yloxy)-2-hexynoate
• 英文别名: Ethyl 6-(oxan-2-yloxy)hex-2-ynoate；ethyl 6-(oxan-2-yloxy)hex-2-ynoate
• CAS: 131271-33-5
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: GBRONSQHMWYMLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-(tetrahydro-2H-pyran-2-yloxy)-2-hexynoate 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以72%的产率得到ethyl 6-hydroxyhex-2-ynoate
  参考文献：
  名称：

  Discovery of Orally Available 8-Aza-5-thiaProstaglandin E1 Analogs as Highly Selective EP4 Agonists

  摘要：

  合成了 8-aza-16-aryl 前列腺素 E1 (PGE1) 和 8-aza-5-thia-16-arylPGE1 类似物，并对它们的亚型受体亲和力和 EP4 激动剂活性进行了评估，以确定具有口服疗效的亚型选择性 EP4 激动剂。通过抑制大鼠体内脂多糖（LPS）诱导的肿瘤坏死因子（TNF）-α的产生，对代表性化合物的药代动力学特征和体内疗效进行了评估。对结构-活性关系（SARs）进行了表征和展示。与之前报道的类似物 2a 相比，在测试的化合物中，有几种显示出更好的口服暴露和/或体内疗效。

  DOI：

  10.1248/cpb.59.1523
• 作为产物：
  描述：

  4-戊炔-1-醇 在 乙基溴化镁 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 ethyl 6-(tetrahydro-2H-pyran-2-yloxy)-2-hexynoate
  参考文献：
  名称：

  镍配合物合成环状硫化物催化不饱和硫代乙酸盐和硫代磺酸盐的电还原

  摘要：

  通过不稳定的硫醇的闭环合成具有四到六元环的官能化的环硫化物，所述不稳定的硫醇是通过镍络合物催化的具有适当放置的亲电烯烃或乙炔的硫代乙酸盐和硫代磺酸盐的电还原而原位形成的。

  DOI：

  10.1016/s0040-4039(98)01802-4

文献信息

• Synthesis of cyclic sulfides by nickel complexes catalyzed electroreduction of unsaturated thioacetates and thiosulfonates
  作者：Shigeko Ozaki、Eiki Matsui、Toyokazu Saiki、Hideaki Yoshinaga、Hidenobu Ohmori

  DOI：10.1016/s0040-4039(98)01802-4

  日期：1998.10

  Functionalized cyclic sulfides with four to six membered rings were synthesized by ring closure of the labile thiols which were formed in situ by the nickel complex catalyzed electroreduction of the thioacetates and thiosulfonates having suitably placed electrophilic olefins or acetylenes.

  通过不稳定的硫醇的闭环合成具有四到六元环的官能化的环硫化物，所述不稳定的硫醇是通过镍络合物催化的具有适当放置的亲电烯烃或乙炔的硫代乙酸盐和硫代磺酸盐的电还原而原位形成的。
• A new methodology to key intermediates for synthesizing polyene compounds
  作者：Dawei Ma、Xiyan Lu

  DOI：10.1016/s0040-4020(01)96004-1

  日期：1990.1
• Phosphine-Catalyzed <i>Anti</i>-Hydroboration of Internal Alkynes
  作者：Kazunori Nagao、Ayaka Yamazaki、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/acs.orglett.8b00390

  日期：2018.4.6

  Trialkylphosphine organocatalysts have enabled regioselective anti-hydroboration of internal, alkynes with pinacolborane reagents to provide (E)-disubstituted alkenylboronate compounds. The alkenyl-boronate can be used for derivatizations, such as protodeborylation, Suzuld-Miyaura coupling, conjugate reduction, and Diels-Alder reactions.
• <i>Anti</i>-Selective Vicinal Silaboration and Diboration of Alkynoates through Phosphine Organocatalysis
  作者：Kazunori Nagao、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/acs.orglett.5b00305

  日期：2015.3.6

  Trialkylphosphine organocatalysts have enabled anti-selective vicinal silaboration and diboration of the C-C triple bond in alkynoates to produce beta-boryl-alpha-silyl acrylates and alpha,beta-diboryl acrylates, respectively. The anti stereoselectivity was complete and robust. A variety of functional groups were tolerated in the alkynoates. The two vicinally installed heteroatom substituents of the beta-boryl-alpha-silyl acrylates and alpha,beta-diboryl acrylates could be differentiated and transformed in a stepwise manner, allowing the synthesis of a diverse array of unsymmetrical tetrasubstituted alkenes.
• Discovery of Orally Available 8-Aza-5-thiaProstaglandin E1 Analogs as Highly Selective EP4 Agonists
  作者：Tohru Kambe、Toru Maruyama、Masayuki Nakano、Yoshiyuki Yamaura、Tomoyuki Shono、Akiteru Seki、Kiyoto Sakata、Takayuki Maruyama、Hisao Nakai、Masaaki Toda

  DOI：10.1248/cpb.59.1523

  日期：——

  Analogs 8-aza-16-aryl prostaglandin E1 (PGE1) and 8-aza-5-thia-16-arylPGE1 were synthesized and evaluated with respect to their subtype receptor affinity and EP4 agonist activity for the purposes of identifying subtype-selective EP4 agonists that demonstrate oral efficacy. Using an inhibition assay of lipopolysaccharide (LPS)-induced tumor necrosis factor (TNF)-α production in rats, representative compounds were evaluated for their pharmacokinetic profiles and in vivo efficacy. Structure–activity relationships (SARs) were characterized and presented. Of the compounds tested, several demonstrated better oral exposure and/or in vivo efficacy compared with the previously reported analog 2a.

  合成了 8-aza-16-aryl 前列腺素 E1 (PGE1) 和 8-aza-5-thia-16-arylPGE1 类似物，并对它们的亚型受体亲和力和 EP4 激动剂活性进行了评估，以确定具有口服疗效的亚型选择性 EP4 激动剂。通过抑制大鼠体内脂多糖（LPS）诱导的肿瘤坏死因子（TNF）-α的产生，对代表性化合物的药代动力学特征和体内疗效进行了评估。对结构-活性关系（SARs）进行了表征和展示。与之前报道的类似物 2a 相比，在测试的化合物中，有几种显示出更好的口服暴露和/或体内疗效。