3-adamantan-1-yl-but-2-enoic acid ethyl ester | 7131-19-3

• 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: 3-adamantan-1-yl-but-2-enoic acid ethyl ester
• 英文别名: (E)-ethyl 3-(adamantan-1-yl)but-2-enoate；(E)-3-(adamantan-1-yl)but-2-enoate；ethyl (E)-3-(1-adamantyl)but-2-enoate
• CAS: 7131-19-3
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: NOMATOLVDZDBHS-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-adamantan-1-yl-but-2-enoic acid ethyl ester 在 亚甲兰 lithium aluminium tetrahydride 、 氧气 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 6.5h， 生成 6-[1-(1-Adamantyl)ethenyl]spiro[1,2,4-trioxane-3,2'-adamantane]
  参考文献：
  名称：

  New Adamantane-Based Spiro 1,2,4-Trioxanes Orally Effective against Rodent and Simian Malaria

  摘要：

  New 6-arylvinyl- and 6-adamantylvinyl-substituted 1,2,4-trioxanes (13a-g and 14a,b) have been prepared and evaluated for antimalarial activity against multidrug resistant Plasmodium yoelii nigeriensis in mice by both oral and intramuscular routes. While all the 6-arylvinyl-substituted trioxanes, 13a-f, showed promising activity, none of the 6-adamantylvinyl-substituted trioxanes, 13g and 14a,b, exhibited significant activity. Trioxane, 13f, the most active compound of the series, provided 100% and 80% protection to malaria-infected mice at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively, by oral route. In this model, beta-arteether (3) provided 100% protection at 48 mg/kg x 4 days and only 20% protection at 24 mg/kg x 4 days. Trioxane 13f also showed complete suppression of parasitaemia at 10 mg/kg x 4 days by oral route in rhesus monkeys infected with P. cynomolgi. None of these trioxanes, except 13f, showed significant activity by the intramuscular route.

  DOI：

  10.1021/jm0610043
• 作为产物：
  描述：

  1-金刚烷甲酮 在 碘 、 对甲苯磺酸 、 锌 作用下， 以 苯 为溶剂， 反应 7.0h， 生成 3-adamantan-1-yl-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  New Adamantane-Based Spiro 1,2,4-Trioxanes Orally Effective against Rodent and Simian Malaria

  摘要：

  New 6-arylvinyl- and 6-adamantylvinyl-substituted 1,2,4-trioxanes (13a-g and 14a,b) have been prepared and evaluated for antimalarial activity against multidrug resistant Plasmodium yoelii nigeriensis in mice by both oral and intramuscular routes. While all the 6-arylvinyl-substituted trioxanes, 13a-f, showed promising activity, none of the 6-adamantylvinyl-substituted trioxanes, 13g and 14a,b, exhibited significant activity. Trioxane, 13f, the most active compound of the series, provided 100% and 80% protection to malaria-infected mice at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively, by oral route. In this model, beta-arteether (3) provided 100% protection at 48 mg/kg x 4 days and only 20% protection at 24 mg/kg x 4 days. Trioxane 13f also showed complete suppression of parasitaemia at 10 mg/kg x 4 days by oral route in rhesus monkeys infected with P. cynomolgi. None of these trioxanes, except 13f, showed significant activity by the intramuscular route.

  DOI：

  10.1021/jm0610043

文献信息

• Copper(<scp>i</scp>)-catalysed asymmetric allylic reductions with hydrosilanes
  作者：T. N. Thanh Nguyen、Niklas O. Thiel、Johannes F. Teichert

  DOI：10.1039/c7cc07008j

  日期：——

  copper(I)-catalysed asymmetric allylic reduction enables a regio- and stereoselective transfer of a hydride nucleophile in an SN2′-fashion onto allylic bromides. This transformation represents a conceptually orthogonal approach to allylic substitution reactions with carbon nucleophiles. A copper(I) complex based upon a chiral N-heterocyclic carbene (NHC) ligand allows for stereoselectivity reaching 99% ee

  铜（I）催化的不对称烯丙基还原可实现S N 2'形式的氢化物亲核试剂的区域和立体选择性转移到烯丙基溴上。这种转变代表了与碳亲核试剂进行烯丙基取代反应的概念上正交的方法。基于手性N-杂环卡宾（NHC）配体的铜（I）配合物可使立体选择性达到99％ee。不管起始材料的双键构型如何，该催化剂都能进行立体收敛反应。
• Diastereoselective Intramolecular Hydride Transfer Triggered by Electrophilic Halogenation of Aryl Alkenes
  作者：Bin Wang、Dhika Aditya Gandamana、David Fabian León Rayo、Fabien Gagosz、Shunsuke Chiba

  DOI：10.1021/acs.orglett.9b03548

  日期：2019.11.15

  Diastereoselective hydride transfer could be triggered by electrophilic halogenation (bromination or fluorination) of homoallylic alcohol O-Bn ethers. The resulting diastereomerically enriched haloalkyl alcohols underwent subsequent intramolecular nucleophilic substitution to afford the corresponding tetrahydrofurans.

  非对映选择性氢化物的转移可以通过均烯丙基醇O-Bn醚的亲电子卤化（溴化或氟化）来触发。所得的非对映异构体富集的卤代烷基醇随后进行分子内亲核取代，得到相应的四氢呋喃。