{2-[2-(4-hydroxyphenyl)-ethyl]-[1,3]-dithian-2-yl}-acetic acid ethyl ester | 443957-47-9

• 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: {2-[2-(4-hydroxyphenyl)-ethyl]-[1,3]-dithian-2-yl}-acetic acid ethyl ester
• 英文别名: {2-[2-(4-hydroxyphenyl)-ethyl]-[1,3]-dithian-2-yl}-ethyl acetate；Ethyl 2-[2-[2-(4-hydroxyphenyl)ethyl]-1,3-dithian-2-yl]acetate
• CAS: 443957-47-9
• 化学式: C₁₆H₂₂O₃S₂
• 分子量: 326.481
• InChiKey: RGXMYROMCBRSTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {2-[2-(4-hydroxyphenyl)-ethyl]-[1,3]-dithian-2-yl}-acetic acid ethyl ester 在 sodium tetrahydroborate 、 三乙基硼 、 三氟化硼乙醚 、 二异丁基氢化铝 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 0.08h， 生成 (+/-)-aculeatin A
  参考文献：
  名称：

  Synthesis of (±)-aculeatins A and B

  摘要：

  两种新的抗原虫和天然产物的首次合成是使用伴随的去保护二噻烷-酚氧化反应来一步形成 1,7-二氧杂二螺[5.1.5.2]十五烷核心。

  DOI：

  10.1039/b200740a
• 作为产物：
  描述：

  5-(4-benzyloxyphenyl)-3-oxopentanoic acid acid ethyl ester 在 10percentPd/C 三氟化硼乙醚 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 {2-[2-(4-hydroxyphenyl)-ethyl]-[1,3]-dithian-2-yl}-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of (±)-aculeatins A and B

  摘要：

  两种新的抗原虫和天然产物的首次合成是使用伴随的去保护二噻烷-酚氧化反应来一步形成 1,7-二氧杂二螺[5.1.5.2]十五烷核心。

  DOI：

  10.1039/b200740a

文献信息

• NOVEL POLYSPIRANE COMPOUNDS, APPLICATION THEREOF IN THE TREATMENT OF MALARIA OR TOXOPLASMOSIS AND METHOD FOR PREPARING SAME
  申请人：Wong Yung-Sing

  公开号：US20100298422A1

  公开（公告）日：2010-11-25

  Novel polyspirane compounds used in the treatment of diseases involving parasites that belong to the phylum of apicomplexae, and a method for preparing the same.

  用于治疗属于顶复门寄生虫引起的疾病的新型多螺环化合物，以及其制备方法。
• Studies towards the Synthesis of Aculeatin C
  作者：Yung-Sing Wong、Marine Peuchmaur

  DOI：10.1055/s-2007-990959

  日期：——

  Efficient activation/deprotection reactions of functional groups by PIFA reagent allowed for the construction of the polyspirocyclic core of aculeatin C according to a new polyspiro annulation approach. Addition of TFA increased the yield and the selectivity to the benefit of the desired conformer.

  利用 PIFA 试剂对官能团进行高效的活化/脱保护反应，可以根据一种新的多螺环化方法构建出 aculeatin C 的多螺环核心。加入反式脂肪酸提高了产率和选择性，有利于获得所需的构象。
• Polyol Synthesis with β-Oxyanionic Alkyllithium Reagents: Syntheses of Aculeatins A, B, and D
  作者：Viengkham Malathong、Scott D. Rychnovsky

  DOI：10.1021/ol901623h

  日期：2009.9.17

  route was developed. The β-phenylthio alcohols were prepared from optically pure oxiranes. Deprotonation and reductive lithiation generated the key intermediate, a β-oxyanionic alkyllithium reagent. Addition to a Weinreb amide produced the β-hydroxy ketone in >90% yield using only 1.5 equiv of the phenylthio alcohol. Stereoselective reduction of the ketone led to either the syn- or anti-1,3-diol. This simple

  开发了使用非羟醛路线合成酮羟醛产品。β-苯硫醇由光学纯环氧乙烷制备。去质子化和还原锂化产生了关键中间体，β-氧阴离子烷基锂试剂。添加到 Weinreb 酰胺中，仅使用 1.5 当量的苯硫醇即可以 >90% 的收率产生 β-羟基酮。酮的立体选择性还原导致合成-或反-1,3-二醇。这个简单的收敛序列用于从一个常见的中间体制备 aculeatins A、B 和 D。
• Hypervalent iodine(III)-mediated tandem oxidative reactions: application for the synthesis of bioactive polyspirocyclohexa-2,5-dienones
  作者：Mariam Traoré、Soumeth Ahmed-Ali、Marine Peuchmaur、Yung-Sing Wong

  DOI：10.1016/j.tet.2010.04.135

  日期：2010.7

  In 2002, we reported the first total syntheses of potent antimalarial natural products, the aculeatins, employing the concept of tandem oxidative reactions mediated by hypervalent iodine(III) reagent to access to polyspirocyclohexa-2,5-dienone cores in very concise manner. Efforts in this field have allowed to identify cyclohexa-2,5-dienone group as a new potent class of pharmacophoric group for treating malaria disease. This article sums up recent contributions devoted to the synthesis of complex and diverse polycyclic structures using the concept of tandem oxidative activations, with p-phenol as co-reactant. More recently, we have explored a variant of the new tandem oxidative reactions that employs a catalytic amount of 4-iodotoluene in the presence of mCPBA as the stoichiometric oxidant (Kita's procedure). (C) 2010 Elsevier Ltd. All rights reserved.
• Enhanced Antimalarial Activity of Novel Synthetic Aculeatin Derivatives
  作者：Marine Peuchmaur、Nadia Saïdani、Cyrille Botté、Eric Maréchal、Henri Vial、Yung-Sing Wong

  DOI：10.1021/jm8007322

  日期：2008.8.1

  We report the design, synthesis, and in vitro evaluation of novel polyspirocyclic structures, inspired by the antimalarial natural products, the aculeatins. A divergent synthetic strategy was conceived for the practical supply and has allowed the discovery of two novel and more potent analogues active on the Plasmodium falciparum 3D7 strain. Moreover, these compounds proved to be potent against Toxoplasma gondii. A number Of features that govern these inhibitions were identified.