ethyl 2-[2-(4-fluorophenyl)-2-oxoethyl]sulfanylacetate | 1152629-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-[2-(4-fluorophenyl)-2-oxoethyl]sulfanylacetate
• 英文别名: ethyl 2-((2-(4-fluorophenyl)-2-oxoethyl)thio)acetate
• CAS: 1152629-06-5
• 化学式: C₁₂H₁₃FO₃S
• mdl: MFCD12493879
• 分子量: 256.298
• InChiKey: XCGYYDQKHJXVFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  362.7±32.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[2-(4-fluorophenyl)-2-oxoethyl]sulfanylacetate 在 N-甲基吗啉 、 titanium(IV) isopropylate 、 甲酸 、 N,O-双三甲硅基乙酰胺 、 水 、 四氯化钛 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 对甲苯磺酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium chloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 154.5h， 生成 (3R,4R)-1-(4-fluorophenyl)-3-[(4-fluorobenzoyl)methylthio]-4-{4-[N-(carboxymethyl)carbamoylmethoxy]phenyl}azetidin-2-one
  参考文献：
  名称：

  Selection and Development of a Route for Cholesterol Absorption Inhibitor AZD4121

  摘要：

  The development of a synthetic route to the cholesterol absorption inhibitor AZD4121 is presented. Key steps are a highly enantioselective CBS reduction, a stereospecific Staudinger reaction, an amine/lithium chloride mediated ester hydrolysis, and a resolution of a 50:50 diastereomeric mixture by recrystallization. The synthesis was accomplished in 10 linear steps, and the overall yield, when compared with the lead optimization (LO) route, was improved from 1% to 20%. All purifications of intermediates through preparative HPLC or silica gel chromatography were avoided. This was possible since many of the intermediates along the route could be used as such in the next step until an intermediate with suitable crystalline properties could be identified and purified through crystallization.

  DOI：

  10.1021/op200314z
• 作为产物：
  描述：

  2-溴-4'-氟苯乙酮 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 ethyl 2-[2-(4-fluorophenyl)-2-oxoethyl]sulfanylacetate
  参考文献：
  名称：

  使用芳烃的Uxpol-Oxa- [2,3]嗜向性重排反应，用于功能化烯醇醚的合成

  摘要：

  据报道涉及芳烃的oxa- [2,3]σ重排以酮为主体，其中的C═O键极性相反。β-酮硫醚和芳烃在原位生成的硫烷基化物经过有效的重排，可以轻松，稳健地合成高官能度的烯醇醚，并具有出色的官能团相容性。初步的机理研究排除了在这种情况下运行Pummerer型重排的可能性。

  DOI：

  10.1021/acs.orglett.1c00911

文献信息

• WO2020131807A5
  申请人：——

  公开号：WO2020131807A5

  公开（公告）日：2022-12-23
• INHIBITORS OF APOL1 AND METHODS OF USING SAME
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：EP3897833A1

  公开（公告）日：2021-10-27
• [EN] INHIBITORS OF APOL1 AND METHODS OF USING SAME<br/>[FR] INHIBITEURS D'APOL1 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：VERTEX PHARMA

  公开号：WO2020131807A1

  公开（公告）日：2020-06-25

  The disclosure provides at least one entity chosen from compounds of formula (I), solid state forms of the same, compositions comprising the same, and methods of using the same, including use in treating focal segmental glomerulosclerosis (FSGS) and/or non-diabetic kidney disease (NDKD).
• An Umpolung Oxa-[2,3] Sigmatropic Rearrangement Employing Arynes for the Synthesis of Functionalized Enol Ethers
  作者：Rahul N. Gaykar、Malini George、Avishek Guin、Subrata Bhattacharjee、Akkattu T. Biju

  DOI：10.1021/acs.orglett.1c00911

  日期：2021.5.7

  An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C═O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic

  据报道涉及芳烃的oxa- [2,3]σ重排以酮为主体，其中的C═O键极性相反。β-酮硫醚和芳烃在原位生成的硫烷基化物经过有效的重排，可以轻松，稳健地合成高官能度的烯醇醚，并具有出色的官能团相容性。初步的机理研究排除了在这种情况下运行Pummerer型重排的可能性。
• Selection and Development of a Route for Cholesterol Absorption Inhibitor AZD4121
  作者：Staffan Karlsson、J. Henrik Sörensen

  DOI：10.1021/op200314z

  日期：2012.4.20

  The development of a synthetic route to the cholesterol absorption inhibitor AZD4121 is presented. Key steps are a highly enantioselective CBS reduction, a stereospecific Staudinger reaction, an amine/lithium chloride mediated ester hydrolysis, and a resolution of a 50:50 diastereomeric mixture by recrystallization. The synthesis was accomplished in 10 linear steps, and the overall yield, when compared with the lead optimization (LO) route, was improved from 1% to 20%. All purifications of intermediates through preparative HPLC or silica gel chromatography were avoided. This was possible since many of the intermediates along the route could be used as such in the next step until an intermediate with suitable crystalline properties could be identified and purified through crystallization.