2-thiophene acetic acid vinyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-thiophene acetic acid vinyl ester
• 英文别名: Vinyl thiolacetate；ethenyl 2-thiophen-2-ylacetate
• 化学式: C₈H₈O₂S
• 分子量: 168.216
• InChiKey: IFMUNEPYWVGZCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  阿霉素 、 2-thiophene acetic acid vinyl ester 在 subtilisin Carlsberg protease ion-paired with Aerosol OT 作用下， 以94%的产率得到14-thiophene-2-ylmethyl-Doxorubicin ester
  参考文献：
  名称：

  新型细胞毒性阿霉素衍生物的非水生物催化合成：利用盐活化和增溶枯草杆菌蛋白酶区域选择性的意外差异

  摘要：

  两种酶，毛毛虫脂肪酶和枯草杆菌蛋白酶 Carlsberg (SC)，催化阿霉素 (DOX) 的非水酰化。与未处理的酶相比，甲苯中丁酸乙烯酯在 C-14 位的 DOX 酰化率通过与气溶胶 OT (AOT) 离子配对的脂肪酶高 25 倍，由 98% (w /w) KCl 共冻干（分别为 3.21 和 0.67 μmol/min g-脂肪酶，相对于 0.13 μmol/min g-脂肪酶）。颗粒枯草杆菌蛋白酶 (SC) 几乎不能进行 DOX 酰化，但离子对 SC (AOT-SC) 以 2.85 μmol/min g-蛋白酶的速率催化酰化。M. javanicus 制剂、AOT-SC 和 SC 专门酰化 DOX 的 C14 伯羟基。SC 与 98% (w/w) KCl 的共冻干扩大了酶的区域特异性，使得 KCl-SC 额外酰化了 C4' 羟基和 C3' 胺基团。使用 KCl-SC 的 DOX 总转化率为

  DOI：

  10.1021/ja015977y

文献信息

• Asymmetric Coupling of Carbon‐Centered Radicals Adjacent to Nitrogen: Copper‐Catalyzed Cyanation and Etherification of Enamides
  作者：Guoyu Zhang、Song Zhou、Liang Fu、Pinhong Chen、Yibiao Li、Jianping Zou、Guosheng Liu

  DOI：10.1002/anie.202008338

  日期：2020.11.9

  The first copper‐catalyzed asymmetric cyanation and etherification reactions of enamides have been established, where a carbon‐centered radical adjacent to a nitrogen atom (CRAN) is enantioselectively trapped by a chiral copper(II) species. Moreover, the asymmetric cyanation of vinyl esters was disclosed as well. These reactions feature very mild reaction conditions and high functional group tolerance

  已经建立了第一个铜催化的酰胺类不对称氰化和醚化反应，其中与氮原子（CRAN）相邻的碳中心自由基被手性铜（II）物种对映选择性地捕获。此外，还公开了乙烯基酯的不对称氰化。这些反应具有非常温和的反应条件和较高的官能团耐受性，并提供了一系列手性的α-氰基酰胺，α-氰基酯和α-半胱氨酸，收率高，对映选择性优异。手性α-氰基酰胺很容易转化为对映体富集的1,2-二胺和氨基酸。
• [EN] METHODS FOR PREPARING DOXORUBICIN DERIVATIVES<br/>[FR] PROCEDES PERMETTANT DE PREPARER DES DERIVES DE DOXORUBICINE
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2003057687A1

  公开（公告）日：2003-07-17

  The present invetion relates to a process for preparation of a product compound of formula (I), where R1 is an acyl group. The process involves reacting a starting compound of formula (II), with an activated acyl donor compound in the presence of a non-chemically modified lipase, under conditions effective to produce the product compound.
• [EN] METHODS FOR PREPARING ANTHRACYCLINONE DERIVATIVES AND ANTHRACYCLINONE DERIVATIVES PER SE<br/>[FR] METHODES PERMETTANT DE PREPARER DES DERIVES D'ANTHRACYCLINONE ET LESDITS DERIVES D'ANTHRACYCLINONE
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2003057896A1

  公开（公告）日：2003-07-17

  The present invention relates to a process for preparation of a product compound of the Formula (I), where R1 is an acyl group, R2 is H, an N-alkylated amino sugar, or a non-basic sugar moiety, and R3 is H, OH, or OCH3. The process involves reacting a starting compound of the Formula (II) with an acyl donor compound in the presence of a non-chemically modified lipase, under conditions effective to produce the product compound. Another aspect of the present invention relates to a compound of the following Formula (III), where: R1 is an acyl radical of a carboxylic acid selected from the group consisting of: polyethylene glycol acetic acid and polyunsaturated fatty acid; and R2 = 2,6-dideoxy-2-fluoro-α-talopyranosyl; 3-trifluoroacetylamino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl; or 3-deamino-3-(2'-pyrroline-1'-yl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl; or a pharmaceutically acceptable salt thereof. The present invention also relates to a compound of the Formula (IV) where n is 4 or 5, or a pharmaceutically acceptable salt thereof. Another aspect of the present invention relates to a compound of the Formula (V) where: R1 is an acyl group, R2 is 3-substituted allyloxycarbonylamino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl, R3 is H, OH, or OCH3.
• [EN] BIOCATALYTIC PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED PRAMIPEXOLE<br/>[FR] PROCEDE BIOCATALYTIQUE DE FABRICATION DE PRAMIPEXOLE ENRICHI ENANTIOMERIQUEMENT
  申请人：AMR TECHNOLOGY INC

  公开号：WO2006012277A2

  公开（公告）日：2006-02-02

  biocatalytic process for preparing enantiomerically enriched pramipexole and pramipexole precursors are disclosed.
• Nonaqueous Biocatalytic Synthesis of New Cytotoxic Doxorubicin Derivatives:  Exploiting Unexpected Differences in the Regioselectivity of Salt-Activated and Solubilized Subtilisin
  作者：David H. Altreuter、Jonathan S. Dordick、Douglas S. Clark

  DOI：10.1021/ja015977y

  日期：2002.3.1

  a salt-activated enzyme. Using AOT-SC catalysis, four unique selectively acylated DOX analogues were generated, and KCl-SC was used to prepare DOX derivatives acylated at the alternative sites. Cytotoxicities of select derivatives were evaluated against the MCF7 breast cancer cell line (DOX IC50 = 27 nM) and its multidrug-resistant sub-line, MCF7-ADR (DOX IC50 = 27 muM). The novel derivative 14-(2-thiophene

  两种酶，毛毛虫脂肪酶和枯草杆菌蛋白酶 Carlsberg (SC)，催化阿霉素 (DOX) 的非水酰化。与未处理的酶相比，甲苯中丁酸乙烯酯在 C-14 位的 DOX 酰化率通过与气溶胶 OT (AOT) 离子配对的脂肪酶高 25 倍，由 98% (w /w) KCl 共冻干（分别为 3.21 和 0.67 μmol/min g-脂肪酶，相对于 0.13 μmol/min g-脂肪酶）。颗粒枯草杆菌蛋白酶 (SC) 几乎不能进行 DOX 酰化，但离子对 SC (AOT-SC) 以 2.85 μmol/min g-蛋白酶的速率催化酰化。M. javanicus 制剂、AOT-SC 和 SC 专门酰化 DOX 的 C14 伯羟基。SC 与 98% (w/w) KCl 的共冻干扩大了酶的区域特异性，使得 KCl-SC 额外酰化了 C4' 羟基和 C3' 胺基团。使用 KCl-SC 的 DOX 总转化率为