trans-ethyl 4-mercapto-2-butenoate | 89936-85-6

• 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: trans-ethyl 4-mercapto-2-butenoate
• 英文别名: (E)-ethyl 4-mercaptobut-2-enoate；Ethyl trans-4-mercaptobutenoate；ethyl (E)-4-sulfanylbut-2-enoate
• CAS: 89936-85-6
• 化学式: C₆H₁₀O₂S
• 分子量: 146.21
• InChiKey: KCTUZVOCEAGBBQ-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  反式肉桂醛 、 trans-ethyl 4-mercapto-2-butenoate 在 (S)-diphenyl prolinol TMS ether 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以76%的产率得到(4-formyl-5-phenyl-tetrahydro-thiophen-3-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Enantioselective Organocatalytic Double Michael Addition Reactions

  摘要：

  [GRAPHICS]A novel organocatalytic, enantioselective domino double Michael addition reaction of alpha,beta-unsaturated aldehydes with ethyl 4-mercapto-2-butenoate has been developed. The process is promoted by chiral diphenylprolinol TMS ether to give chiral tetrahydrothiophenes in high to excellent levels of enantioselectivities.

  DOI：

  10.1021/ol070581y
• 作为产物：
  描述：

  4-溴巴豆酸乙酯 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 trans-ethyl 4-mercapto-2-butenoate
  参考文献：
  名称：

  A versatile synthesis of functionalized thiols

  摘要：

  The reaction of trimer 6 and an alkyl lithium afforded thiolate 7 which reacted with primary halides to produce silyl thioethers in good to excellent yields. The silyl thioethers could be hydrolyzed to the thiols using HF in acetonitrile.

  DOI：

  10.1016/s0040-4039(00)79676-6

文献信息

• Meeting Organocatalysis with Drug Discovery: Asymmetric Synthesis of 3,3′-Spirooxindoles Fused with Tetrahydrothiopyrans as Novel p53-MDM2 Inhibitors
  作者：Shengzheng Wang、Yan Jiang、Shanchao Wu、Guoqiang Dong、Zhenyuan Miao、Wannian Zhang、Chunquan Sheng

  DOI：10.1021/acs.orglett.6b00155

  日期：2016.3.4

  An organocatalytic enantioselective Michael–Michael cascade reaction is developed for the synthesis of chiral spirotetrahydrothiopyrans. This highly functionalized scaffold was assembled in moderate to good yield (55–74%) and excellent diastereo- and enantioselectivities (>30:1 dr, ≥ 99% ee) with the creation of four consecutive stereogenic centers. The novel spiro-oxindole scaffold is validated as

  已开发出一种有机催化对映选择性迈克尔-迈克尔级联反应，用于合成手性螺四氢硫吡喃。这种高度功能化的支架以中等至良好的产率（55-74％）以及出色的非对映和对映选择性（> 30：1 dr，≥99％ee）组装在一起，并创建了四个连续的立体生成中心。新型螺-羟吲哚支架被证实是一类具有良好抗肿瘤活性的新型p53-MDM2蛋白-蛋白相互作用抑制剂。
• Facile Synthesis of 3-Substituted Thiazolo[2,3-α]tetrahydroisoquinolines
  作者：Sheng-Han Huang、Wan-Yu Huang、Guo-Lun Zhang、Te-Fang Yang

  DOI：10.3390/molecules26206126

  日期：——

  It was found that 4-hydroxy-2-butenoic ester (11) could not react with 3,4-dihydro-isoquinoline (4a). Individual addition reactions of γ-mercapto-α,β-unsaturated esters (18) and -unsaturated amide (19) with 3,4-dihydroisoquinolines (4) were carried out under appropriate conditions to provide the corresponding thiazolo[2,3-α]isoquinoline derivatives with good yields (up to 87%) and significant diastereomeric

  发现4-羟基-2-丁烯酸酯(11)不能与3,4-二氢-异喹啉( 4a )反应。γ-巯基-α,β-不饱和酯（18 ）和-不饱和酰胺（19 ）与3,4-二氢异喹啉（4）的单独加成反应在适当的条件下进行，以提供相应的噻唑并[2,3-α ]异喹啉衍生物具有良好的产率（高达 87%）和显着的非对映异构选择性。讨论了关键反应的机理。
• Asymmetric Synthesis of Chiral <i>α</i> ‐CF ₂ H Spiro[Indoline‐3,3′‐Thiophene] via Phase‐Transfer Catalyzed Sulfa‐Michael/Michael Domino Reaction
  作者：Yabo Deng、Shuo Sun、Yuqiang Wang、Pengfeng Jia、Wenguang Li、Kairong Wang、Wenjin Yan

  DOI：10.1002/adsc.202101320

  日期：2022.2.15

  An asymmetric Sulfa-Michael/Michael domino reaction of (E)-4-mercapto-2-butenoates with difluoromethyl-eneoxindoles catalyzed by a quinidine-derived ammonium salts as phase transfer catalyst has been disclosed. Under mild conditions, a broad range of CF2H-containing spiro[indoline-3,3′-thiophene]s, bearing three adjacent chiral centers including two vicinal spiro quaternary stereocenters, catalysed

  已经公开了由奎尼丁衍生的铵盐作为相转移催化剂催化的( E )-4-巯基-2-丁烯酸酯与二氟甲基-烯氧吲哚的不对称磺胺-迈克尔/迈克尔多米诺反应。在温和条件下，仅由 5 mol% PTC 催化剂催化，以产率获得了范围广泛的含 CF 2 H 螺[二氢吲哚-3,3'-噻吩]，具有三个相邻的手性中心，包括两个邻位螺四元立体中心75-98%，出色的非对映选择性（在几乎所有情况下 > 20:1）和 19-98% 的对映选择性在较短的反应时间内（几乎不到 20 分钟）。
• Highly diastereoselective synthesis of spiro[tetrahydrothiophene-3,3′-pyrazol] with an all-carbon quaternary stereocenter via [3 + 2] cascade Michael/Michael cyclization catalyzed by DABCO
  作者：Guowei Cai、Shuang Liu、Jiayong Zhang、Yuanyuan Ren、He Wang、Zhiwei Miao

  DOI：10.1080/00397911.2016.1174780

  日期：2016.5.2

  ABSTRACT The diastereoselective formation of spiro[tetrahydro thiophene-3,3′-pyrazol] derivatives has been achieved via a Michael/Michael cyclization reaction. The reaction was performed using trans-ethyl 4-mercapto-2-butenoate 1 with various 4-benzylidene-5-methyl-2-phenylpyrazolones 2 catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) in toluene at 0 °C. The reaction proceeds rapidly and affords

  摘要 通过迈克尔/迈克尔环化反应实现了螺[四氢噻吩-3,3'-吡唑]衍生物的非对映选择性形成。使用 4-巯基-2-丁烯酸反式乙酯 1 与各种 4-亚苄基-5-甲基-2-苯基吡唑啉酮 2 进行反应，由 1,4-二氮杂双环 [2.2.2] 辛烷 (DABCO) 在甲苯中于 0 ℃催化℃。反应进行得很快，并以优异的产率和中等至优异的非对映选择性（高达 98% 的产率和 >20:1 dr）得到相应的螺[四氢噻吩-3,3'-吡唑]衍生物。图形概要
• Amine Thiourea Catalysed Double Michael Reaction: An Approach for the Asymmetric Synthesis of Spiro[pyrazolone-4,3′-tetrahydrothiophenes]
  作者：Alessandra Lattanzi、Sara Meninno、Jacob Overgaard

  DOI：10.1055/s-0036-1588725

  日期：——

  Dedicated to Professor Arrigo Scettri on the occasion of his 70th birthday Abstract A domino reaction, based on an organocatalysed sulfa-Michael­/Michael sequence, is demonstrated as being useful for the asymmetric synthesis of spiro[pyrazolone-4,3′-tetrahydrothiophenes] bearing three consecutive stereocentres. This new class of spirocyclic compounds has been synthesised in good yield and fairly good

  献给萨基Scettri教授在他的70之际个生日 抽象的 已证明基于有机催化的磺胺-迈克尔/迈克尔序列的多米诺反应可用于不对称合成具有三个连续立体中心的螺[吡唑啉酮-4,3'-四氢噻吩]。这种新型的螺环化合物是通过在容易获得的仲醇存在下使α，β-不饱和吡唑酮与叔丁基（E）-4-巯基-2-丁烯酸酯反应而以高收率和相当好的非对映选择性和对映选择性合成的（R，R）-1,2-二苯基乙二胺衍生的胺硫脲。 已证明基于有机催化的磺胺-迈克尔/迈克尔序列的多米诺反应可用于不对称合成具有三个连续立体中心的螺[吡唑啉酮-4,3'-四氢噻吩]。这种新型的螺环化合物是通过在容易获得的仲醇存在下使α，β-不饱和吡唑酮与叔丁基（E）-4-巯基-2-丁烯酸酯反应而以高收率和相当好的非对映选择性和对映选择性合成的（R，R）-1,2-二苯基乙二胺衍生的胺硫脲。