(E)-3-(甲硫基)丙烯酸 | 26398-93-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-3-(甲硫基)丙烯酸
• 英文名称: (E)-3-(methylthio)acrylic acid
• 英文别名: (E)-3-(methylthio)-propenoic acid；trans-3-(Methylthio)-acrylsaeure；3-(Methylthio)acrylic acid, (E)-；(E)-3-methylsulfanylprop-2-enoic acid
• CAS: 26398-93-6
• 化学式: C₄H₆O₂S
• 分子量: 118.156
• InChiKey: RCZLOQQOUWHMIS-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(甲硫基)丙烯酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (E)-3-methylsulfanylprop-2-enoyl chloride
  参考文献：
  名称：

  Synthesis and structure elucidation of open-chained putrescine-bisamides from Aglaia species

  摘要：

  The structures of the eight recently described open-chained putrescine bisamide alkaloids secoodorine (1), aglaithioduline (3), aglaiduline (4), aglaidithioduline (5), grandiamide B (13), grandiamide C (14), pyramidatine (20), and secopiriferine (22), which were isolated from different Aglaia species, have been verified by synthesis. In addition to that, the published structure 2 for hemileptagline had to be revised, and for secoodorine (1) the absolute configuration could be established. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00751-2
• 作为产物：
  描述：

  3-(methylthio)acrylic acid 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 (E)-3-(甲硫基)丙烯酸
  参考文献：
  名称：

  Total synthesis and biological evaluation of methylgerambullone

  摘要：

  First total synthesis of methylgerambullone (MGB, 1) isolated from Glycosmis angustifolia was completed via a convergent route. The effect of MGB on the contractile responses of the isolated guinea-pig ileum induced by acetylcholine was investigated. As a result, it showed a potent relaxation rate (78.66 +/- 4.30% at 100 mg/L) in a concentration-dependent manner on longitudinal smooth muscle contraction of isolated guinea-pig ileum induced by 1 mu M acetylcholine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.040

文献信息

• N‐Methylated Peptide Synthesis via Generation of an Acyl N‐Methylimidazolium Cation Accelerated by a Brønsted Acid
  作者：Yuma Otake、Yusuke Shibata、Yoshihiro Hayashi、Susumu Kawauchi、Hiroyuki Nakamura、Shinichiro Fuse

  DOI：10.1002/anie.202002106

  日期：2020.7.27

  formation remains a critical aspect of N‐methylated peptide synthesis. In this study, we synthesized a variety of dipeptides in high yields, without severe racemization, from equivalent amounts of amino acids. Highly reactive N‐methylimidazolium cation species were generated in situ to accelerate the amidation. The key to success was the addition of a strong Brønsted acid. The developed amidation enabled

  牢固的酰胺键形成的发展仍然是N-甲基化肽合成的关键方面。在这项研究中，我们从等量的氨基酸中高收率合成了各种二肽，而没有严重的消旋作用。高反应性的N-甲基咪唑鎓阳离子原位生成以加速酰胺化反应。成功的关键是加入强力的布朗斯台德酸。与常规酰胺化的结果相比，开发的酰胺化使得能够在较短的时间内以较高的产率合成大体积的肽。另外，可以通过使用微流反应器或常规烧瓶来进行酰胺化。天然存在的大体积N-甲基化肽，蝶酰胺I-IV的首次全合成。根据实验结果和理论计算，
• Synthesis and effects of 3-methylthiopropanoyl thiolesters of lipoic acid, methional metabolite mimics
  作者：Celine Courvoisier、Marie Julie Paret、Jacqueline Chantepie、Jacques Goré、Guy Fournet、Gerard Quash

  DOI：10.1016/j.bioorg.2005.11.001

  日期：2006.2

  8S-Bis(3-methylthiopropanoyl) thiolesters of lipoic acid were synthesized with the carboxyl moiety of lipoate modified as methyl or water soluble choline esters. Evaluation on different cell lines in culture showed that they possessed modest antiproliferative activity. However, the 6-fold decrease in IC50 (from 270 to 45 microM) observed with the water soluble 6S,8S-bis(3-methylthiopropenoyl) thiolester dehydro derivative

  合成了硫辛酸的6S，8S-双（3-甲基硫代丙酰基）硫醇酯，并将硫辛酸酯的羧基部分修饰为甲基或水溶性胆碱酯。对培养物中不同细胞系的评估表明它们具有适度的抗增殖活性。然而，在人上皮前列腺癌细胞系（DU145）上使用水溶性6S，8S-双（3-甲基硫代丙烯酰基）硫代酯脱水衍生物观察到的IC50降低了6倍（从270降至45 microM），主张3 -甲硫基丙酰基代谢物，是衍生自蛋氨酸的内源性生长调节（凋亡）化合物。
• Synthesis of entadamide A and entadamide B isolated from Entada phaseoloides and their inhibitory effects on 5-lipoxygenase.
  作者：Fumio IKEGAMI、Toshikazu SEKINE、Masaki ABURADA、Yuichi FUJII、Yasuhiro KOMATSU、Isamu MURAKOSHI

  DOI：10.1248/cpb.37.1932

  日期：——

  Two new sulfur-containing amides, entadamide A (1) and entadamide B (2), isolated from the seeds of Entada phaseoloides, were synthesized by the addition reaction of methanethiol to propiolic acid (5) followed by condensation with ethanolamine by the use of dicyclohexylcarbadiimide. These compounds inhibited the 5-lipoxygenase activity of RBL-1 cells at 10(-4) g/ml. This finding suggests that entadamides

  从Entada phaseoloides的种子中分离出的两种新的含硫酰胺entadamide A（1）和entadamide B（2）是通过甲硫醇与丙酸（5）的加成反应，然后与乙醇胺缩合合成的二环己基碳二亚胺。这些化合物以10（-4）g / ml抑制RBL-1细胞的5-脂氧合酶活性。这一发现表明，他达米德A和B可能是新型抗炎药的例子。
• Lepadins I–K, 3-<i>O</i>-(3′-Methylthio)acryloyloxy-decahydroquinoline Esters from a Bahamian Ascidian <i>Didemnum</i> sp. Assignment of Absolute Stereostructures
  作者：Sesselja Ómarsdóttir、Xiao Wang、Hong-bing Liu、Brendan M. Duggan、Tadeusz F. Molinski

  DOI：10.1021/acs.joc.8b01609

  日期：2018.11.16

  heterocyclic core in lepadin I, and a new variation, an octahydroquinoline in lepadin J, but differ from earlier reported compounds by acylation of the 3-hydroxyl group by a rare 3′-methylthioacrylate. The absolute configuration of lepadin I was solved by interpretation of NOE measurements, and exciton coupled circular dichroism (ECCD) of the corresponding N-p-bromobenzoyl derivative. The latter constitutes

  从Didemnum sp。的标本中分离出三种十氢异喹啉碱生物碱，Lepadins I-K 。收集在巴哈马。通过对MS，IR和1 H，13 C和2D NMR光谱进行综合分析，确定了新化合物的结构。像先前报道的lepadins一样，新化合物的结构在lepadin I中包含十氢喹啉杂环核心，并在lepadin J中包含新变体octahydroquinoline，但与之前报道的化合物不同之处在于，稀有的3'酰化了3-羟基-甲基硫代丙烯酸酯。lepadin I的绝对构型通过NOE值的解释以及相应N - p的激子耦合圆二色性（ECCD）的解析得到了解决。-溴苯甲酰基衍生物。后者构成确定整个lepadin家族绝对构型的通用方法。远程侧链仲甲醇的构型通过改进的Mosher酯法得以解决。Lepadin I抑制丁酰胆碱酯酶（BuChE，IC 50 3.1μM ），但仅弱抑制乙酰胆碱酯酶（AChE）（100μM时为10％）。
• Entadamide C, a sulphur-containing amide from Entada phaseoloides
  作者：Fumio Ikegami、Toshikazu Sekine、Supanee Duangteraprecha、Noriko Matsushita、Noriko Matsuda、Nijsiri Ruangrungsi、Isamu Murakoshi

  DOI：10.1016/0031-9422(89)80135-9

  日期：1989.1

  been isolated from the leaves of Entada phaseoloides together with entadamide A. The stereostructure including the absolute configuration of entadamide C was established as (R)-(+)-trans-N-(2-hydroxyethyl)-3-methylsulphinylpropenamide, the sulphoxide form of entadamide A, by spectroscopic methods and physical properties. Chemical synthesis of (±)-entadamide C was achieved in three steps from propiolic

  摘要 从 Entada 叶中分离出了第三种新型含硫酰胺 entadamide C 和 entadamide A。立体结构包括 entadamide C 的绝对构型为 (R)-(+)-trans-N- (2-羟乙基)-3-甲基亚磺酰基丙烯酰胺，恩他他胺 A 的亚砜形式，通过光谱方法和物理性质。(±)-entadamide C 的化学合成是从丙炔酸通过三个步骤实现的。

表征谱图