3-(Z)-(benzylsulfanyl)propenoic acid | 13831-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(Z)-(benzylsulfanyl)propenoic acid
• 英文别名: (Z)-3-benzenesulfanylpropenoic acid；cis-3-benzylsulfanyl-acrylic acid；cis-3-Benzylmercapto-acrylsaeure；(2Z)-3-benzylsulfanyl-acrylic acid；cis-β-Benzylmercapto-acrylsaeure；cis-3-Benzylthioacrylsaeure；(Z)-3-benzylsulfanylprop-2-enoic acid
• CAS: 13831-02-2
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: PILARZPCBNUNMH-SREVYHEPSA-N

物化性质

• 熔点：
  144-145 °C
• 沸点：
  355.2±35.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  3-(Z)-(benzylsulfanyl)propenoic acid 生成 3-(benzylthio)acrylic acid
  参考文献：
  名称：

  Owen; Sultanbawa, Journal of the Chemical Society, 1949, p. 3112

  摘要：

  DOI：
• 作为产物：
  描述：

  苄硫醇 、 丙炔酸 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 3-(Z)-(benzylsulfanyl)propenoic acid
  参考文献：
  名称：

  合成替代丁烯内酯

  摘要：

  常见的是第二类典型的Darstellung von Butenoliden des Typs II，第二种是Kondensation的二聚体Verbindungen mitβ-Mercapto-acrylesterngemacht wurden。

  DOI：

  10.1002/hlca.19660490632

文献信息

• Substituted isothiazolones
  申请人：Beers A. Scott

  公开号：US20060293374A1

  公开（公告）日：2006-12-28

  This invention is directed to a compound of Formula (I): and pharmaceutically acceptable forms thereof useful as inhibitors of cPLA 2 and a method for preventing, treating or ameliorating a cPLA 2 mediated inflammatory related disease, disorder or condition using a compound of Formula (I) and, more particularly, for preventing, treating or ameliorating a cPLA 2 mediated inflammatory related disease, disorder or condition which results from the cellular secretion of TXB 2 or LTB 4 .

  这项发明涉及一种化合物，其化学式为（I）： 及其药学上可接受的形式，用作cPLA 2 的抑制剂，以及使用化合物（I）预防、治疗或改善由cPLA 2 介导的炎症相关疾病、紊乱或状况的方法，更具体地说，用于预防、治疗或改善由细胞分泌TXB 2 或LTB 4 引起的cPLA 2 介导的炎症相关疾病、紊乱或状况。
• Facile Synthesis of<i>N</i>-Substituted Isothiazol-3(2<i>H</i>)-Ones Using a Hypervalent Iodine(III) Re Agent
  作者：Iou-Jiun Kang、Huey-Min Wang、Hsin-Yu Huang、Ling-Ching Chen

  DOI：10.1002/jccs.200100174

  日期：2001.12

  Treatment of N-substituted (Z)-3-(benzylsulfanyl)propenamides (4) with phenyliodine(III) bis(trifluoroacetate) containing trifluoroacetic acid resulted in an interrupted Pummerer-type reaction to give N-substituted isothiazol-3(2H)-ones (5) rather than the normal Pummerer-type products.

  N-取代的 (Z)-3-(苄基硫烷基)丙烯酰胺 (4) 用含有三氟乙酸的苯碘 (III) 双(三氟乙酸) 处理导致中断的 Pummerer 型反应得到 N-取代的异噻唑-3(2H)- (5) 而不是普通的 Pummerer 型产品。
• Beeley, Nigel R. A.; Harwood, Laurence M.; Hedger, Paul C., Journal of the Chemical Society. Perkin transactions I, 1994, # 16, p. 2245 - 2252
  作者：Beeley, Nigel R. A.、Harwood, Laurence M.、Hedger, Paul C.

  DOI：——

  日期：——
• Synthesis of isothiazol-3-one derivatives as inhibitors of histone acetyltransferases (HATs)
  作者：Stephen Gorsuch、Vassilios Bavetsias、Martin G. Rowlands、G. Wynne Aherne、Paul Workman、Michael Jarman、Edward McDonald

  DOI：10.1016/j.bmc.2008.11.079

  日期：2009.1

  High-throughput screening led to the identification of isothiazolones 1 and 2 as inhibitors of histone acetyltransferase (HAT) with IC50s of 3 mu M and 5 mu M, respectively. Analogues of these hit compounds with variations of the N-phenyl group, and with variety of substituents at C-4, C-5 of the thiazolone ring, were prepared and assayed for inhibition of the HAT enzyme PCAF. Potency is modestly favoured when the N-aryl group is electron deficient (4-pyridyl derivative 10 has IC50 = 1.5 mu M); alkyl substitution at C-4 has little effect, whilst similar substitution at C-5 causes a significant drop in potency. The ring-fused compound 38 has activity (IC50 = 6.1 mu M) to encourage further exploration of this bicyclic structure. The foregoing SAR is consistent with an inhibitory mechanism involving cleavage of the S-N bond of the isothiazolone ring by a catalytically important thiol residue. (C) 2008 Elsevier Ltd. All rights reserved.
• Steric effects in the intramolecular carboxyl-catalyzed hydrolysis of sulfonamides. Ab initio quantum chemical studies of the pentacoordinated sulfur intermediate
  作者：Teun Graafland、Wim C. Nieuwpoort、Jan B. F. N. Engberts

  DOI：10.1021/ja00405a033

  日期：1981.7