thiovaleric acid | 53966-59-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代酸
• 英文名称: thiovaleric acid
• 英文别名: propylthioacetic acid；pentanethioic S-acid
• CAS: 53966-59-9
• 化学式: C₅H₁₀OS
• 分子量: 118.2
• InChiKey: OTIJNTWWDCIUNM-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  138-140 °C
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thiovaleric acid 在 全氟碘代丁烷 、 二甲基亚砜 作用下， 反应 24.0h， 以92%的产率得到正戊酸
  参考文献：
  名称：

  通过可见光促进的原子取代过程将硫代酸转化为羧酸

  摘要：

  已经开发了一种可见光促进的原子取代反应，用于以二甲亚砜 (DMSO) 作为氧源将硫代酸转化为羧酸，以超过 90% 的产率提供各种烷基和芳基羧酸。通过硫代酸和 DMSO 之间形成的氢键加合物的光化学反应，原子取代过程顺利进行。提出了涉及 DMSO 的质子耦合电子转移 (PCET) 以及同时产生硫基和羟基自由基是实现转化的关键步骤。

  DOI：

  10.1021/acs.orglett.2c00481
• 作为产物：
  描述：

  正戊酸 在 tetraphosphorus decasulfide 作用下， 以 甲苯 为溶剂， 生成 thiovaleric acid
  参考文献：
  名称：

  Adriamycin analogs. Preparation and biological evaluation of some thio ester analogues of adriamycin and N-(trifluoroacetyl)adriamycin 14-valerate

  摘要：

  On the consideration that the highly active DNA-nonbinding adriamycin analogues N-(trifluoroacetyl)adriamycin 14-valerate and N-(trifluoroacetyl)adriamycin 14-O-hemiadipate undergo initial metabolic conversion to N-(trifluoroacetyl)adriamycin by the action of nonspecific serum and tissue esterases, a number of N-(trifluoroacetyl)adriamycin 14-thio esters have been prepared and studied for in vitro growth inhibition, vs. human-derived CCRF-CEM leukemic lymphocytes, and in vivo antitumor activity, vs. murine P388 leukemia, relative to the rate of thio ester deacylation induced by esterases present in mouse serum. Products were obtained by reaction of N-(trifluoroacetyl)-14-bromodaunorubicin with thioacetic, thiopropionic, thiobutyric, thiovaleric, and thiobenzoic acids in ethanol, in the presence of potassium carbonate. Because little is known about similar thio ester derivatives of adriamycin itself, the corresponding adriamycin 14-thio esters were also prepared and evaluated for antitumor activity; with these products, determination of their extent of interaction with calf thymus DNA was also performed. For the adriamycin thio ester products, significant in vivo anti-P388 activity was seen with the thioacetate, thiovalerate, and thiobenzoate derivatives, although no compound matched the curative effects of N-(trifluoroacetyl)adriamycin 14-valerate in this system. With respect to the N-(trifluoroacetyl)adriamycin 14-thio ester products, although the corresponding oxo ester analogues are all significantly biologically active, none of the thio ester derivatives showed activity in vitro or in vivo.

  DOI：

  10.1021/jm00157a025

文献信息

• A Facile Synthesis of Thioacids by Hydrolysis of 1-(Acylthio)ethaniminium Chlorides
  作者：Masaharu Toriyama、Haruo Kamijo、Shigeyasu Motohashi、Toshio Takido、Kunio Itabashi

  DOI：10.1080/10426500307837

  日期：2003.8.1

  A facile method for the preparation of thioacids in moderate to good yields has been developed by hydrolysis of 1-(acylthio)ethaniminium chlorides under a liquid-liquid two phase system consisting of benzene and a sodium hydroxide aqueous solution at room temperature. We have achieved facile preparation of these compounds without use of toxic compounds such as hydrogen sulfide.

  通过在由苯和氢氧化钠水溶液组成的液-液两相系统下，在室温下水解 1-（酰硫基）乙胺氯化物，开发了一种以中等至良好收率制备硫代酸的简便方法。我们已经在不使用硫化氢等有毒化合物的情况下轻松制备了这些化合物。
• Hypoglycemic agent
  申请人：Ajinomoto Co., Inc.

  公开号：US20030191323A1

  公开（公告）日：2003-10-09

  The present invention provides a hypoglycemic agent containing an acylsulfonamide derivative such as a compound of the following formula or an analog thereof, which agent is usable for preventing and curing diabetes: 1

  本发明提供一种降血糖药剂，其中包含一种酰基磺酰胺衍生物，例如下式化合物或其类似物，该药剂可用于预防和治疗糖尿病：1
• 光诱导硝基化合物的一锅法还原酰化方法
  申请人：温州大学

  公开号：CN113956174B

  公开（公告）日：2023-09-22

  本发明公开了光诱导硝基化合物的一锅法还原酰化方法，包括以下步骤：将硝基化合物、硫代羧酸、碳酸氢铵、溶剂加入到反应容器中，在氮气保护下，用LED灯进行照射，室温下反应6～15小时，反应结束后，依次经过后处理和硅胶色谱柱纯化后即得到酰胺化合物。本发明具有以下的有益之处：(1)原料廉价易得；(2)底物范围广；(3)无需额外光敏剂或催化剂；(4)反应条件温和、操作简单；(5)反应收率高。
• TOROSSIAN, D. R.;AUBARD, G. G.;ROUX, C. P. J.
  作者：TOROSSIAN, D. R.、AUBARD, G. G.、ROUX, C. P. J.

  DOI：——

  日期：——
• KOBAYASHI, YOSHIO;TAKIDO, TOSHIO;ITABASHI, KUNIO, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM., 1986, N 4, 619-621
  作者：KOBAYASHI, YOSHIO、TAKIDO, TOSHIO、ITABASHI, KUNIO

  DOI：——

  日期：——