(甲硫基)乙酸丁酯 | 67746-25-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (甲硫基)乙酸丁酯
• 英文名称: butyl 2-(methylsulfanyl)acetate
• 英文别名: butyl 2-(methylthio)acetate；butyl (methylthio)acetate；n-butyl (methylthio) acetate；n-butyl (methylthio)-acetate；butyl 2-methylsulfanylacetate
• CAS: 67746-25-2
• 化学式: C₇H₁₄O₂S
• 分子量: 162.253
• InChiKey: QXJSYAFLDDZIQI-UHFFFAOYSA-N

物化性质

• LogP：
  2.083 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (甲硫基)乙酸丁酯 在 IF₅-5CH₂Cl₂ 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以89%的产率得到butyl α,α-difluoro-α-(methylthio)acetate
  参考文献：
  名称：

  IF5对硫化苄的脱硫二氟化反应

  摘要：

  具有酯、酮、腈或酰胺等官能团的苄基硫化物的脱硫二氟化反应通过与IF5反应进行。因此，可以选择性地获得gem-二氟化合物。1 特别是 αα-二氟羰基化合物，广泛用于生物有机和药物化学的各个领域。2 已经开发了几种合成αα-二氟羰基化合物的方法，例如α-硫代羰基化合物的Pummerer型氟化，3羰基化合物的亲电氟化，2b,4α-酮羰基化合物的脱氧氟化，5和构建-块方法。6 α-硫代羰基化合物的普默尔型二氟化反应在温和条件下进行。然而，从产物中除去硫基是困难的。α-酮羰基化合物与（二乙氨基）三氟化硫（DAST）或 Deoxofluor 的脱氧氟化反应经常用于合成αα-二氟羰基化合物。然而，当该方法用于与α-二酮反应合成αα-二氟酮时，很难区分底物中的两个羰基，并且会发生不希望的副反应，如多氟化反应。5c,d 如多氟化反应。5c,d 如多氟化反应。5c,d

  DOI：

  10.1055/s-0028-1087511
• 作为产物：
  描述：

  α-(methylthio)acetic acid anhydride 、 正丁醇 在 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 反应 120.0h， 生成 (甲硫基)乙酸丁酯
  参考文献：
  名称：

  (Methylsulfanyl)alkanoate ester biosynthesis in Actinidia chinensis kiwifruit and changes during cold storage

  摘要：

  Four 3-(methylsulfanyl)propionate esters, ethyl 3-(methylsulfanyl)prop-2-enoate, two 2-(methylsulfanyl)acetate esters and their possible precursors 2-(methylsulfanyl)ethanol, 3-(methylsulfanyl)propanol and 3-(methylsulfanyl)propanal were quantified from the headspace of Actinidia chinensis 'Hort 16A' kiwifruit pulp by GC-MS-TOF analysis. The majority of these compounds were specific for eating-ripe fruit and their levels increased in parallel with the climacteric rise in ethylene, accumulating towards the very soft end of the eating firmness. No ethylene production could be observed after long-term storage (4-6 months) at 1.5 degrees C and the levels of all methylsulfanyl-volatiles, except methional, declined by 98-100% during that period. This depletion of (methylsulfanyl)alkanoate-esters after prolonged cold storage points towards little flavour impact of these compounds on commercial 'Hort 16A' kiwifruits. However, ethyl 3-(methylsulfanyl)propionate is suggested to be odour active in ripe 'Hort 16A' fruit that has not been stored. Gene expression measured by q-RT PCR of six ripening-specific alcohol acyltransferase (AAT) expressed sequence tags and (methylsulfanyl)alkanoate-ester production of cell-free extracts were also significantly decreased after prolonged cold storage. However, (methylsulfanyl)alkanoate-ester synthesis of cell-free extracts and AAT gene transcript levels could be recovered by ethylene treatment after five months at 1.5 degrees C indicating that the biosynthesis of (methylsulfanyl)alkanoate-esters in 'Hort 16A' kiwifruit is likely to depend on ethylene-regulated AAT-gene expression. That the composition but not the concentration of (methylsulfanyl)alkanoate-esters in fresh fruit could be restored after ethylene treatment suggests that substrate availability might also have an impact on the final levels of these volatiles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.01.016

文献信息

• Design of .alpha.-alkyl-.beta.-hydroxy esters suitable for providing optical resolution by lipase hydrolysis
  作者：Toshiyuki Itoh、Keiko Kuroda、Miki Tomosada、Yumiko Takagi

  DOI：10.1021/jo00002a054

  日期：1991.1

  A study of the lipase-catalyzed hydrolyses of various alpha-substituted beta-acetoxy esters revealed that a sulfur functional group in the ester, which could play an important role in the stereorecognition by lipase A6 (Aspergillus sp.) and an anti conformation in the ester, promotes satisfactory results in the hydrolysis.
• ITOH, TOSHIYUKI;KURODA, KEIKO;TOMOSADA, MIKI;TAKAGI, YUMIKO, J. ORG. CHEM., 56,(1991) N, C. 797-804
  作者：ITOH, TOSHIYUKI、KURODA, KEIKO、TOMOSADA, MIKI、TAKAGI, YUMIKO

  DOI：——

  日期：——
• Characterisation of two alcohol acyltransferases from kiwifruit (Actinidia spp.) reveals distinct substrate preferences
  作者：Catrin S. Günther、Christian Chervin、Ken B. Marsh、Richard D. Newcomb、Edwige J.F. Souleyre

  DOI：10.1016/j.phytochem.2011.02.026

  日期：2011.6

  Volatile esters are key compounds of kiwifruit flavour and are formed by alcohol acyltransferases that belong to the BAHD acyltransferase superfamily. Quantitative RT-PCR was used to screen kiwifruit-derived expressed sequence tags with proposed acyltransferase function in order to select ripening-specific sequences and test their involvement in alcohol acylation. The screening criterion was for at least 10-fold increased transcript accumulation in ripe compared with unripe kiwifruit and in response to ethylene. Recombinant expression in yeast revealed alcohol acyltransferase activity for Actinidia-derived AT1, AT16 and the phylogenetically distinct AT9, using various alcohol and acyl-CoA substrates. Functional characterisation of AT16 and AT9 demonstrated striking differences in their substrate preferences and apparent catalytic efficiencies (V-max' K-m(-1)). Thus revealing benzoyl-CoA:alcohol O-acyltransferase activity for AT16 and acetyl-CoA:alcohol O-acyltransferase activity for AT9. Both kiwifruit-derived enzymes displayed higher reaction rates with butanol compared with ethanol, even though ethanol is the main alcohol in ripe fruit. Since ethyl acetate and ethyl benzoate are major esters in ripe kiwifruit, we suggest that fruit characteristic volatile profiles result from a combination of substrate availability and specificity of individual alcohol acyltransferases. (C) 2011 Elsevier Ltd. All rights reserved.
• COMPOSITION FOR FORMING CONDUCTIVE FILM
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150275015A1

  公开（公告）日：2015-10-01

  A composition is provided for forming a conductive film. The composition includes a metal compound, a reducing agent, an ionic compound and/or a polar compound, and a compound having at least one atom selected from a nitrogen atom, a sulfur atom and a phosphorus atom. The composition may be an ink composition for coating on an electronic device.
• US8084644B2
  申请人：——

  公开号：US8084644B2

  公开（公告）日：2011-12-27