Acetylthioessigsaeure-S-benzylester | 54565-04-7

• 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: Acetylthioessigsaeure-S-benzylester
• 英文别名: S-benzyl 3-oxobutanethioate
• CAS: 54565-04-7
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: NZYHIRUBIHPRBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetylthioessigsaeure-S-benzylester 在 乙酸铵 、 氢氧化钾 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 18.25h， 生成 1-Ethyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbothioic acid di-S-benzyl ester
  参考文献：
  名称：

  Esters of 1,4-dihydropyridine-3- and -3,5-carbothiolic acids

  摘要：

  DOI：

  10.1007/bf00512963
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 、 苄硫醇 以 甲苯 为溶剂， 以95%的产率得到Acetylthioessigsaeure-S-benzylester
  参考文献：
  名称：

  Synthesis of 1,3-dioxin-4-ones and their use in synthesis. Part XXIV. A novel synthesis of .BETA.-ketothioesters.

  摘要：

  本文描述了一种新的通用一步法，通过在适当的无质子溶剂中加热6-单取代和5,6-双取代的1,3-二氧杂环-4-酮与硫醇，实现高产率合成S-烷基β-酮硫酯。该方法适用于大规模制备多种β-酮硫酯。

  DOI：

  10.1248/cpb.38.2262

文献信息

• Synthesis of 1,3-dioxin-4-ones and their use in synthesis. Part XXIV. A novel synthesis of .BETA.-ketothioesters.
  作者：Jun-ichi SAKAKI、Satoshi KOBAYASHI、Masayuki SATO、Chikara KANEKO

  DOI：10.1248/cpb.38.2262

  日期：——

  A new general one-pot method for high-yield synthesis of S-alkyl β-ketothioesters by heating of 6-mono- and 5, 6-disubstituted 1, 3-dioxin-4-ones and thiols in an appropriate aprotic solvent is described. This procedure is available for large-scale preparation of a variety of β-ketothioesters.

  本文描述了一种新的通用一步法，通过在适当的无质子溶剂中加热6-单取代和5,6-双取代的1,3-二氧杂环-4-酮与硫醇，实现高产率合成S-烷基β-酮硫酯。该方法适用于大规模制备多种β-酮硫酯。
• Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
  作者：Naomi Sakai、Nathalie Sordé、Stefan Matile

  DOI：10.3390/61100845

  日期：——

  We report that a subtle balance of carbanion reactivity, leaving group activation, and pKa of the catalyst is required for efficient self-condensation of thiomalonates to thioacetoacetates in up to 71% yield under “biomimetic” conditions originally proposed by Kobuke and Yoshida (Tetrahedron Lett. 1978, 19, 367).

  我们报告说，在 Kobuke 和 Yoshida 最初提出的 "仿生 "条件下（Tetrahedron Lett.）
• Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay
  作者：Datta E. Ponde、Vishnu H. Deshpande、Vivek J. Bulbule、Arumugam Sudalai、Anil S.Gajare

  DOI：10.1021/jo971404l

  日期：1998.2.1

  Transesterification and transthiolesterification of beta-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding beta-keto esters in high yields. For the first time, transthiolesterification of beta-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of beta-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding beta-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward beta-keto esters is also described. Sterically hindered carbonyl groups as well as alpha,beta-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.
• SAKAKI, JUN-ICHI;KOBAYASHI, SATOSHI;SATO, MASAYUKI;KANEKO, CHIKARA, CHEM. AND PHARM. BULL., 38,(1990) N, C. 2262-2264
  作者：SAKAKI, JUN-ICHI、KOBAYASHI, SATOSHI、SATO, MASAYUKI、KANEKO, CHIKARA

  DOI：——

  日期：——
• VIGANTE, B. A.;OZOLS, YA. YA.;DUBUR, G. YA.;BEJLIS, YU. I.;BELASH, E. M.;+, XIMIYA GETEROTSIKL. SOEDIN., 1982, N 2, 219-228
  作者：VIGANTE, B. A.、OZOLS, YA. YA.、DUBUR, G. YA.、BEJLIS, YU. I.、BELASH, E. M.、+

  DOI：——

  日期：——