(+/-)-5-methyl-3-phenylsulfanylfuran-2(5H)-one | 54144-99-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+/-)-5-methyl-3-phenylsulfanylfuran-2(5H)-one
• 英文别名: 5-methyl-3-phenylsulfanyl-2(5H)-furanone；3-Phenylthio-5-methyl-2(5H)-furanone；5-methyl-3-phenylsulfanyl-5H-furan-2-one；5-Methyl-3-phenylthio-2(5H)-furanon；5-Methyl-3-(phenylthio)-2(5H)-furanone；2-methyl-4-phenylsulfanyl-2H-furan-5-one
• CAS: 54144-99-9
• 化学式: C₁₁H₁₀O₂S
• 分子量: 206.265
• InChiKey: SNDQWXNSRKBKPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (+/-)-5-methyl-3-phenylsulfanylfuran-2(5H)-one 生成 4-(benzenesulfinyl)-2-methyl-2H-furan-5-one
  参考文献：
  名称：

  WATANABE, MITSUAKI;TSUKAZAKI, MASAO;HAMADA, YUMIKO;IWAO, MASATOMO;FURUKAW+, CHEM. AND PHARM. BULL., 37,(1989) N1, C. 2948-2951

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-dihydro-5-methyl-3-(phenylthio)furan-2(3H)-one 在 sodium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 生成 (+/-)-5-methyl-3-phenylsulfanylfuran-2(5H)-one
  参考文献：
  名称：

  通过电解进行新的合成反应。三，硫化物的α-乙酰氧基化

  摘要：

  通过在乙酸中进行电解，可以将硫化物直接有效地直接转化为相应的α-乙酰氧基硫化物。

  DOI：

  10.1016/0040-4039(80)80128-6

文献信息

• An efficient synthesis of 2(5H)-furanone and furan derivatives using 3-(phenylthio)propenal as a 1,3-dipolar synthon.
  作者：Mitsuaki WATANABE、Masao TSUKAZAKI、Yoshiaki HIRAKAWA、Masatomo IWAO、Sunao FURUKAWA

  DOI：10.1248/cpb.37.2914

  日期：——

  Various 2(5H)-furanone and furan derivatives were synthesized from 3-(phenylthio)propenal by a one-pot process via carbonyl addition of a range of organometallic reagents and subsequent sulfide-directed α-lithiatin followed by electrophilic trapping. This methodology was successfuly applied to the syntheses of quercus lactone and 2, 5-diarylfuran natural products.

  通过一锅法工艺，通过一系列有机金属试剂的羰基加成，随后进行硫醚导向的α-锂化，并最终进行亲电捕获，从3-（苯硫基）丙烯醛合成了各种2（5H）-呋喃酮和呋喃衍生物。该方法成功应用于栎素和2,5-二芳基呋喃天然产物的合成。
• Diastereoselective synthesis of γ-hydroxy α,β-epoxyesters and their conversion into β-hydroxy α-sulfenyl γ-butyrolactones
  作者：Santiago Rodríguez、María Kneeteman、Javier Izquierdo、Irakusne López、Florenci V. González、Gabriel Peris

  DOI：10.1016/j.tet.2006.09.030

  日期：2006.11

  corresponding Grignard reagent and were used as a racemic mixture. The resulting γ-hydroxy α,β-epoxyesters were treated with thiophenol for transformation into α-phenylsulfanyl trisubstituted γ-butyrolactones. The syn,syn-lactones isomerize easily in basic media into the syn,anti structures. In order to explain this interconversion, a retroaldol–aldol sequence has been proposed and a sulfur–oxygen

  研究了γ-羟基-α，β-不饱和酯的亲核环氧化的非对映选择性。通过用相应的格氏试剂处理（E）-4-氧代-2-丁烯酸乙酯获得γ-羟基-α，β-不饱和酯，并将其用作外消旋混合物。用硫酚处理所得的γ-羟基α，β-环氧酯，以转化为α-苯基硫烷基三取代的γ-丁内酯。该SYN，顺式内酯在碱性介质进入很容易异构顺，反结构。为了解释这种相互转化，提出了逆醛醇-羟醛序列，并调用了硫-氧相互作用来解释顺式。 分子内羟醛反应产生的α-硫代羟醛的立体化学偏好。
• Stannylfuranones in synthesis: Highly enantioselective preparation of (+)-hamabiwalactone B
  作者：Alexandre M.E. Richecoeur、J.B. Sweeney

  DOI：10.1016/s0040-4039(98)01946-7

  日期：1998.11

  An unambiguous and highly enantioselective total synthesis of the naturally-occurring 2(5H)-furanone hamabiwalactone B has been achieved. The key step is a Stille coupling of novel stannylfuranone 2 with (E)-iodoalkene 3, The enantiomeric purity of the synthetic natural product was greater than or equal to 99%, as judged by chiral HPLC, (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Richecœur, Alexandre M. E.; Sweeney, Tetrahedron, 2000, vol. 56, # 3, p. 389 - 395
  作者：Richecœur, Alexandre M. E.、Sweeney

  DOI：——

  日期：——
• WATANABE, MITSUAKI;TSUKAZAKI, MASAO;HIRAKAWA, YOSHIAKI;IWAO, MASATOMO;FUR+, CHEM. AND PHARM. BULL., 37,(1989) N1, C. 2914-2919
  作者：WATANABE, MITSUAKI、TSUKAZAKI, MASAO、HIRAKAWA, YOSHIAKI、IWAO, MASATOMO、FUR+

  DOI：——

  日期：——