tert-butyl 2-fluoro-3-oxo-3-phenyl-2-(phenylthio)propanoate | 1208234-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 2-fluoro-3-oxo-3-phenyl-2-(phenylthio)propanoate
• 英文别名: tert-butyl (2S)-2-fluoro-3-oxo-3-phenyl-2-phenylsulfanylpropanoate
• CAS: 1208234-92-7
• 化学式: C₁₉H₁₉FO₃S
• 分子量: 346.422
• InChiKey: KLPBPYOGMOEJNS-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 2-fluoro-3-oxo-3-phenyl-propionate 、 苯次磺酰氯 在 nickel(II) perchlorate hexahydrate 、 (4R,4'R)-2,2'-(4,6-二苯并呋喃二基)双[4,5-二氢-4-苯基恶唑] 作用下， 以 四氢呋喃 为溶剂， 反应 17.5h， 以80%的产率得到tert-butyl 2-fluoro-3-oxo-3-phenyl-2-(phenylthio)propanoate
  参考文献：
  名称：

  Asymmetric synthesis of α-fluoro-α-sulfenyl-β-ketoesters using DBFOX–Ph/Ni(II) complex

  摘要：

  Enantioselective alpha-sulfenylation of alpha-fluoro-beta-ketoesters 4 with phenylsulfenyl chloride catalyzed by DBFOX-Ph/Ni(II) complex afforded the corresponding alpha-fluoro-alpha-sulfenyl-beta-ketoesters 2 in moderate to good yields with excellent enantiomeric excesses up to 93% ee. alpha-Fluoro-alpha-sulfenyl-beta-ketoesters can be effectively converted to tri-fluorinated alpha-sulfenylcarboxylates by the use of DAST, which should be useful intermediates for the synthesis of non-racemized fluorinated isosteres of pharmaceutically attractive SM32. The enantioselective alpha-phenylsulfenylation as well as alpha-pentafluoro-phenylsulfenylation of non-fluorinated beta-ketoesters 5 were also carried out under the same catalyst conditions affording up to 95% ee of the products 6-8. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.08.004

文献信息

• Asymmetric organocatalytic sulfenylation for the construction of a diheteroatom-bearing tetrasubstituted carbon centre
  作者：Qingfa Tan、Qianping Chen、Zitong Zhu、Xiaohua Liu

  DOI：10.1039/d2cc03443c

  日期：——

  construct diheteroatom-bearing carbon centres was achieved by employing chiral guanidine organocatalysts. This protocol provided a facile route towards the synthesis of α-fluoro-α-sulfenyl-β-ketoamides, azlactone adducts and α-sulfur-substituted amino acid derivatives in high yields with good to excellent enantioselectivities. A possible working mode was proposed to elucidate the chiral control of

  通过使用手性胍有机催化剂，实现了催化对映选择性亚磺酰化构建含二杂原子的碳中心。该协议为以高产率合成 α-氟-α-硫基-β-酮酰胺、azlactone 加合物和 α-硫取代的氨基酸衍生物提供了一条简便的途径，具有良好的对映选择性。提出了一种可能的工作模式来阐明该过​​程的手性控制。
• Asymmetric synthesis of α-fluoro-α-sulfenyl-β-ketoesters using DBFOX–Ph/Ni(II) complex
  作者：Takehisa Ishimaru、Shinichi Ogawa、Etsuko Tokunaga、Shuichi Nakamura、Norio Shibata

  DOI：10.1016/j.jfluchem.2009.08.004

  日期：2009.11

  Enantioselective alpha-sulfenylation of alpha-fluoro-beta-ketoesters 4 with phenylsulfenyl chloride catalyzed by DBFOX-Ph/Ni(II) complex afforded the corresponding alpha-fluoro-alpha-sulfenyl-beta-ketoesters 2 in moderate to good yields with excellent enantiomeric excesses up to 93% ee. alpha-Fluoro-alpha-sulfenyl-beta-ketoesters can be effectively converted to tri-fluorinated alpha-sulfenylcarboxylates by the use of DAST, which should be useful intermediates for the synthesis of non-racemized fluorinated isosteres of pharmaceutically attractive SM32. The enantioselective alpha-phenylsulfenylation as well as alpha-pentafluoro-phenylsulfenylation of non-fluorinated beta-ketoesters 5 were also carried out under the same catalyst conditions affording up to 95% ee of the products 6-8. (C) 2009 Elsevier B.V. All rights reserved.