methyl 1-(3-phenylsulfanylpropyl)-2-oxocyclopentanecarboxylate | 1010832-60-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 1-(3-phenylsulfanylpropyl)-2-oxocyclopentanecarboxylate
• 英文别名: Methyl 2-oxo-1-(3-phenylsulfanylpropyl)cyclopentane-1-carboxylate；methyl 2-oxo-1-(3-phenylsulfanylpropyl)cyclopentane-1-carboxylate
• CAS: 1010832-60-6
• 化学式: C₁₆H₂₀O₃S
• 分子量: 292.399
• InChiKey: LLIWWECWIBIRKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(3-phenylsulfanylpropyl)-2-oxocyclopentanecarboxylate 在 sodium cyanide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以87%的产率得到2-(3-phenylsulfanylpropyl)cyclopentanone
  参考文献：
  名称：

  Synthesis of alkylated indolizidine alkaloids via Pummerer mediated cyclization: synthesis of (±)-indolizidine 167B, (±)-5-butylindolizidine and (±)-monomorine I

  摘要：

  The syntheses of indolizidine alkaloids, i.e., (+/-)-coniceine, (+/-)-indolizidine 167B, (+/-)-5-butylindolizidine and (+/-)-monomorine I via Pummerer cyclization are described. The key step is the transformation of lactam sulfoxide to bicyclic lactam via the Pummerer cyclization. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.013
• 作为产物：
  描述：

  methyl 1-bromopropyl-2-oxocyclopentanoate 、 苯硫酚 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以19.87 g的产率得到methyl 1-(3-phenylsulfanylpropyl)-2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Synthesis of alkylated indolizidine alkaloids via Pummerer mediated cyclization: synthesis of (±)-indolizidine 167B, (±)-5-butylindolizidine and (±)-monomorine I

  摘要：

  The syntheses of indolizidine alkaloids, i.e., (+/-)-coniceine, (+/-)-indolizidine 167B, (+/-)-5-butylindolizidine and (+/-)-monomorine I via Pummerer cyclization are described. The key step is the transformation of lactam sulfoxide to bicyclic lactam via the Pummerer cyclization. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.013

文献信息

• A general strategy to spiro[4.n]alk-2-ene-1,6-diones and spiro[5.n]alk-2-ene-1,7-diones via intramolecular acylation of α-sulfinyl carbanions
  作者：Manat Pohmakotr、Tanasri Bunlaksananusorn、Patoomratana Tuchinda

  DOI：10.1016/s0040-4039(99)01897-3

  日期：2000.1

  A convenient and general synthetic method for spiro[4.n]alk-2-ene-1,6-diones and spiro[5.n]alk-2-ene- 1,7-diones, which involves the intramolecular acylation of an oc-sulfinyl carbanion, is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of alkylated indolizidine alkaloids via Pummerer mediated cyclization: synthesis of (±)-indolizidine 167B, (±)-5-butylindolizidine and (±)-monomorine I
  作者：Chutima Kuhakarn、Phachanee Seehasombat、Thaworn Jaipetch、Manat Pohmakotr、Vichai Reutrakul

  DOI：10.1016/j.tet.2007.12.013

  日期：2008.2

  The syntheses of indolizidine alkaloids, i.e., (+/-)-coniceine, (+/-)-indolizidine 167B, (+/-)-5-butylindolizidine and (+/-)-monomorine I via Pummerer cyclization are described. The key step is the transformation of lactam sulfoxide to bicyclic lactam via the Pummerer cyclization. (C) 2007 Elsevier Ltd. All rights reserved.