(3-phenylthio)-dioxolane ethyl orthopropionate | 444168-92-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3-phenylthio)-dioxolane ethyl orthopropionate
• 英文别名: 2-ethoxy-2-(2-phenylsulfanylethyl)-1,3-dioxolane
• CAS: 444168-92-7
• 化学式: C₁₃H₁₈O₃S
• 分子量: 254.35
• InChiKey: HKPWXRJSYCMDRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2-丙二烯三正丁基锡 、 (3-phenylthio)-dioxolane ethyl orthopropionate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以70%的产率得到2-(2-(phenylthio)ethyl)-2-(prop-2-yn-1-yl)-1,3-dioxolane
  参考文献：
  名称：

  Total Synthesis of (+)-Azaspiracid-1. An Exhibition of the Intricacies of Complex Molecule Synthesis

  摘要：

  The synthesis of the marine neurotoxin azaspiracid-1 has been accomplished. The individual fragments were synthesized by catalytic enantioselective processes: A hetero-Diels-Alder reaction to afford the E- and HI-ring fragments, a carbonyl-ene reaction to furnish the CD-ring fragment, and a Mukaiyama aldol reaction to deliver the FG-ring fragment. The subsequent fragment couplings were accomplished by aldol and sulfone anion methodologies. All ketalization events to form the nonacyclic target were accomplished under equilibrating conditions utilizing the imbedded configurations of the molecule to adopt one favored conformation. A final fragment coupling of the anomeric EFGHI-sulfone anion to the ABCD-aldehyde completed the convergent synthesis of (+)-azaspiracid-1.

  DOI：

  10.1021/ja804659n
• 作为产物：
  描述：

  3-(苯硫基)丙腈 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3-phenylthio)-dioxolane ethyl orthopropionate
  参考文献：
  名称：

  Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function

  摘要：

  1,1-Dimethyl-3-(phenyldio)-propane 4 was deprotonated with t-BuLi, then converted to the corresponding organocuprate reagent which, in the presence of HMPA and TMSCl was added to a variety of enones to give the corresponding silylenol ethers 7. These were cyclised without purification upon acidic conditions to give the cyclopentannulation products 9. A similar result was obtained with the corresponding orthoester reagent 6. This cyclopentannulation sequence is applicable to a wide variety of enones except for those bearing substituents near the reacting centre. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01248-0