4,4-(Ethylenedioxy)pentyl phenyl sulfide | 97600-68-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,4-(Ethylenedioxy)pentyl phenyl sulfide
• 英文别名: 5-phenylthiopentan-2-one ethylene acetal；1,3-Dioxolane, 2-methyl-2-[3-(phenylthio)propyl]-；2-methyl-2-(3-phenylsulfanylpropyl)-1,3-dioxolane
• CAS: 97600-68-5
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: SHYZPKUKFADYRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-(Ethylenedioxy)pentyl phenyl sulfide 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到4,4-(Ethylenedioxy)pentyl phenyl sulfone
  参考文献：
  名称：

  Ring Contraction of Cyclobutanes and a Novel Cascade Reaction: Application to Synthesis of (.+-.)-Anthoplalone and (.+-.)-Lepidozene

  摘要：

  Two efficient and practical synthetic methodologies for the construction of small ring systems have been developed. The first method involves a novel rearrangement of cyclobutanes 10 and 14 leading to cyclopropanes 11 and 15 employing BF3.OEt(2) or POCl3 in the presence of pyridine or Raney nickel. The second method utilizes a novel cascade reaction of alpha,beta-unsaturated esters 25 and 36 possessing a cyclopropyl ketone moiety with TMSI in the presence of(TMS)(2)NH to afford polycyclic cyclobutane derivatives 26 and 38. A synthesis of(+/-)-anthoplalone (41) and a formal synthesis of (+/-)-lepidozene (42) were achieved utilizing 15, obtained by the above method.

  DOI：

  10.1021/jo00105a028
• 作为产物：
  描述：

  5-氯-2-戊酮 在 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 4,4-(Ethylenedioxy)pentyl phenyl sulfide
  参考文献：
  名称：

  Cornish Christopher A.; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2585 - 2598

  摘要：

  DOI：

文献信息

• Hoshi, Nobuto; Uda, Hisashi, Journal of Chemical Research, Miniprint, 1985, # 3, p. 925 - 945
  作者：Hoshi, Nobuto、Uda, Hisashi

  DOI：——

  日期：——
• CORNISH, CH. A.;WARREN, S., J. CHEM. SOC. PERKIN TRANS., 1985, N 12, 2585-2598
  作者：CORNISH, CH. A.、WARREN, S.

  DOI：——

  日期：——
• Cornish Christopher A.; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2585 - 2598
  作者：Cornish Christopher A.、Warren, Stuart

  DOI：——

  日期：——
• Ring Contraction of Cyclobutanes and a Novel Cascade Reaction: Application to Synthesis of (.+-.)-Anthoplalone and (.+-.)-Lepidozene
  作者：Masataka Ihara、Takahiko Taniguchi、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo00105a028

  日期：1994.12

  Two efficient and practical synthetic methodologies for the construction of small ring systems have been developed. The first method involves a novel rearrangement of cyclobutanes 10 and 14 leading to cyclopropanes 11 and 15 employing BF3.OEt(2) or POCl3 in the presence of pyridine or Raney nickel. The second method utilizes a novel cascade reaction of alpha,beta-unsaturated esters 25 and 36 possessing a cyclopropyl ketone moiety with TMSI in the presence of(TMS)(2)NH to afford polycyclic cyclobutane derivatives 26 and 38. A synthesis of(+/-)-anthoplalone (41) and a formal synthesis of (+/-)-lepidozene (42) were achieved utilizing 15, obtained by the above method.