(RS)-7-methoxy-1,4-oxathiepane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (RS)-7-methoxy-1,4-oxathiepane
• 英文别名: 7-Methoxy-1,4-oxathiepane
• 化学式: C₆H₁₂O₂S
• 分子量: 148.226
• InChiKey: UGFFSZKPGOQDBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  5-氟脲嘧啶 、 (RS)-7-methoxy-1,4-oxathiepane 在 三甲基氯硅烷 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以17%的产率得到(RS)-1-(1,4-oxathiepan-7-yl)-5-fluorouracil
  参考文献：
  名称：

  Synthesis of novel 5-fluorouracil derivatives with 1,4-oxaheteroepane moieties

  摘要：

  A series of new ring-expanded isosteres (1,4-oxaheteroepanes) of Ftorafur [1-(2-tetrahydrofuranyl)-5-fluorouracil] has been synthesized. The branching of C-3 of the seven-membered cycloacetal and the electronegativity of the Y group on the 3-YCH2 moities (Y being H, I and Cl), respectively, seem to direct their regiochemical and stereochemical outcome. The more electronegative the group Y is (and favouring accordingly the formation of an external ion pair), the more diastereoselectivity that is reached. The in vitro cytotoxicity versus HT-29 has been tested, showing that cis-3g was the only moderately active compound. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00815-1
• 作为产物：
  描述：

  3-<2-(hydroxyethylthio)propanal> dimethyl acetal 在 三苯基膦 作用下， 以 四氯化碳 为溶剂， 以52%的产率得到(RS)-7-methoxy-1,4-oxathiepane
  参考文献：
  名称：

  Synthesis of novel 5-fluorouracil derivatives with 1,4-oxaheteroepane moieties

  摘要：

  A series of new ring-expanded isosteres (1,4-oxaheteroepanes) of Ftorafur [1-(2-tetrahydrofuranyl)-5-fluorouracil] has been synthesized. The branching of C-3 of the seven-membered cycloacetal and the electronegativity of the Y group on the 3-YCH2 moities (Y being H, I and Cl), respectively, seem to direct their regiochemical and stereochemical outcome. The more electronegative the group Y is (and favouring accordingly the formation of an external ion pair), the more diastereoselectivity that is reached. The in vitro cytotoxicity versus HT-29 has been tested, showing that cis-3g was the only moderately active compound. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00815-1

文献信息

• Espinosa; Gallo; Campos, Il Farmaco, 1991, vol. 46, # SUPPL. 1, p. 253 - 265
  作者：Espinosa、Gallo、Campos、Entrena、Dominguez、Camacho、Pineda de las Infantas

  DOI：——

  日期：——
• ESPINOSA, A.;GALLO, M. A.;CAMPOS, J.;ENTRENA, A.;DOMINGUEZ, J. F.;CAMACHO+, FARMACO, 46,(1991) N, C. 573
  作者：ESPINOSA, A.、GALLO, M. A.、CAMPOS, J.、ENTRENA, A.、DOMINGUEZ, J. F.、CAMACHO+

  DOI：——

  日期：——
• Synthesis of novel 5-fluorouracil derivatives with 1,4-oxaheteroepane moieties
  作者：Jose A. Gómez、María A. Trujillo、Joaquín Campos、Miguel A. Gallo、Antonio Espinosa

  DOI：10.1016/s0040-4020(98)00815-1

  日期：1998.10

  A series of new ring-expanded isosteres (1,4-oxaheteroepanes) of Ftorafur [1-(2-tetrahydrofuranyl)-5-fluorouracil] has been synthesized. The branching of C-3 of the seven-membered cycloacetal and the electronegativity of the Y group on the 3-YCH2 moities (Y being H, I and Cl), respectively, seem to direct their regiochemical and stereochemical outcome. The more electronegative the group Y is (and favouring accordingly the formation of an external ion pair), the more diastereoselectivity that is reached. The in vitro cytotoxicity versus HT-29 has been tested, showing that cis-3g was the only moderately active compound. (C) 1998 Elsevier Science Ltd. All rights reserved.