(RS)-(3-氯-2-羟基丙氧基)丙醛二甲基缩醛 | 191666-40-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 中文名称: (RS)-(3-氯-2-羟基丙氧基)丙醛二甲基缩醛
• 英文名称: (RS)-(3-chloro-2-hydroxypropoxy)propanal dimethyl acetal
• 英文别名: 1-Chloro-3-(3,3-dimethoxypropoxy)propan-2-ol
• CAS: 191666-40-7
• 化学式: C₈H₁₇ClO₄
• 分子量: 212.674
• InChiKey: MQJNNEYZQSJCBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (RS)-(3-氯-2-羟基丙氧基)丙醛二甲基缩醛 在 lithium aluminium tetrahydride 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到3-(2-hydroxypropoxy)propanal dimethyl acetal
  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：

  甲醇 、 2-<2-(3-chloro-2-hydroxypropoxy)ethyl>-4-chloromethyl-1,3-dioxolane 在 硫酸 作用下， 反应 6.0h， 以57%的产率得到(RS)-(3-氯-2-羟基丙氧基)丙醛二甲基缩醛
  参考文献：
  名称：

  Chemical modifications on the acyclic moiety of 3-(2-hydroxyethoxy)-1-alkoxypropyl nucleobases. 2. Differentiation and growth inhibition in rhabdomyosarcoma cells after exposure to a novel 5-fluorouracil acyclonucleoside

  摘要：

  A series of new 5FU acyclonucleoside analogues has been synthesized and tested for their in vitro cytotoxicity versus HT-29 colon carcinoma. The only active compound is 1-{[3-(3-cloro-2-hydroxypropoxy)-1-methoxy]propoxy}-5-fluorouracil 14, which is 8-fold less active than 5-fluorouracil. The rest of the newly prepared compounds showed no significant activity We selected 14 as the drug in the treatment of an human embryonal cell line RD derived from rhabdomyosarcoma. Such treatment caused time-dependent growth inhibition. Interestingly, RD cells treated with 14 at a concentration of 90 mu M for 6 days showed phenotypic differentiation, with increased expression of desmin, alpha-actinin and tropomyosin. We conclude that exposure of this human embryonal rhabdomyosarcoma cell line to a 90 mu M concentration released the neoplastic cells from their blockade, allowing them to recover normal myogenic development. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00415-8