4-[(12-bromododecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane | 111040-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(12-bromododecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
• 英文别名: 3-O-(12-bromododecyl)-1,2-isopropylideneglycerol；4-(12-Bromododecoxymethyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 111040-69-8
• 化学式: C₁₈H₃₅BrO₃
• 分子量: 379.378
• InChiKey: FYBOUJQHVBIYDF-UHFFFAOYSA-N

物化性质

• 沸点：
  418.9±25.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(12-bromododecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以93%的产率得到4-[(12-azidododecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of Oligonucleotides Carrying Amino Lipid Groups at the 3′-End for RNA Interference Studies

  摘要：

  Novel lipid derivatives carrying amino and triazolyl groups were efficiently synthesized and covalently anchored at the 3'-termini of oligonucleondes The desired amino-lipid conjugates were fully characterized by reversed-phase HPLC and MALDI-TOF mass spectrometry The methodology was applied in the synthesis of lipid-siRNA designed to inhibit necrosis factor (TNF-alpha) in order to obtain siRNAs with anti-inflammatory properties The siRNA duplex carrying amino-lipids at the 3'-end of the passenger strand has inhibitory properties similar to those of unmodified RNA duplexes in HeLa cells. indicating that the new lipid derivatives ate compatible with the RNA interference machinery

  DOI：

  10.1021/jo101143j
• 作为产物：
  描述：

  1,12-二溴十二烷 、 丙酮缩甘油 在 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以47%的产率得到4-[(12-bromododecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of Oligonucleotides Carrying Amino Lipid Groups at the 3′-End for RNA Interference Studies

  摘要：

  Novel lipid derivatives carrying amino and triazolyl groups were efficiently synthesized and covalently anchored at the 3'-termini of oligonucleondes The desired amino-lipid conjugates were fully characterized by reversed-phase HPLC and MALDI-TOF mass spectrometry The methodology was applied in the synthesis of lipid-siRNA designed to inhibit necrosis factor (TNF-alpha) in order to obtain siRNAs with anti-inflammatory properties The siRNA duplex carrying amino-lipids at the 3'-end of the passenger strand has inhibitory properties similar to those of unmodified RNA duplexes in HeLa cells. indicating that the new lipid derivatives ate compatible with the RNA interference machinery

  DOI：

  10.1021/jo101143j

文献信息

• Phospholipid derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04778912A1

  公开（公告）日：1988-10-18

  Phospholipid derivatives of the formula: ##STR1## wherein R.sup.1 is a higher alkyl, acylmethyl or alkylcarbamoyl group which may be substituted by cycloalkyl; R.sup.2 is a lower alkyl which may be substituted by carboxy, formyl or lower acyl, a carbamoyl or thiocarbamoyl group which is substituted by lower alkyl, or an acetoacetyl group; R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen or lower alkyl, or ##STR2## represents a cyclic ammonio group; and n represents an integer of 8 to 14, and salts thereof have antitumor activity.

  磷脂衍生物的化学式为：##STR1## 其中 R.sup.1 是较高的烷基、酰甲基或烷基氨基甲酰基团，可以被环烷基取代；R.sup.2 是较低的烷基，可以被羧基、甲酰基或较低酰基、一个被较低烷基取代的氨基甲酰基或硫代氨基甲酰基团，或一个乙酰乙酰基取代；R.sup.3、R.sup.4 和 R.sup.5 独立地是氢或较低烷基，或 ##STR2## 代表一个环状铵基；n 代表一个整数，范围为 8 到 14，以及其盐具有抗肿瘤活性。
• Phospholipid derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0225129A1

  公开（公告）日：1987-06-10

  Phospholipid derivatives of the formula: wherein R¹ is a higher alkyl, acylmethyl or alkylcarbamoyl group which may be substituted by cycloalkyl; R² is a lower alkyl which may be substituted by carboxy, formyl or lower acyl, a carbamcyl or thiocarbamoyl group which is substituted by lower alkyl, or an acetoacetyl group; R³, R⁴ and R⁵ are independently hydrogen or lower alkyl, or represents a cyclic ammonio group; and n represents an integer of 8 to 14, and salts thereof have antitumor activity and platelet activating factor inhibitory activity and are useful as antitumor agents.

  式中的磷脂衍生物： 其中 R¹ 是可被环烷基取代的高烷基、酰甲基或烷基氨基甲酰基；R² 是可被羧基、甲酰基或低级酰基、被低级烷基取代的氨基甲酰基或硫代氨基甲酰基或乙酰乙酰基取代的低级烷基；R³、R⁴ 和 R⁵ 独立地为氢或低级烷基，或代表环氨基团；n 代表 8 至 14 的整数。 代表环状铵基；以及 n 代表 8 至 14 的整数，其盐类具有抗肿瘤活性和血小板活化因子抑制活性，可用作抗肿瘤剂。
• US4778912A
  申请人：——

  公开号：US4778912A

  公开（公告）日：1988-10-18
• [EN] LIPOPHILIC DERIVATIVES OF NUCLEIC ACIDS<br/>[ES] DERIVADOS LIPOFÍLICOS DE ÁCIDOS NUCLEICOS<br/>[FR] DÉRIVÉS LIPOPHILES D'ACIDES NUCLÉIQUES
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2011135138A1

  公开（公告）日：2011-11-03

  En esta invención se describen nuevos derivados del pARNi. El pARNi modificado según la invención mejora su entrada en las células y su estabilidad a la degradación por nucleasas, aumentando la capacidad inhibitoria de los pARNi. Estos nuevos compuestos contienen lípidos unidos a una molécula puente presente en el extremo terminal del dúplex de pARNi mediante enlaces tipo éter. También se describe la síntesis de dichos compuestos.
• Synthesis of Oligonucleotides Carrying Amino Lipid Groups at the 3′-End for RNA Interference Studies
  作者：Santiago Grijalvo、Sandra M. Ocampo、José C. Perales、Ramon Eritja

  DOI：10.1021/jo101143j

  日期：2010.10.15

  Novel lipid derivatives carrying amino and triazolyl groups were efficiently synthesized and covalently anchored at the 3'-termini of oligonucleondes The desired amino-lipid conjugates were fully characterized by reversed-phase HPLC and MALDI-TOF mass spectrometry The methodology was applied in the synthesis of lipid-siRNA designed to inhibit necrosis factor (TNF-alpha) in order to obtain siRNAs with anti-inflammatory properties The siRNA duplex carrying amino-lipids at the 3'-end of the passenger strand has inhibitory properties similar to those of unmodified RNA duplexes in HeLa cells. indicating that the new lipid derivatives ate compatible with the RNA interference machinery