4-(9-methoxymethoxynonyl)-2,2-dimethyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(9-methoxymethoxynonyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: 4-[9-(Methoxymethoxy)nonyl]-2,2-dimethyl-1,3-dioxolane
• 化学式: C₁₆H₃₂O₄
• 分子量: 288.428
• InChiKey: BDEJFICAUCEMBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(9-methoxymethoxynonyl)-2,2-dimethyl-1,3-dioxolane 在 2,2'-联吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 15.0h， 以96%的产率得到1,2-O-Isopropyliden-1,2-dihydroxyundecan-11-ol
  参考文献：
  名称：

  Selective Deprotection of Methylene Acetal and MOM Ether in the Presence of Ketal-Type Protective Groups: Remarkable Effect of TBSOTf

  摘要：

  A novel procedure for highly selective deprotection of methylene acetals and MOM (methoxymethyl) groups in the presence of ketal-type protective groups has been developed. The method, which utilizes a combination of TBSOTf and 2,2'-bipyridyl, displays a completely opposite selectivity compared with those of acid-mediated deprotection protocols.

  DOI：

  10.3987/com-12-s(n)43
• 作为产物：
  描述：

  10-十一烯-1-醇 在 disodium hydrogenphosphate 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 tin(ll) chloride 、 lithium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 61.0h， 生成 4-(9-methoxymethoxynonyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Conversion of Epoxides to 1,3-Dioxolanes Catalyzed by Tin(II) Chloride

  摘要：

  Anhydrous tin(II) chloride is an efficient catalyst for the reaction of epoxides with acetone to prepare 2,2-dimethyl-1,3-dioxolanes (acetonides) in good to excellent yields. Mono-, di-, and trisubstituted epoxides participate equally well in this diastereospecific reaction. The use of single enantiomer epoxides under the reported conditions results in significant erosion of optical activity.

  DOI：

  10.1021/jo035112y

文献信息

• Conversion of Epoxides to 1,3-Dioxolanes Catalyzed by Tin(II) Chloride
  作者：James R. Vyvyan、Jennifer A. Meyer、Korin D. Meyer

  DOI：10.1021/jo035112y

  日期：2003.11.1

  Anhydrous tin(II) chloride is an efficient catalyst for the reaction of epoxides with acetone to prepare 2,2-dimethyl-1,3-dioxolanes (acetonides) in good to excellent yields. Mono-, di-, and trisubstituted epoxides participate equally well in this diastereospecific reaction. The use of single enantiomer epoxides under the reported conditions results in significant erosion of optical activity.
• Selective Deprotection of Methylene Acetal and MOM Ether in the Presence of Ketal-Type Protective Groups: Remarkable Effect of TBSOTf
  作者：Hiromichi Fujioka、Tomohiro Maegawa、Yasuyuki Koutani、Kento Senami、Kenzo Yahata

  DOI：10.3987/com-12-s(n)43

  日期：——

  A novel procedure for highly selective deprotection of methylene acetals and MOM (methoxymethyl) groups in the presence of ketal-type protective groups has been developed. The method, which utilizes a combination of TBSOTf and 2,2'-bipyridyl, displays a completely opposite selectivity compared with those of acid-mediated deprotection protocols.