2-(dichloromethyl)-2-hydroxytetrahydrofuran | 137777-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-(dichloromethyl)-2-hydroxytetrahydrofuran
• 英文别名: 2-(dichloromethyl)tetrahydrofuran-2-ol；2-(Dichloromethyl)oxolan-2-ol
• CAS: 137777-18-5
• 化学式: C₅H₈Cl₂O₂
• 分子量: 171.023
• InChiKey: PVJGWSHZCXGENZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(dichloromethyl)-2-hydroxytetrahydrofuran 在 三乙基硅烷 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以65%的产率得到呋喃,2-(二氯甲基)四氢-
  参考文献：
  名称：

  Reactivity of in situ generated dihalomethyllithium towards dicarboxylic acid diesters and lactones: Synthetic applications

  摘要：

  The reaction of dicarboxylic acid diesters 1, with in situ generated dihalomethyllithium (1:1.4 molar ratio) at -78-degrees-C leads, after hydrolysis, to the corresponding dihalomethylketoesters 3. The same process using an excess of the carbenoid (1:4 molar ratio) yields the expected tetrahalodiketones 5. The reaction of these carbenoids with gamma- and delta-lactones 6 at -78-degrees-C yields, after hydrolysis, 2-(dihalomethyl) gamma- or delta-lactols 7 or 8, respectively. The reaction of lactols 7 or 8 with triethylsilane or allyltrimethylsilane in the presence of BF3.OEt2 affords the corresponding substituted tetrahydrofurans or pyrans 10 or 12. The use of epsilon-caprolactone as starting material in the reaction with dihalomethyllithium leads to the corresponding 1,1-dihalo-7-hydroxy-2-heptanones.

  DOI：

  10.1016/s0040-4020(01)81943-8
• 作为产物：
  描述：

  在 TClCA 作用下， 以 水 、 乙腈 为溶剂， 以99%的产率得到2-(dichloromethyl)-2-hydroxytetrahydrofuran
  参考文献：
  名称：

  炔丙醇的区域选择性二卤水合反应：金催化和非催化反应

  摘要：

  通过在金催化剂存在下用 N-碘代琥珀酰亚胺处理，实现了炔丙醇区域选择性转化为先前未报道的 α,α-二碘-β-羟基酮。在无催化剂的情况下用三氯异氰尿酸处理得到相应的α,α-二氯-β-羟基酮。后一个反应可以扩展到其他炔醇。这些转化可用于制备潜在有用的卤化结构单元。初步机理研究表明，该反应涉及乙腈溶剂参与 5-卤代-1,3-恶嗪中间体的形成。

  DOI：

  10.1002/anie.201405348

文献信息

• Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions
  作者：Jarryl M. D'Oyley、Abil E. Aliev、Tom D. Sheppard

  DOI：10.1002/anie.201405348

  日期：2014.9.26

  The regioselective conversion of propargylic alcohols into previously unreported α,α‐diiodo‐β‐hydroxyketones was achieved by treatment with N‐iodosuccinimide in the presence of a gold catalyst. The corresponding α,α‐dichloro‐β‐hydroxyketones were obtained by treatment with trichloroisocyanuric acid in the absence of a catalyst. The latter reaction can be extended to other alkynols. These transformations

  通过在金催化剂存在下用 N-碘代琥珀酰亚胺处理，实现了炔丙醇区域选择性转化为先前未报道的 α,α-二碘-β-羟基酮。在无催化剂的情况下用三氯异氰尿酸处理得到相应的α,α-二氯-β-羟基酮。后一个反应可以扩展到其他炔醇。这些转化可用于制备潜在有用的卤化结构单元。初步机理研究表明，该反应涉及乙腈溶剂参与 5-卤代-1,3-恶嗪中间体的形成。
• Reactivity of in situ generated dihalomethyllithium towards dicarboxylic acid diesters and lactones: Synthetic applications
  作者：José Barluenga、Luján Llavona、Miguel Yus、José M Concellón

  DOI：10.1016/s0040-4020(01)81943-8

  日期：1991.9

  The reaction of dicarboxylic acid diesters 1, with in situ generated dihalomethyllithium (1:1.4 molar ratio) at -78-degrees-C leads, after hydrolysis, to the corresponding dihalomethylketoesters 3. The same process using an excess of the carbenoid (1:4 molar ratio) yields the expected tetrahalodiketones 5. The reaction of these carbenoids with gamma- and delta-lactones 6 at -78-degrees-C yields, after hydrolysis, 2-(dihalomethyl) gamma- or delta-lactols 7 or 8, respectively. The reaction of lactols 7 or 8 with triethylsilane or allyltrimethylsilane in the presence of BF3.OEt2 affords the corresponding substituted tetrahydrofurans or pyrans 10 or 12. The use of epsilon-caprolactone as starting material in the reaction with dihalomethyllithium leads to the corresponding 1,1-dihalo-7-hydroxy-2-heptanones.