1-(2-chloro-1-chloromethyl-ethoxy)-butane | 89796-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-chloro-1-chloromethyl-ethoxy)-butane
• 英文别名: butyl-(β,β'-dichloro-isopropyl)-ether；Butyl-(β,β'-dichlor-isopropyl)-aether；2-Butoxy-1,3-dichlor-propan；Butyl-(2-chlor-1-chlormethyl-aethyl)-aether；InChI=1/C7H14Cl2O/c1-2-3-4-10-7(5-8)6-9/h7H,2-6H2,1H；1-(1,3-dichloropropan-2-yloxy)butane
• CAS: 89796-86-1
• 化学式: C₇H₁₄Cl₂O
• 分子量: 185.094
• InChiKey: GYOHACGDQITVQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-1-chloromethyl-ethoxy)-butane 在 potassium tert-butylate 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 30.33h， 生成 2-(2-Butoxy-allyl)-2-methyl-malonic acid diethyl ester
  参考文献：
  名称：

  A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

  摘要：

  The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a >50 mmol scale.

  DOI：

  10.1021/jo980094j
• 作为产物：
  描述：

  1,3-二氯-2-(氯甲氧基)-丙烷 、 丙基氯化镁 以 乙醚 为溶剂， 反应 12.0h， 以98.6%的产率得到1-(2-chloro-1-chloromethyl-ethoxy)-butane
  参考文献：
  名称：

  A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

  摘要：

  The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72-99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a >50 mmol scale.

  DOI：

  10.1021/jo980094j

文献信息

• Mamedov,S. et al., Journal of general chemistry of the USSR, 1964, vol. 34, # 9, p. 2900 - 2905
  作者：Mamedov,S. et al.

  DOI：——

  日期：——
• Beger, J.; Schiefer, H., Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 6, p. 1039 - 1047
  作者：Beger, J.、Schiefer, H.

  DOI：——

  日期：——
• Kambara et al., Nippon Gomu Kyokaishi, 1957, vol. 30, p. 340,341
  作者：Kambara et al.

  DOI：——

  日期：——
• SHINODA, KIYONORI;YASUDA, KENSEI, BULL. CHEM. SOC. JAP., 61,(1988) N2, C. 4393-4395
  作者：SHINODA, KIYONORI、YASUDA, KENSEI

  DOI：——

  日期：——
• BEGER J.; SCHIEFFER H., J. PRAKT. CHEM., 1980, 322, NO 6, 1039-1047
  作者：BEGER J.、 SCHIEFFER H.

  DOI：——

  日期：——

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