1,1-二氯-2-乙氧基环丙烷 | 7363-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1-二氯-2-乙氧基环丙烷
• 英文名称: 1,1-dichloro-2-ethoxycyclopropane
• 英文别名: 1,1-dichloro-2-ethoxy-cyclopropane；ethyl-(2,2-dichloro-cyclopropyl)-ether；Aethyl-(2,2-dichlor-cyclopropyl)-aether
• CAS: 7363-99-7
• 化学式: C₅H₈Cl₂O
• 分子量: 155.024
• InChiKey: CFGDPDUZPQLEGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  1,1-二氯-2-乙氧基环丙烷 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以66%的产率得到2-chloroprop-2-enal diethyl acetal
  参考文献：
  名称：

  Multivariate Optimization of a Cyclopropanation, the Key Step in the Synthesis of 3,3,4,4-Tetraethoxybut-1-yne

  摘要：

  3,3,4,4-Tetraethoxybut-1-yne (TEB) is a versatile syntbon that can be produced in a four-step synthesis. The third step of the synthesis is a cycloproanation, which has been thoroughly investigated and optimized by means of statistical experimental design and multivariate modeling. At the outset, an exhaustively pre-experimental design was performed resulting in a copious Ishikawa cause-effect diagram. In total six of the experimental variables were assessed to be of large importance and thus selected for further investigation by fractional factorial design. The results of that screening and first step optimization formed the basis for a response surface modeling (RSM) study. The RSM investigation was completed by using a central composite design from which a response surface was graphically produced as an iso-contour projection. The derived multivariate predictive model in terms the iso-contour projection plots were ultimately utilized to establish experimental conditions that concomitantly provided excellent yield (>99%) and minimized amounts of inputs and thus obtain the desired product at the lowest production cost and minimized side-streams.

  DOI：

  10.1021/op5001012
• 作为产物：
  描述：

  乙烯基乙醚 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 反应 24.17h， 以84%的产率得到1,1-二氯-2-乙氧基环丙烷
  参考文献：
  名称：

  SYNTHESIS OF 2-CHLOROACROLEIN DIETHYL ACETAL

  摘要：

  DOI：

  10.15227/orgsyn.083.0184

文献信息

• Generation and Trapping of Cyclopropenes from 2-Alkoxy-1,1-dichlorocyclopropanes
  作者：Paul Müller、Nicole Pautex

  DOI：10.1002/hlca.19910740108

  日期：1991.1.30

  In presence of crown ether, 2-alkoxy-1,1-dichlorocyclopropanes react with t-BuOK/THF preferentially via ring opening to 2-chloroalk-2-en-1-ones and alkynones or to chlorocyclopropenes. The latter may be intercepted with 1,3-diphenylisobenzofuran, but in the absence of trapping agent, the rearrangement to vinylcarbenes does not occur.

  在冠醚的存在下，2-烷氧基-1，1-二氯环丙烷优选通过开环与t - BuOK / THF反应成2-氯烷基-2-烯-1-酮和炔酮或成氯环丙烯。后者可能被1,3-二苯基异苯并呋喃所拦截，但是在没有捕集剂的情况下，不会发生向乙烯基碳烯的重排。
• Dahl,H. et al., Justus Liebigs Annalen der Chemie, 1972, vol. 755, p. 40 - 50
  作者：Dahl,H. et al.

  DOI：——

  日期：——
• The Electron-seeking Demands of Dichlorocarbene in its Addition to Olefins
  作者：W. von E. Doering、Wm. A. Henderson

  DOI：10.1021/ja01552a065

  日期：1958.10
• Nerdel,F. et al., Justus Liebigs Annalen der Chemie, 1967, vol. 710, p. 36 - 58
  作者：Nerdel,F. et al.

  DOI：——

  日期：——
• Synthesis and biological activity of gem-dichlorocyclopropyl ethers
  作者：S. M. Shostakovskii、V. N. Mochalov、G. M. Larionov

  DOI：10.1007/bf00766631

  日期：1985.11