3-氯-2-(2'-丙烯基)环己-2-烯酮 | 50314-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氯-2-(2'-丙烯基)环己-2-烯酮
• 英文名称: 3-Chloro-2-(2-propenyl)cyclohex-2-enone
• 英文别名: 2-Allyl-3-chlor-2-cyclohexen-1-on；2-Allyl-3-chlorocyclohex-2-enone；3-chloro-2-prop-2-enylcyclohex-2-en-1-one
• CAS: 50314-05-1
• 化学式: C₉H₁₁ClO
• mdl: MFCD10699513
• 分子量: 170.639
• InChiKey: OJDAOPRPHLTVQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  3-氯-2-(2'-丙烯基)环己-2-烯酮 在 正丁基锂 、 potassium carbonate 作用下， 反应 24.75h， 生成 diethyl <<3-oxo-2-(propen-2-yl)-1-cyclohexen-1-yl>methyl>phosphonate
  参考文献：
  名称：

  Reaction of Phosphonate-Stabilized Carbanions with Cyclic Enones Bearing a .beta.-Leaving Group

  摘要：

  Reaction between alpha-lithiated alkylphosphonic esters and alpha,beta-unsaturated cyclopentenones and cyclohexenones carrying a heteroatom substituent Y in the beta-position was studied. Complete chemoselectivity was observed as a function of substituent Y. For Y = OMe exclusive addition-elimination at the beta-carbon was observed, yielding alpha,beta-unsaturated delta-ketophosphonates. The beta-chloro-substituted substrates (Y = Cl) derived from cyclohexenone reacted exclusively at the carbonyl carbon, yielding (2-hydroxyalkyl)phosphonates with the retained chlorovinyl function. The alcohols, depending on the conditions, could be dehydrated to two different products. The reaction of 3-chlorocyclopent-2-en-1-one with diethyl (lithiomethyl)phosphonate occurred at the beta-carbon, but the ketophosphonate product was isolated in a stable enolic form.

  DOI：

  10.1021/jo00130a024
• 作为产物：
  描述：

  2-allylcyclohexane-1,3-dione 在 草酰氯 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以81%的产率得到3-氯-2-(2'-丙烯基)环己-2-烯酮
  参考文献：
  名称：

  Studies culminating in the total synthesis of (dl)-morphine

  摘要：

  DOI：

  10.1021/jo00255a008

文献信息

• Rearrangement in Dihydroresorcinol Derivatives. XI. Photolysis and Thermolysis of 3-Azido-2-cyclohexen-1-ones and 2-Cyclopenten-1-ones
  作者：YASUMITSU TAMURA、SHOICHI KATO、YOSHINOBU YOSHIMURA、TADASHI NISHIMURA、YASUYUKI KITA

  DOI：10.1248/cpb.22.1291

  日期：——

  Both photolysis and thermolysis of 2-alkylsubstituted 3-azido-2-cyclohexen-1-ones and -2-cyclopenten-1-ones in methanol gave mainly the α-aminoketal derivatives, although the corresponding 2-unsubstituted compounds gave the Curtius-type rearrangement products.

  在甲醇中对 2-烷基取代的 3-叠氮-2-环己烯-1-酮和-2-环戊烯-1-酮进行光解和热解，主要得到了 α-氨基酮衍生物，但相应的 2-未取代化合物得到了 Curtius 型重排产物。
• Synthesis via vinyl sulfones. 21. Total synthesis of dl-morphine
  作者：J. E. Toth、P. L. Fuchs

  DOI：10.1021/jo00379a038

  日期：1987.2
• The Alkylation of 3-Chloro-2-cyclohexenones
  作者：Patterson

  DOI：10.1080/00397919208021327

  日期：1992.7

  Procedures for the alkylation of enolate ions derived from 3-chloro-2-cyclohexenones with reactive halides have been devised which allow introduction of one or two substituents at position 6.
• The Alder-Rickert Reaction in a Synthesis of m-Chlorophenols and 4-Chloromycophenolic Acid
  作者：John W. Patterson

  DOI：10.1021/jo00108a017

  日期：1995.2

  A new synthesis of highly substituted m-chlorophenols 12 using the Alder-Rickert reaction between 1-chloro-3-(trimethylsiloxy)-1,3-cyclohexadienes 10 and activated acetylenes has been devised. This sequence has been shown to be highly regioselective when methyl propiolate is the dienophile, and the methodology has been adapted to a facile preparation of 4-chloromycophenolic acid (23).
• GESCHWEND, GUNTER;KLEMM, DIETER, Z. CHEM., 28,(1988) N 9, C. 334
  作者：GESCHWEND, GUNTER、KLEMM, DIETER

  DOI：——

  日期：——