1-chlorocyclopropyl phenyl sulfoxide | 65006-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-chlorocyclopropyl phenyl sulfoxide
• 英文别名: [(1-Chlorocyclopropyl)sulfinyl]benzene；(1-chlorocyclopropyl)sulfinylbenzene
• CAS: 65006-97-5
• 化学式: C₉H₉ClOS
• 分子量: 200.689
• InChiKey: SOZLZFHVVDEWNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chlorocyclopropyl phenyl sulfoxide 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  A novel synthesis of spiro[2.6]nonadienones by the reaction of magnesium cyclopropylidenes with naphtholates and phenolates

  摘要：

  The sulfoxide-magnesium exchange reaction of aryl 1-chlorocyclopropyl sulfoxides with i-PrMgCl in THF at low temperature gave magnesium cyclopropylidenes. Treatment of the magnesium cyclopropylidenes with lithium naphtholates or phenolates resulted in the formation of spiro[2.6]nonadienones in up to 82% yield. The structure of the spiro[2.6]nonadienones was found to be dependent on the structure of the naphtholates and phenolates. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.066
• 作为产物：
  描述：

  cyclopropyl phenyl sulfoxide 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 生成 1-chlorocyclopropyl phenyl sulfoxide
  参考文献：
  名称：

  基于环亚丙基镁与α-磺酰基碳负离子反应的亚烷基环丙烷的合成新方法

  摘要：

  在低温下用异丙基氯化镁处理1-氯环丙基苯基亚砜，得到环亚丙基镁。发现产生的类胡萝卜素与α-磺酰基碳负离子锂的反应以中等至良好的产率提供了亚烷基环丙烷。该反应提供了一种新颖，前所未有，用途广泛的方法，可以在较短的时间内由烯烃合成几种亚烷基环丙烷。

  DOI：

  10.1016/j.tetlet.2003.10.162

文献信息

• A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids
  作者：Serena Monticelli、Ernst Urban、Thierry Langer、Wolfgang Holzer、Vittorio Pace

  DOI：10.1002/adsc.201801614

  日期：2019.3.5

  homologation of carbon dioxide with stable, (enantiopure) magnesium carbenoids constitutes a valuable method for preparing α‐halo acid derivatives. The tactic features a high level of chemocontrol, thus enabling the synthesis of variously functionalized analogues. The flexibility to generate magnesium carbenoids through sulfoxide‐, halogen‐ or proton‐ Mg exchange accounts for the wide scope of the reaction.

  二氧化碳与稳定的（对映纯）镁类胡萝卜素的同系物构成制备α-卤代酸衍生物的一种有价值的方法。该策略具有高水平的化学控制功能，因此可以合成各种功能化的类似物。通过亚砜，卤素或质子镁交换生成镁类胡萝卜素的灵活性，说明了反应的广泛性。
• Synthesis of Spiro[2.6]nonadienones and Spiro[3.6]decadienones by the Reaction of Cyclopropyl- and Cyclobutylmagnesium Carbenoids with Lithium Phenolates and Naphtholates
  作者：Tsuyoshi Satoh、Tsutomu Kimura、Yuki Sasaki、Shinobu Nagamoto

  DOI：10.1055/s-0031-1291011

  日期：2012.7

  spiro[2.6]nona-5,7-dien-4-ones in moderate to good yields; however, reaction of the cyclobutylmagnesium carbenoids with lithium 1-naphtholates did not give the desired products. Reaction of the cyclopropyl- and cyclobutylmagnesium carbenoids with lithium 2-naphtholates gave spiro[2.6]nona-5,7-dien-4-ones and spiro[3.6]deca-7,9-dien-6-ones, respectively, in moderate to good yields. These unprecedented

  摘要 的1-氯治疗p -甲苯基砜和1- chlorocyclobutyl p格氏试剂在低温下与甲苯基亚砜通过亚砜-镁交换反应分别得到环丙基镁类胡萝卜素和环丁基镁类胡萝卜素。这些镁类化合物与酚酸锂的反应分别得到了螺[2.6] nona-6,8-dien-5-one和螺[3.6] deca-7,9-dien-6-one。但是，产量很低。环丙基镁类胡萝卜素与1-萘甲酸锂的反应以中等至良好的产率得到了螺[2.6] nona-5,7-dien-4-ones。然而，环丁基镁类胡萝卜素与1-萘甲酸锂的反应未得到所需产物。环丙基和环丁基镁的类胡萝卜素与2-萘甲酸锂的反应分别中等程度地产生了螺[2.6] nona-5,7-dien-4-one和螺[3.6] deca-7,9-dien-6-one。高产。 的1-氯治疗p -甲苯基砜和1- chlorocyclobutyl p格氏试剂在低温下与甲苯基亚砜通过亚
• Substitution of both chloro and sulfinyl groups of aryl 1-chlorocyclopropyl sulfoxides in one-pot via cyclopropylmagnesium carbenoids: a synthesis of multi-substituted cyclopropanes
  作者：Masanobu Yajima、Ryo Nonaka、Hironori Yamashita、Tsuyoshi Satoh

  DOI：10.1016/j.tetlet.2009.06.019

  日期：2009.8

  The rearrangement of cyclopropylmagnesium carbenoids, which were generated from aryl 1-chlorocyclopropyl sulfoxides with a Grignard reagent, to allenes was found to be suppressed by adding HMPA as an additive. Alkylation of the cyclopropylmagnesium carbenoids with the Grignard reagent gives mainly alkylated cyclopropylmagnesium chloride instead. The cyclopropylmagnesium chloride intermediate can be

  发现通过添加HMPA作​​为添加剂可以抑制由芳基1-氯环丙基亚砜与格氏试剂生成的环丙基镁类胡萝卜素重排至丙二烯。用格氏试剂将环丙基镁类化合物烷基化，主要得到的是烷基化的环丙基氯化镁。环丙基氯化镁中间体可以用几种亲电试剂捕集，得到多取代的环丙烷。该程序提供了一种合成多取代环丙烷的新方法。
• Synthesis of small ring-containing conjugated dienes via the coupling reaction of cyclopropyl- and cyclobutylmagnesium carbenoids with α-sulfonylallyllithiums
  作者：Tsutomu Kimura、Mio Inumaru、Takuma Migimatsu、Masashi Ishigaki、Tsuyoshi Satoh

  DOI：10.1016/j.tet.2013.03.019

  日期：2013.5

  synthesized via the coupling reaction of cyclopropyl- and cyclobutylmagnesium carbenoids with α-sulfonylallyllithiums. Small ring cycloalkylmagnesium carbenoids were generated from aryl 1-chlorocycloalkyl sulfoxides and a Grignard reagent, and the resultant magnesium carbenoids were reacted with α-sulfonylallyllithiums, which were prepared via the deprotonation of p-tolyl vinyl sulfones or allyl p-tolyl

  通过环丙基和环丁基镁类胡萝卜素与α-磺酰基烯丙基锂的偶联反应，合成了各种烯丙基环丙烷和烯丙基环丁烷。由芳基1-氯环烷基亚砜和格利雅试剂生成小环环烷基镁类胡萝卜素，然​​后使生成的镁类胡萝卜素与α-磺酰基烯丙基锂反应，后者是通过对甲苯基乙烯基砜或烯丙基p的去质子化反应制得的。-甲苯基砜。亚芳基环烷烃的收率中等至良好，而亚芳基环烷烃与四氰基乙烯的Diels-Alder反应提供了螺环化合物。无环烷基镁类胡萝卜素与α-磺酰基烯丙基锂的偶联反应提供了作为几何异构体混合物的共轭二烯。DFT计算的结果表明，相对于相应的氯环烷烃，小环环烷基镁类胡萝卜素具有较长的C–Cl键，并且C–Cl键的背面具有扩展的键角。
• Insertion of cyclopropanes between a carbonyl carbon and an α-carbon of carbonyl compounds with cyclopropylmagnesium carbenoids
  作者：Tsuyoshi Satoh、Gaku Kashiwamura、Shinobu Nagamoto、Yuki Sasaki、Shimpei Sugiyama

  DOI：10.1016/j.tetlet.2011.06.069

  日期：2011.8

  The reaction of the lithium enolates of α-aryl carbonyl compounds with cyclopropylmagnesium carbenoids, derived from 1-chlorocyclopropyl p-tolyl sulfoxides with i-PrMgCl at low temperature, resulted in the formation of β-aryl carbonyl compounds bearing a cyclopropane ring at the α-position with one-carbon homologation in variable yields. The reaction was found to be highly stereospecific with respect

  α-芳基羰基化合物的烯醇锂与衍生自1-氯环丙基对甲苯基亚砜的环丙基镁类胡萝卜素与i- PrMgCl在低温下反应，导致在α处形成带有环丙烷环的β-芳基羰基化合物位具有可变碳收率的一碳同系物。关于环丙基镁类胡萝卜素的立体化学，发现该反应具有高度立体特异性。还讨论了反应的立体特异性的机理和起源。这是在羰基化合物的羰基碳和α-碳之间插入环丙烷的第一个例子。