((2-methylcyclopropyl)sulfonyl)benzene

• 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: ((2-methylcyclopropyl)sulfonyl)benzene
• 英文别名: [(1R,2R)-2-methylcyclopropyl]sulfonylbenzene
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: SKCKZPYRPHUPFF-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((2-methylcyclopropyl)sulfonyl)benzene 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 1-[(1R,2R)-1-(benzenesulfonyl)-2-methylcyclopropyl]butan-1-one
  参考文献：
  名称：

  环丙基α-磺酰基碳负离子的酰基化和羟醛型反应

  摘要：

  生成的环丙基α-磺酰基碳负离子的酰基化和醛醇缩合反应分别以高收率得到[（1R ∗，2R ∗）-6和（1R ∗，2R ∗）-8 ]，但没有形成非对映异构体。产生的碳负离子导致快速异构化，从而提供单个非对映异构体。

  DOI：

  10.1016/s0040-4020(98)00509-2
• 作为产物：
  描述：

  toluene-4-sulfonic acid 3-benzenesulfonyl-1-methylpropyl ester 在 sodium hydride 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到((2-methylcyclopropyl)sulfonyl)benzene
  参考文献：
  名称：

  Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers

  摘要：

  The new chiron (S)-6-phenylthio-2-hexanol (3) was prepared in high enantiomeric excess by baker's yeast reduction of the corresponding ketone. Enantioenriched alcohols 1, 2 and 3, prepared previously by a similar procedure, or their racemic counterparts, were transformed into ring closed compounds 5-methyl-2-(phenylthio)tetrahydrofuran (9), 6-methyl-2-(phenylthio)tetrahydropyran (10), 2-methyl-1-phenylsulfonyl cyclopropane (14), cyclobutane (15), cyclopentane (16), and a bee pheromone, (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (20). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00635-2

文献信息

• Divergent Synthesis of β-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals
  作者：Yujin Jang、Weixia Deng、Ivan S. Sprague、Vincent N. G. Lindsay

  DOI：10.1021/acs.orglett.3c01992

  日期：2023.7.21

  approach for the synthesis of challenging β-fluoroamides from readily accessible cyclopropanone equivalents is reported. Following the addition of pyrazole used here as a transient leaving group, silver-catalyzed regiospecific ring-opening fluorination of the resulting hemiaminal leads to a β-fluorinated N-acylpyrazole intermediate reactive to substitution with amines, ultimately affording β-fluoroamides

  报道了一种从易于获得的环丙酮当量合成具有挑战性的 β-氟酰胺的权宜之计。在添加吡唑作为瞬时离开基团后，银催化的所得半氨基的区域特异性开环氟化导致β-氟化 N-酰基吡唑中间体对胺类取代反应，最终得到β-氟酰胺。该工艺还可以扩展到通过分别添加醇或氢化物作为末端亲核试剂来合成β-氟酯和γ-氟醇。
• Vitamin B₁₂‐Photocatalyzed Cyclopropanation of Electron‐Deficient Alkenes Using Dichloromethane as the Methylene Source**
  作者：John Hayford G. Teye‐Kau、Mayokun J. Ayodele、Spencer P. Pitre

  DOI：10.1002/anie.202316064

  日期：2024.1.8

  We report a vitamin B12-photocatalyzed strategy for the cyclopropanation of electron-deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction has excellent functional group tolerance, is highly chemoselective, and the scope can be extended to other 1,1-dichloroalkanes for the preparation of D2-cyclopropyl and methyl-substituted cyclopropyl adducts, all of which are important

  我们报告了一种使用二氯甲烷 (CH 2 Cl 2 ) 作为亚甲基源进行缺电子烯烃环丙烷化的维生素 B 12光催化策略。该反应具有优异的官能团耐受性，化学选择性高，范围可扩展到其他1,1-二氯烷烃，用于制备D 2 -环丙基和甲基取代环丙基加合物，这些都是医学化学中重要的电子等排体。
• Synthesis of substituted tetrahydrofurans via intermolecular reactions of γ-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes
  作者：Agnieszka Brandt、Anna Wojtasiewicz、Marcin Śnieżek、Mieczysław Mąkosza

  DOI：10.1016/j.tet.2010.02.006

  日期：2010.5

  Carbanions of 3-substituted-3-chloropropyl phenyl sulfones add to carbonyl groups of aldehydes to produce aldol type adducts that undergo 1,5-intramolecular substitution giving 2,3,5-trisubstituted tetrahydrofurans. The effect of substituents in the 3-position of these sulfones on the relative rates of 1,3-intramolecular substitution of the corresponding gamma-chlorocarbanions and their intramolecular addition are disclosed. (C) 2010 Elsevier Ltd. All rights reserved.
• Tanaka, Kazuhiko; Suzuki, Hitomi, Journal of the Chemical Society. Perkin transactions I, 1992, # 16, p. 2071 - 2074
  作者：Tanaka, Kazuhiko、Suzuki, Hitomi

  DOI：——

  日期：——
• Tanikaga, Rikuhei; Shibata, Noriaki; Yoneda, Takamitsu, Journal of the Chemical Society. Perkin transactions I, 1997, # 15, p. 2253 - 2257
  作者：Tanikaga, Rikuhei、Shibata, Noriaki、Yoneda, Takamitsu

  DOI：——

  日期：——