1-chloro-4-[(3-chloropropyl)sulfinyl]benzene | 55765-52-1

• 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-chloro-4-[(3-chloropropyl)sulfinyl]benzene
• 英文别名: 1-(p-chlorophenylsulfinyl)-3-chloropropane；1-chloro-4-(3-chloropropylsulfinyl)benzene
• CAS: 55765-52-1
• 化学式: C₉H₁₀Cl₂OS
• 分子量: 237.15
• InChiKey: MLNWOWXKWIYMIG-UHFFFAOYSA-N

物化性质

• 沸点：
  375.7±27.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• 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-chloro-4-[(3-chloropropyl)sulfinyl]benzene 在 potassium tert-butylate 、 4-氯苯甲醛 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到1-Chloro-4-cyclopropanesulfinyl-benzene
  参考文献：
  名称：

  Diastereoselective Synthesis of Tetrahydrofurans from Aryl 3-Chloropropylsulfoxides and Aldehydes

  摘要：

  Carbanions of aryl 3-chloropropylsulfoxides react with nonenolizable aldehydes to give 2,3-disubstituted tetrahydrofurans. Deprotonation of the sulfoxides carried out in the presence of aldehydes results in the addition of the carbanions to the carbonyl group of the aldehydes, followed by 1,5-intra-molecular substitution of the resulting aldol-type anion to produce the tetrahydrofuran ring. The 2-aryl and 3-arylsulfinyl substituents are always in trans relation, and the reaction proceeds with high diastereoselectivity also in respect to the chiral sulfur atom. The diastereoselectivity is attributed to the cyclic transition state of the aldol addition and increases when the aromatic ring of the sulfoxide contains electron-withdrawing substituents, whereas that of the aldehyde has eleetron-donatine groups.

  DOI：

  10.1021/jo1002196
• 作为产物：
  描述：

  1-chloro-4-[(3-chloropropyl)thio]benzene 在 水 、 溴 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到1-chloro-4-[(3-chloropropyl)sulfinyl]benzene
  参考文献：
  名称：

  Diastereoselective Synthesis of Tetrahydrofurans from Aryl 3-Chloropropylsulfoxides and Aldehydes

  摘要：

  Carbanions of aryl 3-chloropropylsulfoxides react with nonenolizable aldehydes to give 2,3-disubstituted tetrahydrofurans. Deprotonation of the sulfoxides carried out in the presence of aldehydes results in the addition of the carbanions to the carbonyl group of the aldehydes, followed by 1,5-intra-molecular substitution of the resulting aldol-type anion to produce the tetrahydrofuran ring. The 2-aryl and 3-arylsulfinyl substituents are always in trans relation, and the reaction proceeds with high diastereoselectivity also in respect to the chiral sulfur atom. The diastereoselectivity is attributed to the cyclic transition state of the aldol addition and increases when the aromatic ring of the sulfoxide contains electron-withdrawing substituents, whereas that of the aldehyde has eleetron-donatine groups.

  DOI：

  10.1021/jo1002196

文献信息

• N-substituted alpha-arylazacycloalkylmethanamines and their use as
  申请人：A. H. Robins Company Incorporated

  公开号：US05198449A1

  公开（公告）日：1993-03-30

  Novel compounds of the formula below wherein W is azetidine, pyrrolidine or piperidine, Q is a straight chain hydrocarbon radical of 1-4 carbons and may contain a double bond, and ##STR1## Ar is phenyl, pyridinyl or pyrimidinyl, a process for their preparation, and novel intermediates are disclosed. The novel compounds and the pharmaceutical compositions of this invention are useful in the treatment of hypertension, arrhythmias and angina.

  以下是该公式的新化合物，其中W为氮杂环丙烷、吡咯烷或哌嗪，Q为含有1-4个碳原子的直链烃基，可能含有双键，Ar为苯基、吡啶基或嘧啶基。公开了它们的制备方法和新型中间体。该发明的新化合物和药物组合物在治疗高血压、心律失常和心绞痛方面具有用途。
• 1-Phenylthiopropyl-4-hydroxy-4-phenyl piperidines
  申请人：Sumitomo Chemical Co., Ltd.

  公开号：US03960873A1

  公开（公告）日：1976-06-01

  Novel N-substituted heterocyclic derivatives represented by the formula, ##SPC1## Wherein R.sub.1 is hydrogen atom, lower alkyl, lower alkoxy, nitro, halogen or trifluoromethyl group; R.sub.2 is hydrogen atom or lower alkyl group; X is sulfur atom, sulfinyl or sulfonyl group; Y is ##EQU1## group (wherein R.sub.3 is phenyl or substituted phenyl group; R.sub.4 is hydrogen atom, hydroxy, lower alkyl, lower alkoxy, lower alkanoyl, lower alkanoyloxy, carbamoyl, N-(lower alkyl)-carbamoyl or N,N-di(lower akyl)-carbamoyl group; R.sub.5 is hydrogen atom, morpholino, pyrrolidinyl, piperidinyl, hexamethylenimino, lower alkyl, cyclo(lower alkyl), cyclo(lower alkyl)-(lower alkyl), hydroxy-(lower alkyl), (lower alkoxy)-(lower alkyl), phenyl or substituted phenyl group; k is 0 or 1 and m is 0, 1 or 2); and n is 3 or 4, and pharmaceutically acceptable salts thereof, which have excellent tranquillizing, anti-psychotonic, anti-emotional, anti-convulsive, anti-psychosis, sedative, analgesic or anti-hypertensive activities.

  由以下公式表示的新型N-取代杂环衍生物：##SPC1## 其中R.sub.1为氢原子、低烷基、低烷氧基、硝基、卤素或三氟甲基基团；R.sub.2为氢原子或低烷基基团；X为硫原子、亚硫基或磺酰基团；Y为##EQU1##基团（其中R.sub.3为苯基或取代苯基基团；R.sub.4为氢原子、羟基、低烷基、低烷氧基、低烷酰基、低烷酰氧基、氨甲酰基、N-(低烷基)-氨甲酰基或N,N-二(低烷基)-氨甲酰基；R.sub.5为氢原子、吗啡啉基、吡咯啉基、哌啶基、己亚甲基氨基、低烷基、环烷基、环烷基-(低烷基)、羟基-(低烷基)、(低烷氧基)-(低烷基)、苯基或取代苯基基团；k为0或1，m为0、1或2）；n为3或4，及其药学上可接受的盐，具有出色的镇静、抗精神病、抗情绪、抗抽搐、抗精神病、镇静、镇痛或降压活性。
• US3960873A
  申请人：——

  公开号：US3960873A

  公开（公告）日：1976-06-01
• US5198449A
  申请人：——

  公开号：US5198449A

  公开（公告）日：1993-03-30
• Diastereoselective Synthesis of Tetrahydrofurans from Aryl 3-Chloropropylsulfoxides and Aldehydes
  作者：Zofia Komsta、Michał Barbasiewicz、Mieczysław Ma̧kosza

  DOI：10.1021/jo1002196

  日期：2010.5.21

  Carbanions of aryl 3-chloropropylsulfoxides react with nonenolizable aldehydes to give 2,3-disubstituted tetrahydrofurans. Deprotonation of the sulfoxides carried out in the presence of aldehydes results in the addition of the carbanions to the carbonyl group of the aldehydes, followed by 1,5-intra-molecular substitution of the resulting aldol-type anion to produce the tetrahydrofuran ring. The 2-aryl and 3-arylsulfinyl substituents are always in trans relation, and the reaction proceeds with high diastereoselectivity also in respect to the chiral sulfur atom. The diastereoselectivity is attributed to the cyclic transition state of the aldol addition and increases when the aromatic ring of the sulfoxide contains electron-withdrawing substituents, whereas that of the aldehyde has eleetron-donatine groups.