1-硝基-3-氯丁烷 | 81668-02-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 1-硝基-3-氯丁烷
• 英文名称: 1-nitro-3-chlorobutane
• 英文别名: 3-chloro-1-nitro-butane；3-Chlor-1-nitro-butan；3-Chloro-1-nitrobutane；3-chloro-1-nitrobutane
• CAS: 81668-02-2
• 化学式: C₄H₈ClNO₂
• 分子量: 137.566
• InChiKey: QCNCQJDNQUQHAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-硝基-3-氯丁烷 、 苄基溴化镁 以 四氢呋喃 为溶剂， 以30%的产率得到(Z)-α-Phenyl-N-<1-(3-chlorobutyl)>nitrone
  参考文献：
  名称：

  Nitrones from addition of benzyl and allyl Grignard reagents to alkyl nitro compounds: chemo-, regio-, and stereoselectivity of the reaction

  摘要：

  Reaction of allyl and benzyl Grignard reagents with functionalized nitroalkanes affords nitrones in good yield. This process shows considerable chemoselectivity; carbonyl groups and other highly reactive electrophilic functions are unaffected by the reaction conditions (THF, -70-degrees-C). A mixture of regioisomers 4 and 5 is usually obtained, and the product distribution depends on the nature of the alkyl framework. An intermediate 3 is postulated, and the isomeric pair of nitrones arises, very likely through a selective syn elimination. Alpha-substituted alkyl chains give mostly conjugated products 4 while unbranched chains afford predominantly the nonconjugated nitrones 5. The 4/5 ratio can be strongly modified by using a proton source of suitable strength; trichloroacetic acid produces 4 exclusively in the reaction of nitroethane with benzyl Grignard, while 2,6-dimethylphenol affords completely the nonconjugated nitrone 5. The stereochemistry of the double bond is affected by the nature of the reagent used. Benzyl Grignard gives only Z nitrones 4 and 5; 2-butenylmagnesium chloride gives nonconjugated Z nitrones and a predominance of E isomer in the conjugated nitrone 5.

  DOI：

  10.1021/jo00048a012
• 作为产物：
  描述：

  1-硝基丁烷 在 phosphorus pentoxide 、 氯 作用下， 生成 1-硝基-3-氯丁烷 、 1-氯-4-硝基丁烷
  参考文献：
  名称：

  The ???Butterfly??? Graft in Functional Secondary Rhinoplasty

  摘要：

  AbstractObjective To describe a surgical technique (the conchal cartilage “butterfly” graft) which, when used in properly selected patients, has been found to be a dependable method for alleviation of postrhinoplasty internal nasal valve dysfunction.Study Design Retrospective chart review.Methods Analysis of consecutive patients with weakness and/or collapse of the upper lateral cartilages following rhinoplasty. Seventy‐two patients (37 women and 35 men, age range 17–76 y) had severe nasal obstruction and were found to have indications for this procedure. All patients had undergone at least one rhinoplastic procedure. All patients were followed for a minimum of 2 years after surgery.Results All 72 patients experienced significant subjective improvement in relative nasal obstruction. Two patients (3%) reported less than total resolution of their difficulty breathing through their nose; the remaining 70 patients (97%) reported complete resolution of their nasal airway problems. No patients reported their postoperative nasal obstruction as the same or worse than their preoperative baseline. Sixty‐two patients (86%) reported improvement in the appearance of their nose, 8 patients (11%) felt that their appearance was unchanged, and 2 patients (3%) felt that the appearance of their nose was made worse by the procedure.Conclusions Patients presenting with nasal obstruction after rhinoplasty are frequently found to have collapse and/or weakening of their upper lateral cartilages with resulting nasal valve dysfunction. The conchal cartilage “butterfly” graft is a technique which, when properly performed during revision rhinoplasty, yields predictable functional and cosmetic results with minimal morbidity.

  DOI：

  10.1097/00005537-200211000-00002

文献信息

• Dneprovskii, A. S.; Mil'tsov, S. A.; Arbuzov, P. V., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 10, p. 1826 - 1835
  作者：Dneprovskii, A. S.、Mil'tsov, S. A.、Arbuzov, P. V.

  DOI：——

  日期：——
• Saeed-y-Atto; Potter, Alan; Singh, Hari, Journal of the Chemical Society. Perkin transactions II, 1982, p. 139 - 142
  作者：Saeed-y-Atto、Potter, Alan、Singh, Hari、Tedder, John M.

  DOI：——

  日期：——
• Nitrones from addition of benzyl and allyl Grignard reagents to alkyl nitro compounds: chemo-, regio-, and stereoselectivity of the reaction
  作者：Giuseppe Bartoli、Enrico Marcantoni、Marino Petrini

  DOI：10.1021/jo00048a012

  日期：1992.10

  Reaction of allyl and benzyl Grignard reagents with functionalized nitroalkanes affords nitrones in good yield. This process shows considerable chemoselectivity; carbonyl groups and other highly reactive electrophilic functions are unaffected by the reaction conditions (THF, -70-degrees-C). A mixture of regioisomers 4 and 5 is usually obtained, and the product distribution depends on the nature of the alkyl framework. An intermediate 3 is postulated, and the isomeric pair of nitrones arises, very likely through a selective syn elimination. Alpha-substituted alkyl chains give mostly conjugated products 4 while unbranched chains afford predominantly the nonconjugated nitrones 5. The 4/5 ratio can be strongly modified by using a proton source of suitable strength; trichloroacetic acid produces 4 exclusively in the reaction of nitroethane with benzyl Grignard, while 2,6-dimethylphenol affords completely the nonconjugated nitrone 5. The stereochemistry of the double bond is affected by the nature of the reagent used. Benzyl Grignard gives only Z nitrones 4 and 5; 2-butenylmagnesium chloride gives nonconjugated Z nitrones and a predominance of E isomer in the conjugated nitrone 5.
• The ???Butterfly??? Graft in Functional Secondary Rhinoplasty
  作者：J. Madison Clark、Ted A. Cook

  DOI：10.1097/00005537-200211000-00002

  日期：2002.11

  AbstractObjective To describe a surgical technique (the conchal cartilage “butterfly” graft) which, when used in properly selected patients, has been found to be a dependable method for alleviation of postrhinoplasty internal nasal valve dysfunction.Study Design Retrospective chart review.Methods Analysis of consecutive patients with weakness and/or collapse of the upper lateral cartilages following rhinoplasty. Seventy‐two patients (37 women and 35 men, age range 17–76 y) had severe nasal obstruction and were found to have indications for this procedure. All patients had undergone at least one rhinoplastic procedure. All patients were followed for a minimum of 2 years after surgery.Results All 72 patients experienced significant subjective improvement in relative nasal obstruction. Two patients (3%) reported less than total resolution of their difficulty breathing through their nose; the remaining 70 patients (97%) reported complete resolution of their nasal airway problems. No patients reported their postoperative nasal obstruction as the same or worse than their preoperative baseline. Sixty‐two patients (86%) reported improvement in the appearance of their nose, 8 patients (11%) felt that their appearance was unchanged, and 2 patients (3%) felt that the appearance of their nose was made worse by the procedure.Conclusions Patients presenting with nasal obstruction after rhinoplasty are frequently found to have collapse and/or weakening of their upper lateral cartilages with resulting nasal valve dysfunction. The conchal cartilage “butterfly” graft is a technique which, when properly performed during revision rhinoplasty, yields predictable functional and cosmetic results with minimal morbidity.