(3-hydroxyphenyl)methyl 2-nitrobenzenesulfenate | 134390-31-1

• 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: (3-hydroxyphenyl)methyl 2-nitrobenzenesulfenate
• 英文别名: 3-[(2-Nitrophenyl)sulfanyloxymethyl]phenol
• CAS: 134390-31-1
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: OOQLHRQZISYCMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-hydroxyphenyl)methyl 2-nitrobenzenesulfenate 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以74%的产率得到3-羟基苯甲醇
  参考文献：
  名称：

  (Nitroaryl)sulfinyl-substituted allenes. Novel and convenient propargyl alcohol synthons in 4 + 2 cycloaddition chemistry

  摘要：

  (Nitroaryl)sulfinyl-substituted allenes are conveniently prepared by treating propargyl alcohol or methyl 3-hydroxy-2-butynoate with a (nitroaryl)sulfenyl chloride and triethylamine. These activated allenes undergo 4 + 2 cycloaddition across the C1C2-pi-bond. The initially formed allylic sulfoxide readily undergoes a 2,3-sigmatropic rearrangement to produce a stable sulfenate ester that is easily cleaved with thiophilic reagents. The dienophilic reactivity of the (nitroary)sulfinyl-substituted allene is much greater than the corresponding propargyl alcohol, and the cycloaddition also proceeds with high regioselectivity. The Diels-Alder reaction of [(2-nitrophenyl)-sulfinyl]propadiene with Danishefsky's diene affords meta-substituted benzyl alcohols in high yield. Reaction of the more highly activated methyl 2-[(2-nitrophenyl)sulfinyl]-2,3-butadienoate with Danishefsky's diene followed by treatment of the resulting sulfenate ester with triethyl phosphite produces substituted phthalides in excellent yield. The (2,4-dinitrophenyl)sulfinyl-substituted allene was found to react smoothly with a variety of nitrones to give sulfenate esters of isoxazolidines. These allenyl sulfoxides correspond to formal equivalents of propargyl alcohol, which itself is too unreactive to undergo Diels-Alder chemistry or 1,3-dipolar cycloaddition with nitrones or nitrile oxides.

  DOI：

  10.1021/jo00013a033
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 <(2-nitrophenyl)sulfinyl>-1,2-propadiene 以 甲苯 为溶剂， 反应 12.0h， 以78%的产率得到(3-hydroxyphenyl)methyl 2-nitrobenzenesulfenate
  参考文献：
  名称：

  (Nitroaryl)sulfinyl-substituted allenes. Novel and convenient propargyl alcohol synthons in 4 + 2 cycloaddition chemistry

  摘要：

  (Nitroaryl)sulfinyl-substituted allenes are conveniently prepared by treating propargyl alcohol or methyl 3-hydroxy-2-butynoate with a (nitroaryl)sulfenyl chloride and triethylamine. These activated allenes undergo 4 + 2 cycloaddition across the C1C2-pi-bond. The initially formed allylic sulfoxide readily undergoes a 2,3-sigmatropic rearrangement to produce a stable sulfenate ester that is easily cleaved with thiophilic reagents. The dienophilic reactivity of the (nitroary)sulfinyl-substituted allene is much greater than the corresponding propargyl alcohol, and the cycloaddition also proceeds with high regioselectivity. The Diels-Alder reaction of [(2-nitrophenyl)-sulfinyl]propadiene with Danishefsky's diene affords meta-substituted benzyl alcohols in high yield. Reaction of the more highly activated methyl 2-[(2-nitrophenyl)sulfinyl]-2,3-butadienoate with Danishefsky's diene followed by treatment of the resulting sulfenate ester with triethyl phosphite produces substituted phthalides in excellent yield. The (2,4-dinitrophenyl)sulfinyl-substituted allene was found to react smoothly with a variety of nitrones to give sulfenate esters of isoxazolidines. These allenyl sulfoxides correspond to formal equivalents of propargyl alcohol, which itself is too unreactive to undergo Diels-Alder chemistry or 1,3-dipolar cycloaddition with nitrones or nitrile oxides.

  DOI：

  10.1021/jo00013a033

文献信息

• Verfahren zur Herstellung von 3-Hydroxybenzylalkohol
  申请人：BAYER AG

  公开号：EP1186587A1

  公开（公告）日：2002-03-13

  3-Hydroxybenzylalkohol kann auf einfache und kostengünstige Weise hergestellt werden, wenn man (3-Chlormethylphenyl)-chlorformiat mit einer Carbonsäure und/oder einem Carbonsäuresalz einer Acidolyse unterwirft und anschließend mit dem Reaktionsprodukt dieser ersten Stufe eine Alkoholyse durchführt.

  3-羟基苄醇可以通过将(3-氯甲基苯基)-氯甲酸酯与羧酸和/或羧酸盐进行酸解反应，然后用第一阶段的反应产物进行醇解反应，从而以简单且经济的方式制备。
• PROCESS FOR PREPARING 3-HYDROXYBENZYL ALCOHOL
  申请人：——

  公开号：US20020032353A1

  公开（公告）日：2002-03-14

  3-Hydroxybenzyl alcohol can be prepared in a simple and inexpensive way by subjecting 3-chloromethylphenyl chloroformate to an acidolysis with a carboxylic acid or a carboxylic acid salt and subsequently subjecting the reaction product of the first step to an alcoholysis.

  3-羟基苯甲醇可以通过将3-氯甲基苯基氯甲酸酯与羧酸或羧酸盐进行酸解反应，然后将第一步反应产物进行醇解反应，以简单且廉价的方式制备。
• PADWA, ALBERT;BULLOCK, WILLIAM H.;NORMAN, BRYAN H.;PERUMATTAM, JOHN, J. ORG. CHEM., 56,(1991) N3, C. 4252-4259
  作者：PADWA, ALBERT、BULLOCK, WILLIAM H.、NORMAN, BRYAN H.、PERUMATTAM, JOHN

  DOI：——

  日期：——
• US6380441B1
  申请人：——

  公开号：US6380441B1

  公开（公告）日：2002-04-30