2-methyl-2-phenylcarbamylmethyl-1,3-oxathiolane | 67980-06-7

• 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-methyl-2-phenylcarbamylmethyl-1,3-oxathiolane
• 英文别名: 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide；α-(2-methyl-1,3-oxathiolan-2-yl)acetanilide；2-methyl-N-phenyl-1,3-oxathiolane-2-acetoamide；2-methyl-N-phenyl-1,3-oxatiolane-2-acetamide；1,3-Oxathiolane-2-acetamide, 2-methyl-N-phenyl-；2-(2-methyl-1,3-oxathiolan-2-yl)-N-phenylacetamide
• CAS: 67980-06-7
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: NQIICSBSMAOADW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2-phenylcarbamylmethyl-1,3-oxathiolane 在 双氧水 、 对甲苯磺酸 、 溶剂黄146 作用下， 反应 39.5h， 生成 N-乙酰乙酰苯胺
  参考文献：
  名称：

  Synthesis of dihydro-1,4-oxathiins by rearrangement of 1,3-oxathiolane sulfoxides

  摘要：

  DOI：

  10.1021/jo00364a033
• 作为产物：
  描述：

  (E)-3-{2-[2-((E)-1-Methyl-2-phenylcarbamoyl-vinyloxy)-ethyldisulfanyl]-ethoxy}-but-2-enoic acid phenylamide 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 苯 为溶剂， 反应 38.55h， 生成 2-methyl-2-phenylcarbamylmethyl-1,3-oxathiolane
  参考文献：
  名称：

  Synthesis of dihydro-1,4-oxathiins by rearrangement of 1,3-oxathiolane sulfoxides

  摘要：

  DOI：

  10.1021/jo00364a033

文献信息

• Synthesis of 1,3-oxathiolane sulfoxide compounds
  申请人：Uniroyal Chemical Ltd./Ltee

  公开号：US05654441A1

  公开（公告）日：1997-08-05

  A process for the production of a 1,3-oxathiolane sulfoxide of the formula ##STR1## wherein X is an amino group of the formula --NHR, wherein R is hydrogen, phenyl, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, nitrophenyl, (C.sub.1 -C.sub.4 alkoxy)phenyl, furfuryl, halophenyl, tolyl, napthyl, biphenyl or hydroxyphenyl; or X is an alkoxy group of the formula --OR.sup.1 wherein R is C.sub.1 -C.sub.6 alkyl, which process comprises oxidizing a 1,3-oxathiolane of the formula ##STR2## wherein X is as defined above, in the presence of an effective amount of aqueous hydrogen peroxide and a sterically-hindered organoselenium compound of the formula ##STR3## wherein R.sup.2 is aryl, mono-, di- or tri-substituted with C.sub.1 -C.sub.3 alkyl, to the produce the 1,3-oxathiolane sulfoxide. This process stereoselectively produces the cis stereoisomer of the 1,3-oxathiolane sulfoxide. Additionally, there is disclosed a novel method for the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin compounds using this process.

  一种用于生产1,3-氧硫环戊烷亚氧化物的过程，其分子式为##STR1##其中X是分子式--NHR的氨基团，其中R是氢、苯基、C.sub.1 -C.sub.8烷基、C.sub.3 -C.sub.6环烷基、硝基苯基、(C.sub.1 -C.sub.4烷氧基)苯基、呋喃基、卤代苯基、甲苯基、萘基、联苯基或羟基苯基；或X是分子式--OR.sup.1的烷氧基，其中R是C.sub.1 -C.sub.6烷基，该过程包括在有效量的水过氧化氢和一种具有立体位阻的有机硒化合物的存在下氧化分子式为##STR2##其中X如上定义的1,3-氧硫环戊烷，以产生1,3-氧硫环戊烷亚氧化物。该过程立体选择性地产生1,3-氧硫环戊烷亚氧化物的顺式异构体。此外，还公开了一种使用该过程制备5,6-二氢-2-甲基-1,4-氧硫环丙烷化合物的新方法。
• Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide
  申请人：Uniroyal, Ltd.

  公开号：US04182716A1

  公开（公告）日：1980-01-08

  This method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide is based on the use of an oxathiolane, namely, 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide, which may be formed by condensing 2-mercaptoethanol with acetoacetanilide under acidic conditions in a solvent medium (aromatic hydrocarbon, chlorinated hydrocarbon or alkyl ester of an aliphatic acid). The said oxathiolane, with or without purification, is reacted with hydrogen peroxide in water or in a water-organic solvent mixture under basic conditions in the presence of a catalytic amount of a metal compound such as sodium tungstate to form 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide 3-oxide. The said oxathiolane oxide, while dissolved in a chlorinated hydrocarbon or an alkyl ester of an aliphatic carboxylic acid, or while suspended in an aromatic hydrocarbon, is subjected to a ring expansion reaction by heating under acidic conditions in the presence of a catalytic quantity of a quaternary ammonium salt to form 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide with evolution of water. The product is a known bactericide and fungicide.

  制备5,6-二氢-2-甲基-N-苯基-1,4-噁嗪-3-羧酰胺的方法基于使用一种噁硫环，即2-甲基-N-苯基-1,3-噁硫环-2-乙酰胺，该噁硫环可以通过在溶剂介质（芳香烃、氯化烃或脂肪酸烷基酯）中在酸性条件下将2-巯基乙醇与乙酰苯胺缩合而成。该噁硫环，经过纯化或未经纯化，与过氧化氢在水或水-有机溶剂混合物中在碱性条件下，在钨酸钠等金属化合物的催化作用下反应，形成2-甲基-N-苯基-1,3-噁硫环-2-乙酰胺3-氧化物。该噁硫环氧化物，在氯化烃或脂肪族羧酸酯的溶剂中溶解或在芳香烃中悬浮，经过在酸性条件下在季铵盐的催化作用下加热环扩张反应，生成5,6-二氢-2-甲基-N-苯基-1,4-噁嗪-3-羧酰胺，并放出水。该产品是一种已知的杀菌剂和杀真菌剂。
• Nevalainen, Vesa; Pohjala, Esko, Journal of Chemical Research, Miniprint, 1988, # 6, p. 1401 - 1421
  作者：Nevalainen, Vesa、Pohjala, Esko

  DOI：——

  日期：——
• Synthesis of dihydro-1,4-oxathiins by action of chlorine on 1,3-oxathiolanes
  作者：Wha Suk Lee、Oee Sook Park、Joong Kwon Choi、Kee Dal Nam

  DOI：10.1021/jo00233a012

  日期：1987.11
• Hahn, Hoh-Gyu; Lee, Wha Suk, Journal of Chemical Research, Miniprint, 1995, # 3, p. 630 - 645
  作者：Hahn, Hoh-Gyu、Lee, Wha Suk

  DOI：——

  日期：——