S-3-methyl-2-pyridyl propanethioate | 146347-49-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-3-methyl-2-pyridyl propanethioate
• 英文别名: 2-propionylthio-3-methyl pyridine；2-Propionylthio-3-methylpyridine；S-(3-methylpyridin-2-yl) propanethioate
• CAS: 146347-49-1
• 化学式: C₉H₁₁NOS
• 分子量: 181.258
• InChiKey: LJVMBFXOZRSEOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-亚苄基-4-甲氧基苯胺 、 S-3-methyl-2-pyridyl propanethioate 在 四氯化钛 、 三乙胺 作用下， 生成 trans-1-(4-methoxyphenyl)-3-methyl-4-phenylazetidin-2-one 、 syn-1-(p-methoxyphenyl)-3-methyl-4-phenylazetidin-2-one
  参考文献：
  名称：

  Annunziata, Rita; Cinquini, Mauro; Cozzi, Franco, Gazzetta Chimica Italiana, 1993, vol. 123, # 4, p. 181 - 184

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 在 tetraphosphorus decasulfide 、 硫酸 、 三乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 生成 S-3-methyl-2-pyridyl propanethioate
  参考文献：
  名称：

  Versatile Synthesis of an Intermediate for the 1b-Methylcarbapenem Synthesis

  摘要：

  A 1 beta-Methylcarboxylate (1) which is a requisite intermediate for the synthesis of the 1 beta-methylcarbapenem was obtained in an efficient manner by the coupling reaction of a Z(O)-pyridylthiosilyl enol ether and a 4-acetoxyazetidinone derivative in the presence of ZnCl2 in CH2Cl2. The reactive silyl enol ether was prepared by the reverse addition method in high yield.

  DOI：

  10.3987/com-93-6603

文献信息

• Azetidinone compounds useful in the preparation of carbapenem
  申请人：Sankyo Company, Limited

  公开号：US05541317A1

  公开（公告）日：1996-07-30

  Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; is R.sup.4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.

  化合物的化学式（I）：##STR1##其中：R.sup.1是氢或羟基保护基；R.sup.2是烷基，烷氧基，卤素，可选择取代的苯基或可选择取代的苯氧基；R.sup.3是可选择取代的吡啶基，可选择取代的喹啉基或带有化学式--CYNR.sup.5 R.sup.6的苯基，其中Y为氧或硫，R.sup.5和R.sup.6分别为烷基，芳基或芳基烷基，或R.sup.5和R.sup.6以及它们连接的氮共同形成杂环基；R.sup.4为氢或氨基保护基；Z为硫或氧；在头孢内酯类化合物的制备中是有价值的中间体，并在转化为这类头孢内酯类化合物时保持理想的构型。具有化学式--SA'的头孢内酯和头孢内酯类化合物是通过将在该位置具有取代硫，亚硫酰基或磺酰基团的相应化合物与存在于周期表第II或III族金属盐的存在下与化合物A'SH（其中A'为有机基）反应制备的。
• Carbapenem
  申请人：Sankyo Company, Limited

  公开号：US05614624A1

  公开（公告）日：1997-03-25

  A compound of the formula ##STR1## in which: R.sup.1' is hydrogen or a carboxy-protecting group; R.sup.41' is hydrogen or a hydroxy-protecting group; R.sup.42' is a C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 alkoxy, a halogen, an aryl or an aryloxy; R.sup.43' is hydrogen, a C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 alkoxy, a hydroxy, a halogen, a cyano, a nitro or a group of the formula --NR.sup.8' R.sup.9', where R.sup.8' and R.sup.9' are independently selected from the group consisting of hydrogen, amino-protecting groups, C.sub.1 -C.sub.6 alkyl groups and phenyl groups, or R.sup.8' and R.sup.9' together represent a group --(CH.sub.2).sub.q '--O.sub.r '--(CH.sub.2).sub.s '--, where q' and s' are independently 0 or an integer of from 1 to 5 and r' is 0 or 1, provided that (q'+s') is an integer of at least 2; R.sup.45' and R.sup.46' are independently selected from the group consisting of C.sub.1 -C.sub.6 alkyl groups and aryl groups, or R.sup.45' and R.sup.46' together represent a group --(CH.sub.2).sub.q '--O.sub.r '--(CH.sub.2).sub.s '--, where q' and s' are independently 0 or an integer of from 1 to 5 and r' is 0 or 1; Y' is oxygen or sulfur; and j' is 0, 1 or 2.

  该化合物的结构式为##STR1##其中：R.sup.1'为氢或羧基保护基；R.sup.41'为氢或羟基保护基；R.sup.42'为C.sub.1-C.sub.6烷基，C.sub.1-C.sub.6烷氧基，卤素，芳基或芳氧基；R.sup.43'为氢，C.sub.1-C.sub.6烷基，C.sub.1-C.sub.6烷氧基，羟基，卤素，氰基，硝基或式--NR.sup.8'R.sup.9'的基团，其中R.sup.8'和R.sup.9'独立地选择自羟基保护基，C.sub.1-C.sub.6烷基和苯基的群，或R.sup.8'和R.sup.9'在一起表示式--(CH.sub.2).sub.q '--O.sub.r '--(CH.sub.2).sub.s '--的基团，其中q'和s'独立地为0或从1到5的整数，r'为0或1，前提是(q'+s')至少为2的整数；R.sup.45'和R.sup.46'独立地选择自C.sub.1-C.sub.6烷基和芳基，或R.sup.45'和R.sup.46'在一起表示式--(CH.sub.2).sub.q '--O.sub.r '--(CH.sub.2).sub.s '--的基团，其中q'和s'独立地为0或从1到5的整数，r'为0或1；Y'为氧或硫；j'为0、1或2。
• Metal catalyzed displacement process
  申请人：Sankyo Company, Limited

  公开号：US05681951A1

  公开（公告）日：1997-10-28

  A process for preparing a compound of formula (I'): ##STR1## comprising reacting a compound of formula (II'): ##STR2## with a compound of formula (III'): A'SH (III') wherein the reaction of the compound of formula (II') and the compound of formula (III') are carried out in the presence of a salt of a metal of Group II or III of the Periodic Table of Elements, wherein A' is an alkyl, aryl, aralkyl or heterocyclic, R.sup.1' is hydrogen or a carboxy protecting group, R.sup.2' and R.sup.3' can be hydrogen or alkyl, X' can be sulfur, k' is 1 or 2 and R.sup.4' is alkyl, alkenyl, aryl, aralkyl, cycloalkyl or heterocyclic.

  一种制备式（I'）化合物的方法： ##STR1## 包括将式（II'）化合物与式（III'）化合物反应： ##STR2## 其中化合物（II'）和化合物（III'）的反应在元素周期表II或III族金属的盐的存在下进行，其中A'是烷基，芳基，芳烷基或杂环基，R.sup.1'是氢或羧基保护基，R.sup.2'和R.sup.3'可以是氢或烷基，X'可以是硫，k'为1或2，R.sup.4'是烷基，烯基，芳基，芳烷基，环烷基或杂环基。
• Silyl enol ether alkylation process
  申请人：Sankyo Company, Limited

  公开号：US05719275A1

  公开（公告）日：1998-02-17

  A method for preparing compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; R.sup.4 is hydrogen or an amino-protecting group; and Z is sulfur or oxygen. The process comprises reacting a compound of formula (II): ##STR2## in which R.sup.8, R.sup.9 and R.sup.10 are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or a phenyl group, with a compound of formula (III): ##STR3## in which R.sup.11 represents an acyloxy, alkylsulfonyl, arylsulfonyl, alkylsulfinyl or arylsulfinyl group.

  一种制备式（I）化合物的方法：其中：R.sup.1是氢或羟基保护基；R.sup.2是烷基，烷氧基，卤素，可选地取代的苯基或可选地取代的苯氧基；R.sup.3是可选地取代的吡啶基，可选地取代的喹啉基或具有式--CYNR.sup.5 R.sup.6的取代基的苯基，其中Y是氧或硫，R.sup.5和R.sup.6分别是烷基，芳基或芳烷基，或R.sup.5和R.sup.6和它们所连接的氮共同形成一个杂环基；R.sup.4是氢或氨基保护基；Z是硫或氧。该过程包括将式（II）的化合物与式（III）的化合物反应：其中R.sup.8，R.sup.9和R.sup.10相同或不同，每个代表具有1至4个碳原子的烷基或苯基。其中，式（II）为：##STR2##式（III）为：##STR3##
• Azetidinone derivatives useful in the preparation of carbapenem antibiotics
  申请人：Sankyo Company Limited

  公开号：EP0516486B1

  公开（公告）日：2000-12-20