5-hydroxy-7-mercapto-2,2-dimethyl-4-chromanone | 98834-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-hydroxy-7-mercapto-2,2-dimethyl-4-chromanone
• 英文别名: 5-Hydroxy-2,2-dimethyl-7-sulfanylchroman-4-one；5-hydroxy-2,2-dimethyl-7-sulfanyl-3H-chromen-4-one
• CAS: 98834-35-6
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: BSBJNWAFSRQOGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-7-mercapto-2,2-dimethyl-4-chromanone 在 镍 作用下， 以 乙醇 为溶剂， 生成 2,2-dimethyl-5-hydroxy-4-keto-benzopyran
  参考文献：
  名称：

  Modification of Hydroxybenzopyranoids: Facile Deoxygenation of 2,2-Dimethyl-7-hydroxy-4-chromanones and a New Approach to Their Novel Mercapto Analogs

  摘要：

  A facile deoxygenation of a systematic series of substituted 2,2-dimethyl-7-hydroxy-4-chromanones via their sulfonate, isourea, and thiocarbamate derivatives is reported. The synthesis of novel 2,2-dimethyl-7-mercapto-4-chromanones has been accomplished by the hydrolysis of the corresponding thiocarbamates. The scope and limitations of different deoxygenation procedures in the case of these hydroxybenzopyranoids are also presented.

  DOI：

  10.1021/jo00100a038
• 作为产物：
  描述：

  5,7-二羟基-2,2-二甲基-2,3-二氢-4H-苯并吡喃-4-酮 在 三乙烯二胺 、 氢氧化钾 、 N,N-二甲基苯胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-hydroxy-7-mercapto-2,2-dimethyl-4-chromanone
  参考文献：
  名称：

  Modification of Hydroxybenzopyranoids: Facile Deoxygenation of 2,2-Dimethyl-7-hydroxy-4-chromanones and a New Approach to Their Novel Mercapto Analogs

  摘要：

  A facile deoxygenation of a systematic series of substituted 2,2-dimethyl-7-hydroxy-4-chromanones via their sulfonate, isourea, and thiocarbamate derivatives is reported. The synthesis of novel 2,2-dimethyl-7-mercapto-4-chromanones has been accomplished by the hydrolysis of the corresponding thiocarbamates. The scope and limitations of different deoxygenation procedures in the case of these hydroxybenzopyranoids are also presented.

  DOI：

  10.1021/jo00100a038

文献信息

• 9-Hydroxydibenzo[b,d]pyrans and intermediates
  申请人：Pfizer Inc.

  公开号：US04143139A1

  公开（公告）日：1979-03-06

  9-Hydroxydibenzo[b,d]pyrans useful as analgesics, hypotensives, immunosuppressants, tranquilizers; as anti-secretory and anti-anxiety drugs; intermediates therefor and derivatives thereof having the formulae ##STR1## wherein R is hydrogen or alkanoyl having from one to five carbon atoms; R.sub.1 is hydrogen, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.P --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group; Each of R.sub.4 and R.sub.5 is hydrogen, methyl or ethyl; R.sub.0 is oxo or alkylenedioxy having from two to four carbon atoms; Z is (a) alkylene having from one to nine carbon atoms; (b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --wherein each of (alk.sub.1) and (alk.sub.2) has from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 9; Each of m and n is 0 or 1; X is O, S, SO or SO.sub.2 ; and W is methyl, phenyl, p-chlorophenyl, p-fluorophenyl, pyridyl, piperidyl, cycloalkyl having from 3 to 7 carbon atoms, or monosubstituted cycloalkyl wherein the substituent is phenyl, p-chlorophenyl or p-fluorophenyl; With the proviso that when W is methyl, Z is --(alk.sub.1).sub.m --X---(alk.sub.2).sub.n --.

  9-羟基二苯并[b,d]吡喃可用作镇痛剂、降压药、免疫抑制剂、镇静剂；作为抗分泌和抗焦虑药物；其中间体和具有以下式的衍生物 ##STR1## 其中R为氢或具有一至五个碳原子的烷酰基；R.sub.1为氢、具有一至五个碳原子的烷酰基或--CO--(CH.sub.2).sub.P --NR.sub.2 R.sub.3，其中p为0或1至4的整数；当单独考虑R.sub.2和R.sub.3时，R.sub.2和R.sub.3分别为氢或具有一至四个碳原子的烷基；当R.sub.2和R.sub.3与它们连接的氮一起形成与哌啶基、吡咯基、吡咯啉基、吗啉基和N-烷基哌嗪基中的一种所选的5-或6-成员杂环环；R.sub.4和R.sub.5中的每一个为氢、甲基或乙基；R.sub.0为氧代或具有二至四个碳原子的烷二氧基；Z为(a)具有一至九个碳原子的烷基；(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --其中每个(alk.sub.1)和(alk.sub.2)具有1至9个碳原子，但要求(alk.sub.1)加(alk.sub.2)中碳原子的总和不大于9；m和n中的每一个为0或1；X为O、S、SO或SO.sub.2；W为甲基、苯基、对氯苯基、对氟苯基、吡啶基、哌啶基、具有3至7个碳原子的环烷基，或单取代环烷基，其中取代基为苯基、对氯苯基或对氟苯基；但要求当W为甲基时，Z为--(alk.sub.1).sub.m --X---(alk.sub.2).sub.n --。
• Bicyclic benzo fused compounds
  申请人：Pfizer Inc.

  公开号：US04486428A1

  公开（公告）日：1984-12-04

  Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups; A' is: (1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof; (2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl; Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 where Q.sub.4 is CN or COOH or certain esters thereof; R.sub.1 is hydrogen, benzyl or certain acyl groups; R.sub.4 is hydrogen, certain alkyl or certain aralkyl groups; R.sub.5 is hydrogen or certain alkyl groups; Z is (C.sub.1 -C.sub.9)alkylene, optionally interrupted by O, S, SO or SO.sub.2 ; and W is hydrogen, methyl, certain aryl or cycloalkyl groups; useful in mammals as analgesics, tranquilizers, antiemetic agents, diuretics, anticonvulsants, antidiarrheals, antitussives, in treatment of glaucoma, and intermediates therefore.

  公式为##STR1##的双环融合苯类化合物及其药学上可接受的阳离子和酸盐，其中M为O、CH.sub.2或NR.sub.6；R.sub.6为氢、甲酰基、羟甲基苄氧基或某些羧烷氧基烷基、烷酰基、烷基、芳基烷基或芳基烷基羰基基团；A'为：(1) A，其中A和B中的一个为氢，使得当A为氢时，B为C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q且f为1或2；当B为氢时，A为C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q且f为0或1，当A和OR.sub.1一起形成内酯或其某些衍生物时；(2) A'为##STR2##(3) A'为Q.sub.3；Q为CO.sub.2 R.sub.7、COR.sub.8、C(OH)R.sub.8 R.sub.9、CN、CONR.sub.12 R.sub.13、CH.sub.2 NR.sub.12 R.sub.13、CH.sub.2 NHCOR.sub.14、CH.sub.2 NHSO.sub.2 R.sub.17或5-四唑基；Q.sub.3为##STR3##5-四唑基、CH.sub.2 CONHCOR.sub.7、COOH或其某些酯、酰胺、羧酰亚胺或磺酰亚胺衍生物，CONHOH、CONHCONH.sub.2或COCH.sub.2 Q.sub.4，其中Q.sub.4为CN或COOH或其某些酯；R.sub.1为氢、苄基或某些酰基；R.sub.4为氢、某些烷基或某些芳基烷基；R.sub.5为氢或某些烷基；Z为(C.sub.1-C.sub.9)烷基，可由O、S、SO或SO.sub.2中断；W为氢、甲基、某些芳基或环烷基；在哺乳动物中作为镇痛剂、镇静剂、止吐剂、利尿剂、抗癫痫药、止泻药、镇咳剂、治疗青光眼和其中间体。
• Seboek Peter, Timar Tibor, Eszenyi Tibor, J. Org. Chem, 59 (1994) N 21, S 6318- 6321
  作者：Seboek Peter, Timar Tibor, Eszenyi Tibor

  DOI：——

  日期：——
• US4143139A
  申请人：——

  公开号：US4143139A

  公开（公告）日：1979-03-06
• US4243674A
  申请人：——

  公开号：US4243674A

  公开（公告）日：1981-01-06