1-<4-(2,3-Dimethoxyphenyl)-1,2,3,4-tetrahydro-1-methyl-pyrid-4-yl>-4-hydroxy-1-butanone | 87766-67-4

• 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: 1-<4-(2,3-Dimethoxyphenyl)-1,2,3,4-tetrahydro-1-methyl-pyrid-4-yl>-4-hydroxy-1-butanone
• 英文别名: 1-[4-(2,3-Dimethoxyphenyl)-1,2,3,4-tetrahydro-1-methylpyrid-4-yl]-4-hydroxy-1-butanone；1-[4-(2,3-dimethoxyphenyl)-1-methyl-2,3-dihydropyridin-4-yl]-4-hydroxybutan-1-one
• CAS: 87766-67-4
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: ZZJSECMJLDXPGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<4-(2,3-Dimethoxyphenyl)-1,2,3,4-tetrahydro-1-methyl-pyrid-4-yl>-4-hydroxy-1-butanone 生成 3-[(1R,5S,6R)-5-(2,3-dimethoxyphenyl)-2-methyl-7-oxa-2-azabicyclo[3.2.1]octan-6-yl]propan-1-ol
  参考文献：
  名称：

  CIGANEK, E.;SHENVI, B. ASHOKKUMAR

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(2,3-Dihydro-5-furyl)-4-(2,3-dimethoxyphenyl)-1-methyl-1,2,3,4-tetrahydropyridine 在 盐酸 作用下， 反应 0.25h， 生成 1-<4-(2,3-Dimethoxyphenyl)-1,2,3,4-tetrahydro-1-methyl-pyrid-4-yl>-4-hydroxy-1-butanone
  参考文献：
  名称：

  Convenient synthesis of 3-methyl-2,3,4,4a.alpha.,5,6,7,7a.alpha.-octahydro-1H-benzofuro[3,2-e]isoquinoline

  摘要：

  DOI：

  10.1021/jo00190a019

文献信息

• Certain tetrahydropyridine intermediates
  申请人：E. I. Du Pont de Nemours & Co.

  公开号：US04415736A1

  公开（公告）日：1983-11-15

  Process for preparing analgesic and narcotic antagonistic isoquinolines comprising: (a) contacting and reacting a lithiated anisole or alkyl phenyl ether, optionally substituted at the 3-position to the lithium atom, with a 4-piperidone to yield a 4-aryl-4-piperidinol; (b) dehydrating the piperidinol to a 4-aryl-1,2,3,6-tetrahydropyridine; (c) metalating and acylating the 1,2,3,6-tetrahydropyridine to yield a 1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-4-hydroxy-1-butanone; (d) reducing the ketone moiety of the butanone to yield a 5-aryl-7-oxa-2-azabicyclo[3.2.1]-octane-6-propanol; (e) converting the alcohol moiety of the propanol to L to yield a 5-aryl-6-[3-(L)propyl]-7-oxa-2-azabicyclo[3.2.1]octane in which L is a leaving group selected from the group consisting of -Cl, -Br, -I, p-MeC.sub.6 H.sub.4 SO.sub.3 - and MeSO.sub.3 -. (f) opening the amino furan ring of the bicyclooctane to yield a 4-(L)-1-(4-aryl-1,2,3,4-tetrahydropyrid-4-yl)-1-butanol derivative; (g) closing the 6-carbon ring of the butanol derivative by intramolecular reaction of the enamine and leaving group to yield a 4a-aryl-2,3,4,4a,5,6,7,8-octahydro-5-isoquinolinol or derivative thereof; and (h) reducing the enamine double bond of the octahydro-5-isoquinolinol or derivative thereof to yield a 4a-aryldecahydro-5-isoquinolinol or derivative thereof and (i) cyclizing the decahydro-5-isoquinolinol or derivative to yield a 2,3,4,4a,5,6,7,7a-octahydro-1H-benzofuro-[3,2-e]isoquinoline, or, (h) cyclizing the octahydro-5-isoquinolinol or derivative thereof to yield a 2,3,5,6,7,7a-hexahydro-1H-benzofuro-[3,2-e]isoquinoline and (i) reducing the enamine double bond of the isoquinoline.

  制备镇痛药和麻醉拮抗剂异喹啉的过程包括：（a）将锂化的苯甲醚或烷基苯基醚（可选择在3位替换为锂原子）与4-哌啶酮接触反应，生成4-芳基-4-哌啶醇；（b）脱水哌啶醇成为4-芳基-1,2,3,6-四氢吡啶；（c）金属化和酰化1,2,3,6-四氢吡啶，生成1-(4-芳基-1,2,3,4-四氢吡啶-4-基)-4-羟基-1-丁酮；（d）还原丁酮的酮基，生成5-芳基-7-氧杂-2-氮杂双环[3.2.1]-辛烷-6-丙醇；（e）转化丙醇的醇基，得到5-芳基-6-[3-(L)丙基]-7-氧杂-2-氮杂双环[3.2.1]辛烷，其中L是从群组中选择的离去基，所述群组包括-Cl，-Br，-I，p-MeC.sub.6H.sub.4SO.sub.3-和MeSO.sub.3-。（f）打开双环辛烷的氨基呋喃环，得到4-(L)-1-(4-芳基-1,2,3,4-四氢吡啶-4-基)-1-丁醇衍生物；（g）通过恩酰亚胺和离去基的分子内反应关闭丁醇衍生物的6碳环，得到4a-芳基-2,3,4,4a,5,6,7,8-八氢-5-异喹啉醇或其衍生物；（h）还原八氢-5-异喹啉醇或其衍生物的恩酰亚胺双键，得到4a-芳基-十氢-5-异喹啉醇或其衍生物；（i）环化十氢-5-异喹啉醇或其衍生物，生成2,3,4,4a,5,6,7,7a-八氢-1H-苯并呋喃[3,2-e]异喹啉，或者（h）环化八氢-5-异喹啉醇或其衍生物，生成2,3,5,6,7,7a-六氢-1H-苯并呋喃[3,2-e]异喹啉，（i）还原异喹啉的恩酰亚胺双键。
• CIGANEK, E.;SHENVI, B. ASHOKKUMAR
  作者：CIGANEK, E.、SHENVI, B. ASHOKKUMAR

  DOI：——

  日期：——
• SHENVI, ASHOKKUMAR, B.
  作者：SHENVI, ASHOKKUMAR, B.

  DOI：——

  日期：——
• SHENVI, ASHOK, B.;CIGANEK, E., J. ORG. CHEM., 1984, 49, N 16, 2942-2947
  作者：SHENVI, ASHOK, B.、CIGANEK, E.

  DOI：——

  日期：——
• SHENVI, ASHOKKUMAR B.
  作者：SHENVI, ASHOKKUMAR B.

  DOI：——

  日期：——