(+/-)-N¹-noresermethole | 46479-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+/-)-N¹-noresermethole
• 英文别名: (+/-)-5-O-methyl-1-noreseroline；5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole；1,2,3,3a,8,8a-hexahydro-5-methoxy-3a,8-dimethylpyrrolo[2,3-b]indole；(+/-)-1,2,3,3a,8,8a-Hexahydro-5-methoxy-3a,8-dimethyl-pyrrolo<2,3-b>indol；dl-N(b)-Noresermethol；1,2,3,3A,8,8A-Hexahydro-5-methoxy-3A,8-dimethyl-pyrrolo[2,3-B]indole；7-methoxy-4,8b-dimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indole
• CAS: 46479-70-3
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: JLWSGVHTOXXQAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-N¹-noresermethole 在 sodium pentyl oxide 作用下， 以 戊醇 、 氯仿 为溶剂， 反应 1.0h， 生成 (+)-(10R)-5-O-methyl-1-noreseroline
  参考文献：
  名称：

  通过（甲基苄基）脲类似物的热分解制备旋光性仲胺：（+）-和（-）-美甲胺的绝对构型。初步沟通† ‡

  摘要：

  （±）-美甲胺（（±）-1）的（α-甲基苄基）脲非对映异构体4和5和（±）-1-去甲甾氨酸O-甲基醚（（±）-3）的6和7的热解。回流的醇除了可以循环利用的（α-甲基苄基）胺的光学纯氨基甲酸酯外，还以高收率提供了光学纯的胺。通过X射线衍射分析来确定（-）-甲酰胺胺盐酸盐（（-）- 1 ·HCl）的绝对构型。

  DOI：

  10.1002/hlca.19860690205
• 作为产物：
  描述：

  (5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile 在 红铝 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (+/-)-N¹-noresermethole
  参考文献：
  名称：

  Reduction of Oxidoles with Sodium Bis(2-methoxyethoxy)aluminium Hydride, a Novel Reducing Agent

  摘要：

  1,3-Dimethyl-3-(2'-dimethylaminoethyl)-5-tetrahydropyranyloxyoxindole (5), obtained on C3-alkylation of oxindole (4), was reduced stereoselectively with sodium bis(2-methoxyethoxy)alum in um hydride (Vitride) to carbinolamine (6). Oxindoles (7, 8, 9, 10 and 11) similarly were reduced and cyclized to (+/-)-N-1-noresermethole (13), (+/-)-O-tetrahydropyranyl-N-1-noreseroline (14), (+/-)-physovenol methyl ether (15), (+/-)-esermethole (16), and (+/-)-N-1-benzylnoresermethole (17), respectively.

  DOI：

  10.3987/com-94-s(b)39

文献信息

• Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and)
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US04791107A1

  公开（公告）日：1988-12-13

  There are described compounds of the formula ##STR1## where (a) X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  描述了以下化合物的化学式##STR1## 其中（a）X为O或S；（b）R为H、loweralkyl、##STR2## 其中Y为O或S；R.sub.2为烷基、环烷基、双环烷基、环烯基、芳基、芳基loweralkyl、杂环芳基或杂环芳基loweralkyl，R.sub.3为H或烷基，或整体视为--NR.sub.2 R.sub.3时为1-吡咯基、1-哌啶基、4-吗啉基、4-硫代吗啉基、1-哌嗪基、4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚胺基)-1-咪唑烷基）和R.sub.4为氢、loweralkyl、芳基loweralkyl、二芳基loweralkyl、芳基或杂环芳基，（c）m为1或2；（d）每个Z独立地为H、loweralkyl、卤素、硝基、--NH.sub.2、loweralkylcarbonylamino、arylcarbonylamino、loweralkoxycarbonylamino或loweralkylamino，（e）R.sub.1为H、loweralkyl、芳基loweralkyl、杂环芳基loweralkyl、环烷基甲基或loweralkenylmethyl，但当X为O时，m为1、Z为H且R.sub.1为甲基时，R不是--CONHCH.sub.3、--CONHC.sub.6 H.sub.5、氢、甲基或乙基，当X为O时，m为1且Z和R.sub.1均为氢时，R不是氢或甲基，以及其药用可接受的酸盐，可用作增强记忆和镇痛剂。
• Fragmentation of Optically Active (1-Phenylethyl)- and (1-Naphthylethyl)ureas in Refluxing Alcohols: Easy Preparation of Optically Active Amines of High Optical Purity
  作者：Bernhard Schönenberger、Arnold Brossi

  DOI：10.1002/hlca.19860690620

  日期：1986.9.10

  (1-Phenylethyl)- and (1-naphthylethyl)ureas, obtained in the reaction of racemic amines with optically pure isocyanates, are separated and then decomposed in refluxing alcohols, to afford optically pure secondary amines and optically pure alkyl carbamates in quantitative yields. The scope of this fragmentation for the resolution of racemic mixtures of amines is illustrated by several examples of biologically

  将在外消旋胺与旋光纯的异氰酸酯反应中获得的（1-苯乙基）-和（1-萘基乙基）脲分离，然后在回流的醇中分解，以定量收率得到旋光纯的仲胺和旋光的氨基甲酸烷基酯。用于拆分胺的外消旋混合物的这种裂解作用的范围由生物学上重要的化合物的几个例子说明。通过这种裂解获得的氨基甲酸酯可以容易地再循环。
• Method for preparing 1, 2, 3, 3A, 8, 8A-hexahydro-3A, 8 (and 1, 3A,
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US05621114A1

  公开（公告）日：1997-04-15

  There are described compounds of the formula ##STR1## where (a) X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  描述了一种化合物的公式 ##STR1## 其中：(a) X为O或S; (b) R为H、低烷基、##STR2## 其中Y为O或S; R.sub.2为烷基、环烷基、双环烷基、环烯基、芳基、芳基低烷基、杂环芳基或杂环芳基低烷基，R.sub.3为H或烷基，或作为整体的--NR.sub.2R.sub.3为1-吡咯基、1-哌啶基、4-吗啉基、4-硫代吗啉基、1-哌嗪基、4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚氨基)-1-咪唑啉基)，R.sub.4为氢、低烷基、芳基低烷基、二芳基低烷基、芳基或杂环芳基，(c) m为1或2；(d) 每个Z独立地为H、低烷基、卤素、硝基、--NH.sub.2、低烷基羰基氨基、芳基羰基氨基、低烷氧羰基氨基或低烷基氨基；(e) R.sub.1为H、低烷基、芳基低烷基、杂环芳基低烷基、环烷基甲基或低烯基甲基，但当X为O、m为1、Z为H且R.sub.1为甲基时，R不为--CONHCH.sub.3、--CONHC.sub.6H.sub.5、氢、甲基或乙基；当X为O、m为1且Z和R.sub.1都为氢时，R不为氢或甲基。它们的药物可接受的酸盐可用作记忆增强和镇痛剂。
• Memory enhancing and analgesic 1,2,3,3a,8,8a,-hexahydro-3a,8(and
  申请人：Hoechst-Marion-Roussel, Inc.

  公开号：US05639892A1

  公开（公告）日：1997-06-17

  There are described compounds of the formula ##STR1## where X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicyclcalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2.sub.R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heheroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is l, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is l and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and, pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  描述了一种化合物的公式 ##STR1## 其中X为O或S; (b) R为H，低碳基，##STR2## 其中Y为O或S; R.sub.2为烷基，环烷基，双环烷基，环烯基，芳基，芳基低碳基，杂环芳基或杂环芳基低碳基，R.sub.3为H或烷基，或整个--NR.sub.2.sub.R.sub.3基团为1-吡咯烷基，1-哌啶基，4-吗啉基，4-硫代吗啉基，1-哌嗪基，4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚胺)-1-咪唑烷基)，R.sub.4为氢，低碳基，芳基低碳基，二芳基低碳基，芳基或杂环芳基，(c) m为1或2; (d) 每个Z独立地为H，低碳基，卤素，硝基，--NH.sub.2，低碳基羰基氨基，芳基羰基氨基，低碳基氧羰基氨基或低碳基氨基，和 (e) R.sub.1为H，低碳基，芳基低碳基，杂环芳基低碳基，环烷基甲基或低碳烯基甲基，但须注意当X为O时，m为1，Z为H且R.sub.1为甲基时，R不是--CONHCH.sub.3，--CONHC.sub.6 H.sub.5，氢，甲基或乙基，当X为O，m为1且Z和R.sub.1都为氢时，R不是氢或甲基，以及其药学上可接受的酸盐，其可用作增强记忆和镇痛剂。
• Method of preparing 1,2,3,3a,8,8a-hexahydro-3a,8(and 1,3a,8)-Di(and
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US05541340A1

  公开（公告）日：1996-07-30

  There are described compounds of the formula ##STR1## where (a) X is O or S; (b) R is H, loweralkyl, ##STR2## where Y is O or S; R.sub.2 is alkyl, cycloalkyl, bicycloalkyl, cycloalkenyl, aryl, arylloweralkyl, heteroaryl or heteroarylloweralkyl, R.sub.3 is H or alkyl, or the group --NR.sub.2 R.sub.3 taken as a whole is 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 4-thiomorpholinyl, 1-piperazinyl, 4-methyl-1-piperazinyl or 2-(2,6-dichlorophenylimino)-1-imidazolidinyl) and R.sub.4 is hydrogen, loweralkyl, arylloweralkyl, diarylloweralkyl, aryl or heteroaryl, (c) m is 1 or 2; (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino, and (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, with the proviso that when X is O, m is 1, Z is H and R.sub.1 is methyl, R is not --CONHCH.sub.3, --CONHC.sub.6 H.sub.5, hydrogen, methyl or ethyl, and that when X is O, m is 1 and Z and R.sub.1 are both hydrogen, R is not hydrogen or methyl, and pharmaceutically acceptable acid addition salts thereof which are useful as memory-enhancing and analgesic agents.

  该文描述了式子##STR1##的化合物，其中(a)X为O或S；(b)R为H、loweralkyl、##STR2##其中Y为O或S；R.sub.2为alkyl、cycloalkyl、bicycloalkyl、cycloalkenyl、aryl、arylloweralkyl、heteroaryl或heteroarylloweralkyl，R.sub.3为H或alkyl，或者--NR.sub.2 R.sub.3整体为1-吡咯烷基、1-哌啶基、4-吗啉基、4-硫代吗啉基、1-哌嗪基、4-甲基-1-哌嗪基或2-(2,6-二氯苯基亚胺)-1-咪唑啉基，R.sub.4为氢、loweralkyl、arylloweralkyl、diarylloweralkyl、aryl或heteroaryl，(c)m为1或2；(d)每个Z独立地为H、loweralkyl、卤素、硝基、--NH.sub.2、loweralkylcarbonylamino、arylcarbonylamino、loweralkoxycarbonylamino或loweralkylamino；(e)R.sub.1为H、loweralkyl、arylloweralkyl、heteroarylloweralkyl、cycloalkylmethyl或loweralkenylmethyl，但当X为O、m为1、Z为H且R.sub.1为甲基时，R不为--CONHCH.sub.3、--CONHC.sub.6 H.sub.5、氢、甲基或乙基，当X为O、m为1且Z和R.sub.1均为氢时，R不为氢或甲基，以及其药学上可接受的酸加成盐，其作为增强记忆和镇痛剂。