1,1-dimethyl-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline | 1258843-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1,1-dimethyl-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 7-methoxy-1,1-dimethyl-3,4-dihydro-2H-isoquinolin-6-ol
• CAS: 1258843-26-3
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: CYCNRAAIWKWNNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(2-氨基乙基)-2-甲氧基苯酚 、 丙酮 在 Ca(hfip)₂ 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到1,1-dimethyl-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Calcium-Promoted Pictet-Spengler Reactions of Ketones and Aldehydes

  摘要：

  Calcium bis-1,1,1,3,3,3-hexafluoroisopropoxide is shown to be an effective catalyst for Pictet-Spengler reactions of 3-hydroxyphenethylamine and 3-hydroxy-4-methoxyphenethylamine with various aldehydes and ketones. Previous Lewis acid catalyzed Pictet-Spengler reactions of unactivated ketones typically require two separate reactions (imine formation, cyclization) to obtain the same results. The reactions described within directly provide 1,1'-disubstituted tetrahydroisoquinolines from the corresponding amine and ketone. These rare examples of Pictet-Spengler reactions of unactivated ketones demonstrate the unique nature of calcium as a Lewis acid catalyst.

  DOI：

  10.1021/jo1019283

文献信息

• SYNTHESIS OF NATURALLY OCCURING ECTEINASCIDINS AND RELATED COMPOUNDS
  申请人：Barrasa Valentin Martinez

  公开号：US20090163507A1

  公开（公告）日：2009-06-25

  Ecteinascidin compounds with a quinone ring for ring E are active as anti-cancer agents. Related processes and compounds are provided.

  Ecteinascidin化合物具有一个醌环的E环，可作为抗癌剂活性。提供了相关的过程和化合物。
• The synthesis of naturally occuring ecteinascidins and related compounds
  申请人：Pharma Mar S.A.U.

  公开号：EP2305689A1

  公开（公告）日：2011-04-06

  The present invention provides compounds of formula: wherein Ra and Rb together with the carbon to which they are attached form a group of formula: where each X1 is independently selected from hydrogen or substituted or unsubstituted R', OR', -(C=O)R', substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted aralkyl; wherein R' is selected from the group consisting of H, OH, NO2 NH2, SH, CN, halogen, C(=O)H, C(=O)CH3, CO2H, CO2CH3, C1-C6 alkyl, alkenyl, alkynyl, aryl, aralkyl and heterocyclic; where Rd is a substituted or unsubstituted R', OR',-(C=O)R', substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl; wherein R' is selected from the group consisting of OH, NO2, NH2, SH, CN, halogen, C(=O)H, C(=O)CH3, CO2H, CO2CH3, C1-C6 alkyl, alkenyl, alkynyl, aryl, aralkyl and heterocyclic; R7 is -OCH3 and R8 is -OH or R7 and R8 together form a group -O-CH2-O-; R12a is hydrogen, acyl, alkenyl, or alkyl-O-CO-; R21 is -H, OH or CN; X is -O- or -NH-; R5 and R18 are -OX1, wherein each X1 is independently selected from hydrogen, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2C18 alkynyl, substituted or unsubstituted aryl, and -C(=O)R' wherein R' is selected from hydrogen, OH, NO2, NH2, SH, CN, halogen, C1-C6 alkyl, alkenyl, alkynyl, aryl, aralkyl, and heterocyclic.

  本发明提供了式化合物： 其中 Ra 和 Rb 与它们所连接的碳一起形成一个式基团： 其中每个 X1 独立选自氢或取代或未取代的 R'、OR'、-(C=O)R'、取代或未取代的 烷基、取代或未取代的烷氧基、取代或未取代的烯基、取代或未取代的芳基和取代或未 取代的芳烷基；其中 R'选自由 H、OH、NO2 NH2、SH、CN、卤素、C(=O)H、C(=O)CH3、CO2H、CO2CH3、C1-C6 烷基、烯基、炔基、芳基、芳烷基和杂环组成的组； 其中 Rd 是取代或未取代的 R'、OR'、-(C=O)R'、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳基、取代或未取代的芳烷基；其中 R' 选自 OH、NO2、NH2、SH、CN、卤素、C(=O)H、C(=O)CH3、CO2H、CO2CH3、C1-C6 烷基、烯基、炔基、芳基、芳烷基和杂环组成的组； R7 是-OCH3，R8 是-OH，或 R7 和 R8 共同组成一个基团-O-CH2-O-； R12a 是氢、酰基、烯基或烷基-O-CO-； R21 是-H、OH 或 CN； X 是-O-或-NH-； R5 和 R18 是-OX1，其中每个 X1 独立选自氢、取代或未取代的 C1-C18 烷基、取代或未取代的 C2-C18 烯基、取代或未取代的 C2C18 炔基、取代或未取代的芳基和-C(=O)R'，其中 R' 选自氢、OH、NO2、NH2、SH、CN、卤素、C1-C6 烷基、烯基、炔基、芳基、芳烷基和杂环。
• Synthesis of naturally occcuring ecteinascidins and related compounds
  申请人：Martinez Valentin

  公开号：US20070093658A1

  公开（公告）日：2007-04-26

  Ecteinascidin compounds with a quinone ring for ring E are active as anti-cancer agents. Related processes and compounds are provided.
• US7767659B2
  申请人：——

  公开号：US7767659B2

  公开（公告）日：2010-08-03
• US7795260B2
  申请人：——

  公开号：US7795260B2

  公开（公告）日：2010-09-14