(S)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline | 22324-82-9

• 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: (S)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (S)-(+)-cryptostyline II；(S)-cryptostyline II；(+)-Crytostyline II；Cryptostylin II；Cryptostylin；(1S)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
• CAS: 22324-82-9
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: KYWZIVDVIANHDJ-FQEVSTJZSA-N

物化性质

• 沸点：
  439.9±45.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸甲酯 在 palladium on activated charcoal 氢氧化钾 、 lithium aluminium tetrahydride 、 甲酸 、 PPA 、 氢气 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 36.0h， 生成 (S)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  A Novel Route to Chiral, Nonracemic 1-Alkyl- and 1-Aryl-Substituted Tetrahydroisoquinolines. Synthesis of (-)-Salsolidine and (+)-Cryptostyline II

  摘要：

  DOI：

  10.1021/jo00127a006

文献信息

• An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to N-Sulfonylarylaldimines
  作者：Kazunori Kurihara、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1002/adsc.200800631

  日期：2009.1

  A chiral N-linked C2-symmetric bidentate phosphoramidite (N-Me-BIPAM) was newly developed for the rhodium-catalyzed enantioselective addition of arylboronic acids to N-sulfonylimines. This ligand achieved high enantioselectivities in a range of 84–99% ee in additions of arylboronic acids to N-tosyl- and N-nosylarylaldimines.

  手性N-连接的C 2-对称的二齿亚磷酰胺（N -Me-BIPAM）是新开发的，用于铑催化的对N-磺酰亚胺基的芳基硼酸的对映选择性加成。除了在N-甲苯磺酰基和N-壬基芳基醛亚胺中添加芳基硼酸外，该配体还实现了84-99％ee范围内的高对映选择性。
• An efficient method for construction of tetrahydroisoquinoline skeleton via double cyclization process using ortho-vinylbenzaldehydes and amino alcohols: application to the synthesis of (S)-cryptostyline II
  作者：Kazuteru Umetsu、Naoki Asao

  DOI：10.1016/j.tetlet.2008.02.152

  日期：2008.4

  Thermal double cyclization reaction using ortho-vinylbenzaldehyde and 3-aminopropanols proceeded smoothly to give isoquinoline derivatives via 6π-azaelectrocyclization pathway. The method was applied to the efficient synthesis of (S)-cryptostyline II.

  使用邻-乙烯基苯甲醛和3-氨基丙醇进行的热双环化反应顺利进行，通过6π-氮杂电环化途径生成异喹啉衍生物。该方法被用于（S）-隐藻糖苷Ⅱ的有效合成。
• Highly Enantioselective Arylation of <i>N</i>,<i>N</i>-Dimethylsulfamoyl-Protected Aldimines Using Simple Sulfur–Olefin Ligands: Access to Solifenacin and (<i>S</i>)-(+)-Cryptostyline II
  作者：Tao Jiang、Wen-Wen Chen、Ming-Hua Xu

  DOI：10.1021/acs.orglett.7b00776

  日期：2017.4.21

  With the use of a simple sulfur–olefin ligand, a highly enantioselective rhodium-catalyzed addition of arylboroxines to N,N-dimethylsulfamoyl-protected aldimines has been achieved, allowing access to a broad range of chiral diarylmethylamines in high yields (up to 98%) with uniformly excellent enantioselectivities (up to 99% ee). This catalyst system is also applicable to the arylation of N-tosyl arylimines

  通过使用简单的硫-烯烃配体，已经实现了对映体选择性铑催化的芳基硼氧烷到N，N-二甲基氨磺酰基保护的醛亚胺的加成反应，从而可以高收率获得各种手性二芳基甲胺（高达98％ ）具有一致优异的对映选择性（高达99％ee）。该催化剂体系也适用于N-甲苯磺酰基芳胺的芳基化。通过利用这种方法，可以容易地构建一些具有手性1-芳基-1,2,3,4-四氢异喹啉核心的生物活性分子，例如Solifenacin和（S）-（+）-隐香碱II。
• Cobalt-Catalyzed Enantioselective C–H Annulation of Benzylamines with Alkynes: Application to the Modular and Asymmetric Syntheses of Bioactive Molecules
  作者：Yong-Jie Wu、Jia-Hao Chen、Ming-Ya Teng、Xiang Li、Tian-Yu Jiang、Fan-Rui Huang、Qi-Jun Yao、Bing-Feng Shi

  DOI：10.1021/jacs.3c10714

  日期：——

  enantioselective C–H functionalization strategy has revolutionized the logic of natural product synthesis. However, previous applications have heavily relied on the use of noble metal catalysts such as rhodium and palladium. Herein, we report the efficient synthesis of C1-chiral 1,2-dihydroisoquinolines (DHIQs) via enantioselective C–H/N–H annulation of picolinamides with alkynes catalyzed by a more sustainable and

  过渡金属催化的对映选择性C-H官能化策略彻底改变了天然产物合成的逻辑。然而，以前的应用严重依赖于贵金属催化剂的使用，例如铑和钯。在此，我们报道了在更可持续且更便宜的3d金属催化剂乙酸钴(II)的催化下，通过吡啶甲酰胺与炔烃的对映选择性C-H/N-H环化，有效合成了C 1 -手性1,2-二氢异喹啉(DHIQ)四水合物。以良好的收率和优异的对映选择性（高达 98% 收率和 >99% ee）获得了各种对映体富集的 DHIQ。该方法的稳健性和合成潜力通过几种四氢异喹啉生物碱的模块化和不对称合成得到了证明，这些生物碱包括( S )-降劳丹苷、( S )-劳丹苷、( S )-木洛匹宁、( S )-sebiferine和( S ) -cryptostyline II，以及 (+)-solifenacin、FR115427 和 (+)-NPS R-568 关键中间体的不对称合成。
• Substituted isoquinolines as ultra short acting neuromuscular blockers
  申请人：Avera Pharmaceuticals, Inc.

  公开号：EP1526130A1

  公开（公告）日：2005-04-27

  Ultra short acting neuromuscular blocking agents of Formula (I) which are useful as skeletal muscle relaxants during emergency intubation procedures, routine surgery and post-operative settings are disclosed, wherein q and t are independently from 0 to 4; and X1 and X2 are independently halogen; ha and hb are independently from 0 to 2; Z1 and Z2 are independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl with the proviso that Z1 and Z are not both hydrogen; Y1, Y2, Y3 and Y4 are independently hydrogen, halogen or C1-C3 alkoxy; m and p are independently 1 to 6; n and r are independently 0 to 4; with the proviso that if ha and hb are both 0, then r is 0 and n is 0 to 2; R1 and R14 are independently hydrogen, halogen, C1-C3 alkoxy, or R2 and R3 together with the carbon atoms to which they are bonded, R5 and R6 together with the carbon atoms to which they are bonded, may independently form a methylenedioxy or ethylenedioxy moiety contained in a five- or six-membered ring; W1 and W2 are carbon; and A is a pharmaceutically acceptable anion.

  本发明公开了式（I）的超短效神经肌肉阻断剂，可在紧急插管过程、常规手术和术后环境中用作骨骼肌松弛剂、 其中 q 和 t 独立地为 0 至 4；X1 和 X2 独立地为卤素；ha 和 hb 独立地为 0 至 2；Z1 和 Z2 独立地为氢、C1-C6 烷基、C2-C6 烯基或 C2-C6 烷炔基，但 Z1 和 Z 不能都是氢；Y1、Y2、Y3 和 Y4 独立地为氢、卤素或 C1-C3 烷氧基；m 和 p 独立地为 1 至 6；n 和 r 独立地为 0 至 4；R1 和 R14 独立地为氢、卤素、C1-C3 烷氧基，或 R2 和 R3 与其键合的碳原子、R5 和 R6 与其键合的碳原子可独立地形成包含在五元或六元环中的亚甲二氧基或亚乙二氧基分子；W1 和 W2 为碳；以及 A 为药学上可接受的阴离子。