(R)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline | 156545-91-4

• 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: (R)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (R)-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid methyl ester；Methyl 2-[(1R)-1,2,3,4-tetrahydroisoquinolin-1-yl]acetate
• CAS: 156545-91-4
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: ZYKBDGYQTKXXTM-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 (R)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline 反应 6.0h， 以73%的产率得到(R)-2-(2-methoxycarbonylethyl)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Alkoxycarbonylmethylation of (3R,10bS)-3-Phenyl-2,3,5,6-tetrahydro-10bH-oxazolo(2,3-a)isoquinoline.

  摘要：

  作为手性 1-烷基四氢异喹啉合成系列研究的一部分，我们研究了 1-烷氧羰基甲基-1，2，3，4-四氢异喹啉（IV）的不对称合成。尝试了从 (3R，10bS)-3-苯基-2，3，5，6-四氢-10bH-恶唑并[2，3-a]异喹啉（1）出发，利用分子间和分子内 Reformatsky 型反应的两种合成方法，但无法获得较高的立体选择性。为了确定通过 Reformatsky 型反应得到的化合物 (2, 3) 的绝对结构，研究人员将 3a 转化为手性 1, 3, 4, 6, 7, 11b-hexahydro-2H-benzo[a]quinolizine (14)。

  DOI：

  10.1248/cpb.42.796
• 作为产物：
  描述：

  methyl (R)-2-(1,2,3,4-tetrahydroisoquinolin-1-yl)acetate hydrochloride 在 potassium carbonate 作用下， 以 水 为溶剂， 以138 mg的产率得到(R)-1-methoxycarbonylmethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-acetic acid esters

  摘要：

  The enantiomers of 1,2,3,4-tetrahydroisoquinoline- and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-acetic acids were prepared via Burkholderia cepacia lipase (lipase PS-D)-catalyzed kinetic resolution of the corresponding ethyl and 2-methoxyethyl esters using enantioselective (E>200) hydrolysis in DIPE. The (S)-acids were produced enzymatically, whereas the (R)-acids were obtained via the chemical hydrolysis of the unreacted (R)-esters. The solvent and its water content had major effects on both reactivity and enantioselectivity. The methoxyethyl moiety of the ester had a key role concerning the reactivity of the substrates. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.032

文献信息

• Photoredox activation and anion binding catalysis in the dual catalytic enantioselective synthesis of β-amino esters
  作者：Giulia Bergonzini、Corinna S. Schindler、Carl-Johan Wallentin、Eric N. Jacobsen、Corey R. J. Stephenson

  DOI：10.1039/c3sc52265b

  日期：——

  The enantioselective oxidative C–H functionalization of tetrahydroisoquinoline derivatives is achieved through the merger of photoredox and asymmetric anion-binding catalysis. This combination of two distinct catalysis concepts introduces a potentially general approach to asymmetric transformations in oxidative photocatalysis.

  通过光氧化还原和不对称阴离子结合催化的结合，实现了四氢异喹啉衍生物的对映选择性氧化-H官能化。 两种不同催化概念的结合为氧化光催化中的不对称转化引入了一种潜在的一般方法。
• Enantioselective Thiourea-Catalyzed Acyl-Mannich Reactions of Isoquinolines
  作者：Mark S. Taylor、Norihito Tokunaga、Eric N. Jacobsen

  DOI：10.1002/anie.200502277

  日期：2005.10.21
• Lipase-catalyzed kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-acetic acid esters
  作者：Tihamér A. Paál、Enikő Forró、Ferenc Fülöp、Arto Liljeblad、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2008.11.032

  日期：2008.12

  The enantiomers of 1,2,3,4-tetrahydroisoquinoline- and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-acetic acids were prepared via Burkholderia cepacia lipase (lipase PS-D)-catalyzed kinetic resolution of the corresponding ethyl and 2-methoxyethyl esters using enantioselective (E>200) hydrolysis in DIPE. The (S)-acids were produced enzymatically, whereas the (R)-acids were obtained via the chemical hydrolysis of the unreacted (R)-esters. The solvent and its water content had major effects on both reactivity and enantioselectivity. The methoxyethyl moiety of the ester had a key role concerning the reactivity of the substrates. (C) 2008 Elsevier Ltd. All rights reserved.
• Alkoxycarbonylmethylation of (3R,10bS)-3-Phenyl-2,3,5,6-tetrahydro-10bH-oxazolo(2,3-a)isoquinoline.
  作者：Yasuo TAKEUCHI、Yoshio KAMADA、Koji NISHIMURA、Hiromi NISHIOKA、Masayo NISHIKAWA、Kuniko HASHIGAKI、Masatoshi YAMATO、Takashi HARAYAMA

  DOI：10.1248/cpb.42.796

  日期：——

  As part of a series of studies on synthesis of chiral 1-alkyltetrahydroisoquinolines, asymmetric synthesis of 1-alkoxycarbonylmethyl-1, 2, 3, 4-tetrahydroisoquinolie (IV) was investigated. Two synthetic approaches using intermolecular and intramolecular Reformatsky-type reactions from (3R, 10bS)-3-phenyl-2, 3, 5, 6-tetrahydro-10bH-oxazolo[2, 3-a]isoquinoline (1) were attempted, but high stereoselectivity could not be obtained. For the purpose of determining the absolute structures of the compounds (2, 3) obtained by the Reformatsky-type reactions, transformation of 3a to a chiral 1, 3, 4, 6, 7, 11b-hexahydro-2H-benzo[a]quinolizine (14) was investigated.

  作为手性 1-烷基四氢异喹啉合成系列研究的一部分，我们研究了 1-烷氧羰基甲基-1，2，3，4-四氢异喹啉（IV）的不对称合成。尝试了从 (3R，10bS)-3-苯基-2，3，5，6-四氢-10bH-恶唑并[2，3-a]异喹啉（1）出发，利用分子间和分子内 Reformatsky 型反应的两种合成方法，但无法获得较高的立体选择性。为了确定通过 Reformatsky 型反应得到的化合物 (2, 3) 的绝对结构，研究人员将 3a 转化为手性 1, 3, 4, 6, 7, 11b-hexahydro-2H-benzo[a]quinolizine (14)。