(S)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline | 868157-85-1

• 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)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 868157-85-1
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: JFEUAOJYSYBNJE-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 在 盐酸 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-(-)-2,2-dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine
  参考文献：
  名称：

  Synthesis of (S)-(−)- and (R)-(+)-O-methylbharatamine using a diastereoselective Pomeranz–Fritsch–Bobbitt methodology

  摘要：

  Laterally lithiated (S)-(-)- and (R)-(+)-o-toluamides 6 with a chiral auxiliary derived from (S)- and (R)-phenylalaninol, respectively, were used as the building blocks and chirality inductors in the asymmetric modification of the Pomeranz-Fritsch-Bobbitt synthesis of isoquinoline alkaloids. Their addition to imine 2 proceeded with partial cyclization, giving isoquinolones (+)-7 and (-)-7 along with acyclic products, (-)-8 and (+)-8, respectively. LAH-reduction of (+)-7 and (-)-7, followed by cyclization, afforded both enantiomers of the alkaloid, (S)-(-)- and (R)-(+)-O-methylbharatamine 5, in 32% and 40% overall yield and with 88% and 73% ees, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.025
• 作为产物：
  描述：

  (4S)-2,2-dimethyl-3-o-toluoyl-4-benzyloxazolidine 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis of (S)-(−)- and (R)-(+)-O-methylbharatamine using a diastereoselective Pomeranz–Fritsch–Bobbitt methodology

  摘要：

  Laterally lithiated (S)-(-)- and (R)-(+)-o-toluamides 6 with a chiral auxiliary derived from (S)- and (R)-phenylalaninol, respectively, were used as the building blocks and chirality inductors in the asymmetric modification of the Pomeranz-Fritsch-Bobbitt synthesis of isoquinoline alkaloids. Their addition to imine 2 proceeded with partial cyclization, giving isoquinolones (+)-7 and (-)-7 along with acyclic products, (-)-8 and (+)-8, respectively. LAH-reduction of (+)-7 and (-)-7, followed by cyclization, afforded both enantiomers of the alkaloid, (S)-(-)- and (R)-(+)-O-methylbharatamine 5, in 32% and 40% overall yield and with 88% and 73% ees, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.025

文献信息

• Synthesis of (S)-(−)- and (R)-(+)-O-methylbharatamine using a diastereoselective Pomeranz–Fritsch–Bobbitt methodology
  作者：Maria Chrzanowska、Agnieszka Dreas、Maria D. Rozwadowska

  DOI：10.1016/j.tetasy.2005.07.025

  日期：2005.9

  Laterally lithiated (S)-(-)- and (R)-(+)-o-toluamides 6 with a chiral auxiliary derived from (S)- and (R)-phenylalaninol, respectively, were used as the building blocks and chirality inductors in the asymmetric modification of the Pomeranz-Fritsch-Bobbitt synthesis of isoquinoline alkaloids. Their addition to imine 2 proceeded with partial cyclization, giving isoquinolones (+)-7 and (-)-7 along with acyclic products, (-)-8 and (+)-8, respectively. LAH-reduction of (+)-7 and (-)-7, followed by cyclization, afforded both enantiomers of the alkaloid, (S)-(-)- and (R)-(+)-O-methylbharatamine 5, in 32% and 40% overall yield and with 88% and 73% ees, respectively. (c) 2005 Elsevier Ltd. All rights reserved.