(3S)-(+)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone | 868157-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (3S)-(+)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone
• CAS: 868157-83-9
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: LTGANBFRQIBGLJ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S)-(+)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone 在 lithium aluminium tetrahydride 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
• 作为产物：
  描述：

  ((S)-4-Benzyl-2,2-dimethyl-oxazolidin-3-yl)-{2-[2-(2,2-dimethoxy-ethylamino)-2-(3,4-dimethoxy-phenyl)-ethyl]-phenyl}-methanone 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (3R)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone 、 (3S)-(+)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone
  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.