N-[(4S,5S)-2,2-dimethyl-4-(4-methylsulfanylphenyl)-1,3-dioxan-5-yl]-2-(5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-ylmethyl)benzamide | 696659-66-2

• 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: N-[(4S,5S)-2,2-dimethyl-4-(4-methylsulfanylphenyl)-1,3-dioxan-5-yl]-2-(5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-ylmethyl)benzamide
• CAS: 696659-66-2
• 化学式: C₃₁H₃₄N₂O₅S
• 分子量: 546.687
• InChiKey: NYGWAUQHOCZFJZ-YQVYFVOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(4S,5S)-2,2-dimethyl-4-(4-methylsulfanylphenyl)-1,3-dioxan-5-yl]-2-(5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-ylmethyl)benzamide 以 甲苯 为溶剂， 反应 22.0h， 以77%的产率得到(-)-2,3-methylenedioxy-8-oxoberbine
  参考文献：
  名称：

  Asymmetric synthesis of (R)-(+)- and (S)-(−)-2,3-methylenedioxy-8-oxoberbine (gusanlung D)

  摘要：

  The reaction of 6,7-methylenedioxy-3,4-dihydroisoquinoline with laterally lithiated o-toluamides in which the amine part derived from (1S,2S)-thiomicamine or (1R,2S)-2-amino-1-phenylpropanol, affording (R)-(+)- and (S)-(-)-2,3-methylenedioxy-8-oxoberbine in 77% and 64% yield, respectively, and with enantiomeric excess >99% is described. Physical and spectral data of the synthetic product differ from those reported for the natural alkaloid, gusanhang D. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.017
• 作为产物：
  描述：

  (1S,2S)-(+)-2-氨基-1-[4-(甲硫基)苯基-1,3-丙二醇 在 氢氧化钾 、 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 8.5h， 生成 N-[(4S,5S)-2,2-dimethyl-4-(4-methylsulfanylphenyl)-1,3-dioxan-5-yl]-2-(5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-ylmethyl)benzamide
  参考文献：
  名称：

  Asymmetric synthesis of (R)-(+)- and (S)-(−)-2,3-methylenedioxy-8-oxoberbine (gusanlung D)

  摘要：

  The reaction of 6,7-methylenedioxy-3,4-dihydroisoquinoline with laterally lithiated o-toluamides in which the amine part derived from (1S,2S)-thiomicamine or (1R,2S)-2-amino-1-phenylpropanol, affording (R)-(+)- and (S)-(-)-2,3-methylenedioxy-8-oxoberbine in 77% and 64% yield, respectively, and with enantiomeric excess >99% is described. Physical and spectral data of the synthetic product differ from those reported for the natural alkaloid, gusanhang D. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.017

文献信息

• Asymmetric synthesis of (R)-(+)- and (S)-(−)-2,3-methylenedioxy-8-oxoberbine (gusanlung D)
  作者：Maria Chrzanowska、Agnieszka Dreas、Maria D. Rozwadowska

  DOI：10.1016/j.tetasy.2004.02.017

  日期：2004.4

  The reaction of 6,7-methylenedioxy-3,4-dihydroisoquinoline with laterally lithiated o-toluamides in which the amine part derived from (1S,2S)-thiomicamine or (1R,2S)-2-amino-1-phenylpropanol, affording (R)-(+)- and (S)-(-)-2,3-methylenedioxy-8-oxoberbine in 77% and 64% yield, respectively, and with enantiomeric excess >99% is described. Physical and spectral data of the synthetic product differ from those reported for the natural alkaloid, gusanhang D. (C) 2004 Elsevier Ltd. All rights reserved.