(1R)-5,7,8-trimethoxy-6-methyl-1-(phenylmethoxymethyl)-1,2,3,4-tetrahydroisoquinolin-4-ol | 271578-85-9

• 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: (1R)-5,7,8-trimethoxy-6-methyl-1-(phenylmethoxymethyl)-1,2,3,4-tetrahydroisoquinolin-4-ol
• CAS: 271578-85-9
• 化学式: C₂₁H₂₇NO₅
• 分子量: 373.449
• InChiKey: ANTOFJIKUZYBSG-VYRBHSGPSA-N

物化性质

• 沸点：
  514.4±50.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R)-5,7,8-trimethoxy-6-methyl-1-(phenylmethoxymethyl)-1,2,3,4-tetrahydroisoquinolin-4-ol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 戴斯-马丁氧化剂 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 tert-butyl N-[(2S)-3-(2-formyl-3,4,6-trimethoxy-5-methylphenyl)-1-oxo-1-[(1R)-5,7,8-trimethoxy-6-methyl-4-oxo-1-(phenylmethoxymethyl)-1,3-dihydroisoquinolin-2-yl]propan-2-yl]-N-methylcarbamate
  参考文献：
  名称：

  A novel face specific Mannich closure providing access to the saframycin-ecteinascidin series of piperazine based alkaloids

  摘要：

  The Mannich-like closure of 10-->6 directly provides the backbone stereochemistry required for the titled alkaloids, in contrast to the stereochemical outcome in a related earlier case (3-->4). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00106-4
• 作为产物：
  描述：

  3,5-dimethoxy-2-hydroxy-4-methyl benzyl alcohol 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 95.0h， 生成 (1R)-5,7,8-trimethoxy-6-methyl-1-(phenylmethoxymethyl)-1,2,3,4-tetrahydroisoquinolin-4-ol
  参考文献：
  名称：

  Studies Directed to the Total Synthesis of ET 743 and Analogues Thereof:  An Expeditious Route to the ABFGH Subunit

  摘要：

  [GRAPHICS]In model studies directed to the total synthesis of Et743, a strategic S-C bond formation in systems 26 and 27 was demonstrated. It was further shown that Pictet-Spengler cyclization leading to spiro product 33 exhibits very high stereoselection.

  DOI：

  10.1021/ol016844k

文献信息

• Synthetic explorations in the saframycin-ecteinascidin series: construction of major chiral subunits through catalytic asymmetric induction
  作者：Bishan Zhou、Scott Edmondson、Juan Padron、Samuel J Danishefsky

  DOI：10.1016/s0040-4039(00)00105-2

  日期：2000.3

  The major subunits needed to reach the titled targets have been assembled by chemistry, which included p-Claisen rearrangement, asymmetric epoxidation and asymmetric dihydroxylation. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A novel face specific Mannich closure providing access to the saframycin-ecteinascidin series of piperazine based alkaloids
  作者：Bishan Zhou、Jinsong Guo、Samuel J Danishefsky

  DOI：10.1016/s0040-4039(00)00106-4

  日期：2000.3

  The Mannich-like closure of 10-->6 directly provides the backbone stereochemistry required for the titled alkaloids, in contrast to the stereochemical outcome in a related earlier case (3-->4). (C) 2000 Elsevier Science Ltd. All rights reserved.
• The Solution to a Deep Stereochemical Conundrum: Studies toward the Tetrahydroisoquinoline Alkaloids
  作者：Collin Chan、Shengping Zheng、Bishan Zhou、Jinsong Guo、Richard M. Heid、Benjamin J. D. Wright、Samuel J. Danishefsky

  DOI：10.1002/anie.200503982

  日期：2006.3.6
• Studies Directed to the Total Synthesis of ET 743 and Analogues Thereof:  An Expeditious Route to the ABFGH Subunit
  作者：Bishan Zhou、Jinsong Guo、Samuel J. Danishefsky

  DOI：10.1021/ol016844k

  日期：2002.1.1

  [GRAPHICS]In model studies directed to the total synthesis of Et743, a strategic S-C bond formation in systems 26 and 27 was demonstrated. It was further shown that Pictet-Spengler cyclization leading to spiro product 33 exhibits very high stereoselection.