(3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione | 26478-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione
• 英文别名: (3aS,7aR)-2-[2-(3,4-dimethoxyphenyl)ethyl]hexahydroisoindole-1,3-dione；(3aR,7aS)-rel-2-[2-(3,4-dimethoxyphenyl)ethyl]hexahydro-1H-isoindole-1,3(2H)-dione；2-(3,4-dimethoxy-phenethyl)-(3ar,7ac)-hexahydro-isoindole-1,3-dione；2-(3,4-Dimethoxy-phenaethyl)-(3ar,7ac)-hexahydro-isoindol-1,3-dion；(3aS,7aR)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
• CAS: 26478-05-7
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: OVMAGPIZKWWEQY-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione 在 甲烷磺酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 2,3-dimethoxy-12b-(trifluoromethyl)-5,6,8a,9,10,11,12,12a-octahydroisoindolo[1,2-a]isoquinolin-8(12bH)-one
  参考文献：
  名称：

  One-Pot Cascade Trifluoromethylation/Cyclization of Imides: Synthesis of α-Trifluoromethylated Amine Derivatives

  摘要：

  Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the alpha-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.

  DOI：

  10.1021/jo5002998
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 (3aSR,7aRS)-2-[2-(3,4-dimethoxyphenyl)ethyl]-hexahydro-isoindole-1,3-dione
  参考文献：
  名称：

  The use of interlocked ‘customised’ blade plates in the treatment of metaphyseal fractures in patients with poor bone stock

  摘要：

  Balanced and stable fixation in metaphyseal fractures and nonunion can be difficult because of osteoporosis, disuse osteopenia, comminution, joint proximity or malignant infiltration. Five patients with nonunion and four with comminuted or pathological acute fractures of metaphyseal areas of the tibia or humerus were treated with a 'customised' interlocked blade plate. The plates are standard AO dynamic compression plates of a suitable length that are bent to an acute angle in an industrial vice and 'interlocked'. The nine patients with a mean age of 62.2 years (range 30-91) were followed up for a mean of 7.2 months.At follow-up all fractures had healed with a single complication of subacromial impingement in a patient with a proximal humeral fracture. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0020-1383(99)00278-8

文献信息

• Asymmetric Total Synthesis of the Proposed Structure of the Medicinal Alkaloid Jamtine Using the Chiral Base Approach
  作者：Nigel S. Simpkins、Christopher D. Gill

  DOI：10.1021/ol027447s

  日期：2003.2.1

  [GRAPHICS]A highly step-economic asymmetric synthesis of the tetracyclic structure assigned to the medicinal alkaloid jamtine has been accomplished using a chiral lithium amide base desymmetrization of a ring-fused imide. The structure synthesized appears to be different from that of the natural product originally reported.
• CHIRAL LITHIUM AMIDE BASE DESYMMETRIZATION OF A RING FUSED IMIDE: FORMATION OF (3aS,7aS)-2-[2-(3,4-DIMETHOXYPHENYL)-ETHYL]-1,3-DIOXO-OCTAHYDRO-ISOINDOLE-3a-CARBOXYLIC ACID METHYL ESTER
  作者：Rodeschini, Vincent、Simpkins, Nigel S.、Zhang, Fengzhi、Beenen, Melissa A.、Ellman, Jonathan A.

  DOI：10.15227/orgsyn.084.0306

  日期：——
• Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine
  作者：Christopher D Gill、Daniel A Greenhalgh、Nigel S Simpkins

  DOI：10.1016/j.tet.2003.08.046

  日期：2003.11

  The synthesis of the alkaloid jamtine and the antidepressant paroxetine have been addressed by a strategy involving asymmetric desymmetrisation of prochiral imides by a chiral lithium amide base. A short reaction sequence, starting with a cyclohexane fused succinimide, led to the structures originally reported for the alkaloid jamine and its derived N-oxide. The structures synthesised are shown not to correspond with those originally reported. A second sequence involves desymmetrisation of a 4-arylglutarimide, and provides a short enantioselective synthesis of the drug substance paroxetine. (C) 2003 Elsevier Ltd. All rights reserved.
• The use of interlocked ‘customised’ blade plates in the treatment of metaphyseal fractures in patients with poor bone stock
  作者：S.H. Palmer、R. Handley、K. Willett

  DOI：10.1016/s0020-1383(99)00278-8

  日期：2000.4

  Balanced and stable fixation in metaphyseal fractures and nonunion can be difficult because of osteoporosis, disuse osteopenia, comminution, joint proximity or malignant infiltration. Five patients with nonunion and four with comminuted or pathological acute fractures of metaphyseal areas of the tibia or humerus were treated with a 'customised' interlocked blade plate. The plates are standard AO dynamic compression plates of a suitable length that are bent to an acute angle in an industrial vice and 'interlocked'. The nine patients with a mean age of 62.2 years (range 30-91) were followed up for a mean of 7.2 months.At follow-up all fractures had healed with a single complication of subacromial impingement in a patient with a proximal humeral fracture. (C) 2000 Elsevier Science Ltd. All rights reserved.
• One-Pot Cascade Trifluoromethylation/Cyclization of Imides: Synthesis of α-Trifluoromethylated Amine Derivatives
  作者：Vinay Kumar Pandey、Pazhamalai Anbarasan

  DOI：10.1021/jo5002998

  日期：2014.5.2

  Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the alpha-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.