(2S,3aS,7aS)-4-bromo-2-(4-methoxyphenyl)-3a,7a-dihydro-1,3-benzodioxole | 1035055-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3aS,7aS)-4-bromo-2-(4-methoxyphenyl)-3a,7a-dihydro-1,3-benzodioxole
• CAS: 1035055-69-6
• 化学式: C₁₄H₁₃BrO₃
• 分子量: 309.159
• InChiKey: PMOZBAUKIZBCDH-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3aS,7aS)-4-bromo-2-(4-methoxyphenyl)-3a,7a-dihydro-1,3-benzodioxole 在 四氧化锇 、 N-甲基吲哚酮 作用下， 生成 (2S,3aS,4R,5R,7aS)-7-bromo-2-(4-methoxyphenyl)-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol
  参考文献：
  名称：

  A chemoenzymatic total synthesis of ent-narciclasine

  摘要：

  The synthesis of the title compound [(-)-1] has been achieved, for the first time, by reacting the aryl boronic acid ester 4 with the amino-conduritol derivative 6 under Suzuki-Miyaura cross-coupling conditions then subjecting the product phenanthridinone 23 to a global deprotection process using trimethylsilyl bromide. The aromatic building block 4 was prepared in ten steps from piperonal while compound 6 was obtained in nine steps from the enantiomerically pure cis-1,2-dihydrocatechol 7. This last compound is available, in multi-gram quantities, through a whole-cell-mediated biotransformation of bromobenzene using genetically engineered organisms that over-express the responsible enzyme, namely toluene dioxygenase. Since the enantiomer of compound 7 is available by related means, the present work also represents a formal total synthesis of the alkaloid narciclasine [(+)-1]. The single-crystal X-ray analysis of compound 13 is reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.113
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 、 (1S-顺式)-3-溴-3,5-环己二烯-1,2-二醇 在 D(+)-10-樟脑磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以80%的产率得到(2S,3aS,7aS)-4-bromo-2-(4-methoxyphenyl)-3a,7a-dihydro-1,3-benzodioxole
  参考文献：
  名称：

  The Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin

  摘要：

  将对映体纯度较高的顺式-1,2-二氢邻苯二酚 10 转化为环己酮 17a 的反应顺序为七个步骤。使用相同的起始原料，以近乎等效的顺序合成了对映体系统 17b。化合物 17a 与ent-viridin（ent-1）的 A 环有关，ent-1 是呋喃类病毒素（1）的非天然对映体。

  DOI：

  10.1071/ch09283

文献信息

• A chemoenzymatic synthesis of the anti-influenza agent Tamiflu®
  作者：Maria Matveenko、Anthony C. Willis、Martin G. Banwell

  DOI：10.1016/j.tetlet.2008.09.130

  日期：2008.12

  The anti-influenza drug Tamiflu (R) is synthesized from enzymatically derived, enantiomerically pure, and readily available cis-1,2-dihydrocatechol. (C) 2008 Elsevier Ltd. All rights reserved.
• A chemoenzymatic total synthesis of ent-narciclasine
  作者：Maria Matveenko、Martin G. Banwell、Anthony C. Willis

  DOI：10.1016/j.tet.2008.01.113

  日期：2008.5

  The synthesis of the title compound [(-)-1] has been achieved, for the first time, by reacting the aryl boronic acid ester 4 with the amino-conduritol derivative 6 under Suzuki-Miyaura cross-coupling conditions then subjecting the product phenanthridinone 23 to a global deprotection process using trimethylsilyl bromide. The aromatic building block 4 was prepared in ten steps from piperonal while compound 6 was obtained in nine steps from the enantiomerically pure cis-1,2-dihydrocatechol 7. This last compound is available, in multi-gram quantities, through a whole-cell-mediated biotransformation of bromobenzene using genetically engineered organisms that over-express the responsible enzyme, namely toluene dioxygenase. Since the enantiomer of compound 7 is available by related means, the present work also represents a formal total synthesis of the alkaloid narciclasine [(+)-1]. The single-crystal X-ray analysis of compound 13 is reported. (C) 2008 Elsevier Ltd. All rights reserved.
• The Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin
  作者：Alison D. Findlay、Antje Gebert、Ian A. Cade、Martin G. Banwell

  DOI：10.1071/ch09283

  日期：——

  A seven-step reaction sequence has been used to convert the enantiomerically pure cis-1,2-dihydrocatechol 10 into the cyclohexenone 17a. A near equivalent sequence involving the same starting material has allowed for the synthesis of the regioisomeric system 17b. Compound 17a is related to the A-ring of ent-viridin (ent-1), the non-natural enantiomer of the furanosteroid viridin (1).

  将对映体纯度较高的顺式-1,2-二氢邻苯二酚 10 转化为环己酮 17a 的反应顺序为七个步骤。使用相同的起始原料，以近乎等效的顺序合成了对映体系统 17b。化合物 17a 与ent-viridin（ent-1）的 A 环有关，ent-1 是呋喃类病毒素（1）的非天然对映体。