1-[(5-bromo(2H-benzo[d]1,3-dioxolan-4-yl))methoxy]-1,1,2,2-tetramethyl-1-silapropane | 669051-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-[(5-bromo(2H-benzo[d]1,3-dioxolan-4-yl))methoxy]-1,1,2,2-tetramethyl-1-silapropane
• 英文别名: ((5-bromobenzo[d][1,3]dioxol-4-yl)methoxy)(tert-butyl)dimethylsilane；(5-Bromo-1,3-benzodioxol-4-yl)methoxy-tert-butyl-dimethylsilane；(5-bromo-1,3-benzodioxol-4-yl)methoxy-tert-butyl-dimethylsilane
• CAS: 669051-29-0
• 化学式: C₁₄H₂₁BrO₃Si
• 分子量: 345.308
• InChiKey: WJILCHZSXLNMOW-UHFFFAOYSA-N

物化性质

• 熔点：
  40.5-42.0 °C
• 沸点：
  352.2±42.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  1-[(5-bromo(2H-benzo[d]1,3-dioxolan-4-yl))methoxy]-1,1,2,2-tetramethyl-1-silapropane 在 palladium diacetate 、 正丁基锂 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.58h， 生成 2-methoxy-5-{4-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]-(2H-benzo[d]1,3-dioxolen-5-yl)}cyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  Practical synthesis of biaryl colchicinoids containing 3′,4′-catechol ether-based A-rings via Suzuki cross-coupling with ligandless palladium in water

  摘要：

  Eight new biaryl colchicinoids containing 3',4'-methylene or benzodioxy ether bridges were synthesized. The key synthetic step employed a ligandless, aqueous Suzuki cross-coupling reaction catalyzed by Pd(OAc)(2) with tetrabutylammonium bromide (TBAB) and potassium carbonate (K2CO3). The biaryl Suzuki products were typically formed in 5-30 min and always in less than 1 h. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.016
• 作为产物：
  描述：

  1,3-苯并二氧戊环-4-烷基甲醇 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 TEA 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-[(5-bromo(2H-benzo[d]1,3-dioxolan-4-yl))methoxy]-1,1,2,2-tetramethyl-1-silapropane
  参考文献：
  名称：

  Practical synthesis of biaryl colchicinoids containing 3′,4′-catechol ether-based A-rings via Suzuki cross-coupling with ligandless palladium in water

  摘要：

  Eight new biaryl colchicinoids containing 3',4'-methylene or benzodioxy ether bridges were synthesized. The key synthetic step employed a ligandless, aqueous Suzuki cross-coupling reaction catalyzed by Pd(OAc)(2) with tetrabutylammonium bromide (TBAB) and potassium carbonate (K2CO3). The biaryl Suzuki products were typically formed in 5-30 min and always in less than 1 h. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.016

文献信息

• Enantioselective Divergent Syntheses of (+)-Bulleyanaline and Related Isoquinoline Alkaloids from the Genus <i>Corydalis</i>
  作者：Barry M. Trost、Chao-I Joey Hung、Zhiwei Jiao

  DOI：10.1021/jacs.9b08441

  日期：2019.10.9

  The isoquinoline alkaloids isolated from the genus Corydalis possess potent and diverse biological activities. Herein, a concise, divergent, and enantioselective route to access these natural products is disclosed. Key transformations of our approach include a challenging Zn-ProPhenol catalyzed asymmetric Mannich reaction to build a quaternary stereogenic center and a rapid cationic Au-catalyzed cycloisomerization

  从延胡索属中分离出的异喹啉生物碱具有强大而多样的生物活性。在此，公开了获取这些天然产物的简明、发散和对映选择性途径。我们方法的关键转变包括具有挑战性的 Zn-ProPhenol 催化的不对称曼尼希反应以构建四元立体中心和快速阳离子 Au 催化的环异构化到这些天然产物的共同结构骨架。随后的后期氧化和修饰可以有效地获取目标生物碱。总体而言，从易得的起始材料中，通过 6 到 10 步成功合成了 7 种天然产物，包括 (+)-corynoline、(+)-anhydrocorynoline、(+)-12-hydroxycorynoline、(+)-12-hydroxycorynoline，（ +)-棒碱，(+)-6-乙酰基棒碱，
• Practical synthesis of biaryl colchicinoids containing 3′,4′-catechol ether-based A-rings via Suzuki cross-coupling with ligandless palladium in water
  作者：Amy Morin Deveau、Timothy L. Macdonald

  DOI：10.1016/j.tetlet.2003.11.016

  日期：2004.1

  Eight new biaryl colchicinoids containing 3',4'-methylene or benzodioxy ether bridges were synthesized. The key synthetic step employed a ligandless, aqueous Suzuki cross-coupling reaction catalyzed by Pd(OAc)(2) with tetrabutylammonium bromide (TBAB) and potassium carbonate (K2CO3). The biaryl Suzuki products were typically formed in 5-30 min and always in less than 1 h. (C) 2003 Elsevier Ltd. All rights reserved.