(5R,10S)-7,9-Dibromo-8-methoxy-10-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonyloxy)-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carboxylic acid methyl ester | 876301-49-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5R,10S)-7,9-Dibromo-8-methoxy-10-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonyloxy)-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carboxylic acid methyl ester
• 英文别名: methyl (5R,6S)-7,9-dibromo-8-methoxy-6-[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]oxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxylate
• CAS: 876301-49-4
• 化学式: C₂₁H₂₃Br₂NO₈
• 分子量: 577.224
• InChiKey: TWSBIVAOVYBHQF-AKQDLLBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (5R,10S)-7,9-Dibromo-8-methoxy-10-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonyloxy)-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carboxylic acid methyl ester 在 caesium carbonate 作用下， 以 甲醇 为溶剂， 以95%的产率得到(5S*,6R*)-methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate
  参考文献：
  名称：

  （+）-hemifistularin 3的绝对立体化学的合成与归属

  摘要：

  对映体纯形式的海洋天然产物（+）-hemististularin 3的第一个全合成是通过使用（+）-螺杂恶唑啉酯与（+）-章鱼胺衍生物的酰胺形成反应完成的。在这项工作中采用的立体发散策略使得能够在（+）-hemifistularin 3的三个立体发生中心分配绝对构型。

  DOI：

  10.1016/j.tet.2014.07.049
• 作为产物：
  描述：

  (1S)-(-)-莰烷酰氯 、 (5S*,6R*)-methyl 7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro<4.5>deca-2,7,9-triene-3-carboxylate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到(5R,10S)-7,9-Dibromo-8-methoxy-10-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carbonyloxy)-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

  摘要：

  Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.097

文献信息

• Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative
  作者：Takahisa Ogamino、Rika Obata、Shigeru Nishiyama

  DOI：10.1016/j.tetlet.2005.11.097

  日期：2006.1

  Successful first synthesis of optically pure (+)- and (-)-aerothionins (1) from the racemic spiroisoxazoline derivative 8 has been accomplished. The absolute configuration of natural (+)-1 was determined by comparison of (+)- and (-)-8 with related derivatives. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and assignment of the absolute stereochemistry of (+)-hemifistularin 3
  作者：Hironori Kubo、Kaori Matsui、Tsuyoshi Saitoh、Shigeru Nishiyama

  DOI：10.1016/j.tet.2014.07.049

  日期：2014.9

  the marine natural product (+)-hemifistularin 3 in enantiomerically pure form was accomplished by using the amide forming reaction of (+)-spiroisoxazoline ester with the (+)-octopamine derivative. The stereodivergent strategy employed in this effort enabled the assignment of the absolute configurations at the three stereogenic centers in (+)-hemifistularin 3.

  对映体纯形式的海洋天然产物（+）-hemististularin 3的第一个全合成是通过使用（+）-螺杂恶唑啉酯与（+）-章鱼胺衍生物的酰胺形成反应完成的。在这项工作中采用的立体发散策略使得能够在（+）-hemifistularin 3的三个立体发生中心分配绝对构型。