((3S,5S)-7-Bromo-8-oxo-1-oxa-spiro[4.5]deca-6,9-dien-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester | 360577-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ((3S,5S)-7-Bromo-8-oxo-1-oxa-spiro[4.5]deca-6,9-dien-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester
• 英文别名: 9H-fluoren-9-ylmethyl N-[(3S,5S)-7-bromo-8-oxo-1-oxaspiro[4.5]deca-6,9-dien-3-yl]carbamate
• CAS: 360577-99-7
• 化学式: C₂₄H₂₀BrNO₄
• 分子量: 466.331
• InChiKey: MEOSMFDJIOLHSD-IZHWHUGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((3S,5S)-7-Bromo-8-oxo-1-oxa-spiro[4.5]deca-6,9-dien-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到((S)-5-Bromo-6-hydroxy-chroman-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis of spirodienone derivatives and their conversion into dihydrobenzopyrans

  摘要：

  The spirodienones 5, 6, and 12-14 including optically active ones were synthesized by anodic oxidation of the corresponding phenol derivatives. Although the asymmetric centers included in the substrates had little effect on the diastereomeric selectivity of the cyclization, the asymmetric structure of the products led to a regioselective conversion into dihydrobenzopyrans 16, 17, and 21-26 under mild Lewis acid-promoted conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00479-3
• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-3-bromo-L-tyrosinol 在 lithium perchlorate 、 sodium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 ((3S,5S)-7-Bromo-8-oxo-1-oxa-spiro[4.5]deca-6,9-dien-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis of spirodienone derivatives and their conversion into dihydrobenzopyrans

  摘要：

  The spirodienones 5, 6, and 12-14 including optically active ones were synthesized by anodic oxidation of the corresponding phenol derivatives. Although the asymmetric centers included in the substrates had little effect on the diastereomeric selectivity of the cyclization, the asymmetric structure of the products led to a regioselective conversion into dihydrobenzopyrans 16, 17, and 21-26 under mild Lewis acid-promoted conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00479-3

文献信息

• Synthesis of spirodienone derivatives and their conversion into dihydrobenzopyrans
  作者：Kazuki Mori、Shosuke Yamamura、Shigeru Nishiyama

  DOI：10.1016/s0040-4020(01)00479-3

  日期：2001.6

  The spirodienones 5, 6, and 12-14 including optically active ones were synthesized by anodic oxidation of the corresponding phenol derivatives. Although the asymmetric centers included in the substrates had little effect on the diastereomeric selectivity of the cyclization, the asymmetric structure of the products led to a regioselective conversion into dihydrobenzopyrans 16, 17, and 21-26 under mild Lewis acid-promoted conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.