phomolide B | 1263165-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: phomolide B
• 英文别名: (1R,3S,7S,8Z,10S)-7-hydroxy-3-propyl-4,11-dioxabicyclo[8.1.0]undec-8-en-5-one
• CAS: 1263165-16-7
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: VHLQBMDWATUSGI-ZUPRRRNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1R,3S,7S,8Z,10S)-7-[(4-methoxyphenyl)methoxy]-3-propyl-4,11-dioxabicyclo[8.1.0]undec-8-en-5-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以92%的产率得到phomolide B
  参考文献：
  名称：

  Total synthesis of Z-isomer of phomolide B

  摘要：

  We have achieved the synthesis of Z-isomer of phomolide B during our investigation toward the effect of protecting group on the outcome of ring-closing metathesis reaction. The other key reactions involved are cis-selective partial hydrogenation. Sharpless asymmetric epoxidation, Yamaguchi esteritication, and following 12 longest linear sequence with 18.5% overall yield starting from a known intermediate 20. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.003

文献信息

• Total synthesis of Z-isomer of phomolide B
  作者：Debendra K. Mohapatra、D. Prabhakar Reddy、Uttam Dash、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.11.003

  日期：2011.1

  We have achieved the synthesis of Z-isomer of phomolide B during our investigation toward the effect of protecting group on the outcome of ring-closing metathesis reaction. The other key reactions involved are cis-selective partial hydrogenation. Sharpless asymmetric epoxidation, Yamaguchi esteritication, and following 12 longest linear sequence with 18.5% overall yield starting from a known intermediate 20. (C) 2010 Elsevier Ltd. All rights reserved.