(2S,4'aS,5'R,7'S,8'aR)-7-chloro-4,6,7'-trimethoxy-2',2',5'-trimethylspiro[1-benzofuran-2,6'-4,4a,5,7,8,8a-hexahydrobenzo[d][1,3]dioxine]-3-one | 118885-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (2S,4'aS,5'R,7'S,8'aR)-7-chloro-4,6,7'-trimethoxy-2',2',5'-trimethylspiro[1-benzofuran-2,6'-4,4a,5,7,8,8a-hexahydrobenzo[d][1,3]dioxine]-3-one
• CAS: 118885-00-0
• 化学式: C₂₁H₂₇ClO₇
• 分子量: 426.894
• InChiKey: KXAAXEKPHVHHQG-PQEFFMMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5'α-hydroxymethylgriseofulvin 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 copper(II) sulfate 作用下， 以 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 4.5h， 生成 (2S,4'aS,5'R,7'S,8'aR)-7-chloro-4,6,7'-trimethoxy-2',2',5'-trimethylspiro[1-benzofuran-2,6'-4,4a,5,7,8,8a-hexahydrobenzo[d][1,3]dioxine]-3-one
  参考文献：
  名称：

  Stereochemistry of transformation of 5'-formylgriseofulvin to 5'.ALPHA.-hydroxymethylgriseofulvin with a cell-free system of Streptomyces cinereocrocatus.

  摘要：

  The enzymatic hydrogenation of 5'-formylgriseofulvin (3a) with a cell-free system of Streptomyces cinereocrocatus afforded 5'α-hydroxymethylgriseofulvin (4a). The structure of 4a was determined by comparison of the proton nuclear magnetic resonance (1H-NMR) spectrum, mass spectrum (MS), circular dichroism (CD) and ultraviolet (UV) spectrum with those of 5'α- and 5'β-hydroxymethylgriseofulvin (4a and 5a) which were synthesized chemically. The stereochemistry of hydrogenation was unequivocally determined by 270 MHz 1H-NMR analysis of the acetonide (10b) which was derived from the product obtained by the enzymatic conversion of [7'-2H] 5'-formylgriseofulvin (3b)(Chart 3). The results clearly indicated that the 7'-pro-S-hydrogen of 4a originates from the 7'-hydrogen atom of the substrate (3a), and it was further proved that the 5'-βhydrogen of 4a originates from the medium by the use of deuterium oxide.

  DOI：

  10.1248/cpb.36.3878

文献信息

• ODA, TAIKO;SUEYOSHI, YUMIKO;HIROTA, KAORUKO;SATO, YOSHIHIRO, CHEM. AND PHARM. BULL., 36,(1988) N 10, C. 3878-3886
  作者：ODA, TAIKO、SUEYOSHI, YUMIKO、HIROTA, KAORUKO、SATO, YOSHIHIRO

  DOI：——

  日期：——