(2R)-2,3-dihydroxy-3-methyl-1-phenylbutan-1-one | 869698-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2,3-dihydroxy-3-methyl-1-phenylbutan-1-one
• CAS: 869698-92-0
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: WEAFPTAHDIOMGI-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2,3-dihydroxy-3-methyl-1-phenylbutan-1-one 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 (2R)-2,3-epoxy-3-methyl-1-phenylbutan-1-one
  参考文献：
  名称：

  Absolute Stereochemistry of Citrinadins A and B from Marine-Derived Fungus

  摘要：

  Citrinadin A (2) is a pentacyclic indolinone alkaloid isolated from the cultured broth of a fungus, Penicillium citrinum, which was separated from a marine red alga. The absolute stereochemistry of the pentacyclic core in 2 and its new congener, citrinadin B (1), was elucidated by analysis of the ROESY spectrum for the chlorohydrin derivative (3) of 1 as well as comparison of the electronic circular dichroism (ECD) spectra for 1 and 2 with those of known spirooxiindole alkaloids. On the other hand, the absolute configuration at C-21 bearing an epoxide ring was assigned as S by comparison of the vibrational circular dichroism (VCD) spectra of I with those of model compounds 2S- and 2R-2,3-epoxy-3,3-dimethyl-1-phenylpropan-1-one (4a and 4b, respectively).

  DOI：

  10.1021/jo051499o
• 作为产物：
  描述：

  3-甲基-1-苯基丁-2-烯-1-醇 在 potassium osmate(VI) manganese(IV) oxide 、 甲基磺酰胺 、 AD-mix-β 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 18.0h， 生成 (2R)-2,3-dihydroxy-3-methyl-1-phenylbutan-1-one
  参考文献：
  名称：

  Absolute Stereochemistry of Citrinadins A and B from Marine-Derived Fungus

  摘要：

  Citrinadin A (2) is a pentacyclic indolinone alkaloid isolated from the cultured broth of a fungus, Penicillium citrinum, which was separated from a marine red alga. The absolute stereochemistry of the pentacyclic core in 2 and its new congener, citrinadin B (1), was elucidated by analysis of the ROESY spectrum for the chlorohydrin derivative (3) of 1 as well as comparison of the electronic circular dichroism (ECD) spectra for 1 and 2 with those of known spirooxiindole alkaloids. On the other hand, the absolute configuration at C-21 bearing an epoxide ring was assigned as S by comparison of the vibrational circular dichroism (VCD) spectra of I with those of model compounds 2S- and 2R-2,3-epoxy-3,3-dimethyl-1-phenylpropan-1-one (4a and 4b, respectively).

  DOI：

  10.1021/jo051499o

文献信息

• Absolute Stereochemistry of Citrinadins A and B from Marine-Derived Fungus
  作者：Takao Mugishima、Masashi Tsuda、Yuu Kasai、Haruaki Ishiyama、Eri Fukushi、Jun Kawabata、Masayuki Watanabe、Kenichi Akao、Jun'ichi Kobayashi

  DOI：10.1021/jo051499o

  日期：2005.11.1

  Citrinadin A (2) is a pentacyclic indolinone alkaloid isolated from the cultured broth of a fungus, Penicillium citrinum, which was separated from a marine red alga. The absolute stereochemistry of the pentacyclic core in 2 and its new congener, citrinadin B (1), was elucidated by analysis of the ROESY spectrum for the chlorohydrin derivative (3) of 1 as well as comparison of the electronic circular dichroism (ECD) spectra for 1 and 2 with those of known spirooxiindole alkaloids. On the other hand, the absolute configuration at C-21 bearing an epoxide ring was assigned as S by comparison of the vibrational circular dichroism (VCD) spectra of I with those of model compounds 2S- and 2R-2,3-epoxy-3,3-dimethyl-1-phenylpropan-1-one (4a and 4b, respectively).