7-bromo-4a-methyl-4,4a,9,10-tetrahydro-3H-phenanthren-2-one | 909254-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 7-bromo-4a-methyl-4,4a,9,10-tetrahydro-3H-phenanthren-2-one
• 英文别名: (4aS)-7-bromo-4a-methyl-3,4,9,10-tetrahydrophenanthren-2-one
• CAS: 909254-06-4
• 化学式: C₁₅H₁₅BrO
• 分子量: 291.187
• InChiKey: ZBTKAJHVGZJQMK-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-bromo-4a-methyl-4,4a,9,10-tetrahydro-3H-phenanthren-2-one 在 sodium tetrahydroborate 、 高氯酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 0.17h， 生成 7-bromo-4a-methyl-1,2,3,4,4a,9-hexahydrophenanthren-2-ol
  参考文献：
  名称：

  Cholesterol Surrogates Incorporating a Benzophenone as Part of the Sterol Tetracycle

  摘要：

  Photoactivatable analogues 4-6 of cholesterol (1), having their cross-linking site in the ring D sterol region, have been synthesized starting from bromotetralone 14 via enantioselective Robinson annulation to enone 13 and Suzuki carbonylative coupling to the appropriate phenylboronic acid. Each of 4-6 was shown to substitute successfully for 1 in an assay of apo A-I-induced cellular cholesterol efflux, indicating that these analogues equilibrated with 1 in all major cellular pools.

  DOI：

  10.1021/jo060480y
• 作为产物：
  描述：

  6-溴-2-四氢萘酮 在 四氢吡咯 、 R(+)-alpha-甲基苄胺 、 对甲苯磺酸 作用下， 以 甲苯 、 苯 为溶剂， 反应 10.0h， 生成 7-bromo-4a-methyl-4,4a,9,10-tetrahydro-3H-phenanthren-2-one
  参考文献：
  名称：

  Cholesterol Surrogates Incorporating a Benzophenone as Part of the Sterol Tetracycle

  摘要：

  Photoactivatable analogues 4-6 of cholesterol (1), having their cross-linking site in the ring D sterol region, have been synthesized starting from bromotetralone 14 via enantioselective Robinson annulation to enone 13 and Suzuki carbonylative coupling to the appropriate phenylboronic acid. Each of 4-6 was shown to substitute successfully for 1 in an assay of apo A-I-induced cellular cholesterol efflux, indicating that these analogues equilibrated with 1 in all major cellular pools.

  DOI：

  10.1021/jo060480y

文献信息

• Cholesterol Surrogates Incorporating a Benzophenone as Part of the Sterol Tetracycle
  作者：Yonghong Gan、Thomas A. Spencer

  DOI：10.1021/jo060480y

  日期：2006.8.1

  Photoactivatable analogues 4-6 of cholesterol (1), having their cross-linking site in the ring D sterol region, have been synthesized starting from bromotetralone 14 via enantioselective Robinson annulation to enone 13 and Suzuki carbonylative coupling to the appropriate phenylboronic acid. Each of 4-6 was shown to substitute successfully for 1 in an assay of apo A-I-induced cellular cholesterol efflux, indicating that these analogues equilibrated with 1 in all major cellular pools.