5,6β-cyclopropano-5β-androsta-3,17-dione | 38022-56-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 5,6β-cyclopropano-5β-androsta-3,17-dione
• 英文别名: (1S,2R,7S,9S,11R,12S,16S)-2,16-dimethylpentacyclo[9.7.0.02,7.07,9.012,16]octadecane-5,15-dione
• CAS: 38022-56-9
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: JFFYTDKXDTWDTC-JQMFHEMUSA-N

物化性质

• 沸点：
  431.4±38.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6β-cyclopropano-5β-androsta-3,17-dione 在 Mycobacterium sp. (NRRL B-3805) 、 Nutrient broth-dextrose medium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以4%的产率得到雄烯二酮
  参考文献：
  名称：

  Microbial transformation of 3-hydroxy-5,6-cyclopropanocholestanes - An alternative route to 6-methylsteroids

  摘要：

  Incubation of 3 beta -hydroxy-5,6 beta alpha cyclopropano-5 alpha -cholestane (4), 3 beta -hydroxy-5,6 beta -cyclopropano-5 beta -cholestane (5), and 3 beta -hydroxy-5,6 alpha -cyclopropano-5 alpha -cholest-7-ene (6) with Mycobacterium sp. (NRRL B-3805) gave a mixture of side chain cleaved 17-keto steroids as the major products in 52, 57, and 69% yields, respectively. Among these 17-keto steroids, the cyclopropyl ring eliminated product, androst-4-ene-3,17-dione (9), was isolated in 6, 4, and 8% yields, respectively. A cyclopropyl ring migration product, 6 alpha ,7 alpha -cyclopro-panoandrost-4-ene-3,17-dione (16), was isolated from the incubation mixture of 6 in 4% yield, also 10% yield of 16 was obtained when 5,6 alpha -cyclopropano-5 alpha -androst-7-ene-3, 17-dione (12) was incubated. The cyclopropyl ring opening and subsequent reduction followed by oxidation of the two major biotransformation products, 5,6 beta -cyclopropano-5 beta -androsta-3, 17-dione (10) and 5,6 alpha -cyclopropano-5 alpha -androsta-3,17-dione (7), gave 6 beta- and 6 alpha -methylandrost-4-ene-3,17-dione in 60, and 45% yields, respectively. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00170-7
• 作为产物：
  描述：

  胆固醇 在 Mycobacterium sp. (NRRL B-3805) 、 Nutrient broth-dextrose medium 、 diethylzinc 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 312.0h， 生成 5,6β-cyclopropano-5β-androsta-3,17-dione
  参考文献：
  名称：

  Microbial transformation of 3-hydroxy-5,6-cyclopropanocholestanes - An alternative route to 6-methylsteroids

  摘要：

  Incubation of 3 beta -hydroxy-5,6 beta alpha cyclopropano-5 alpha -cholestane (4), 3 beta -hydroxy-5,6 beta -cyclopropano-5 beta -cholestane (5), and 3 beta -hydroxy-5,6 alpha -cyclopropano-5 alpha -cholest-7-ene (6) with Mycobacterium sp. (NRRL B-3805) gave a mixture of side chain cleaved 17-keto steroids as the major products in 52, 57, and 69% yields, respectively. Among these 17-keto steroids, the cyclopropyl ring eliminated product, androst-4-ene-3,17-dione (9), was isolated in 6, 4, and 8% yields, respectively. A cyclopropyl ring migration product, 6 alpha ,7 alpha -cyclopro-panoandrost-4-ene-3,17-dione (16), was isolated from the incubation mixture of 6 in 4% yield, also 10% yield of 16 was obtained when 5,6 alpha -cyclopropano-5 alpha -androst-7-ene-3, 17-dione (12) was incubated. The cyclopropyl ring opening and subsequent reduction followed by oxidation of the two major biotransformation products, 5,6 beta -cyclopropano-5 beta -androsta-3, 17-dione (10) and 5,6 alpha -cyclopropano-5 alpha -androsta-3,17-dione (7), gave 6 beta- and 6 alpha -methylandrost-4-ene-3,17-dione in 60, and 45% yields, respectively. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00170-7

文献信息

• Microbial transformation of 3-hydroxy-5,6-cyclopropanocholestanes - An alternative route to 6-methylsteroids
  作者：Jiann-Long Yan、Shoei-Sheng Lee、K.C. Wang

  DOI：10.1016/s0039-128x(00)00170-7

  日期：2000.12

  Incubation of 3 beta -hydroxy-5,6 beta alpha cyclopropano-5 alpha -cholestane (4), 3 beta -hydroxy-5,6 beta -cyclopropano-5 beta -cholestane (5), and 3 beta -hydroxy-5,6 alpha -cyclopropano-5 alpha -cholest-7-ene (6) with Mycobacterium sp. (NRRL B-3805) gave a mixture of side chain cleaved 17-keto steroids as the major products in 52, 57, and 69% yields, respectively. Among these 17-keto steroids, the cyclopropyl ring eliminated product, androst-4-ene-3,17-dione (9), was isolated in 6, 4, and 8% yields, respectively. A cyclopropyl ring migration product, 6 alpha ,7 alpha -cyclopro-panoandrost-4-ene-3,17-dione (16), was isolated from the incubation mixture of 6 in 4% yield, also 10% yield of 16 was obtained when 5,6 alpha -cyclopropano-5 alpha -androst-7-ene-3, 17-dione (12) was incubated. The cyclopropyl ring opening and subsequent reduction followed by oxidation of the two major biotransformation products, 5,6 beta -cyclopropano-5 beta -androsta-3, 17-dione (10) and 5,6 alpha -cyclopropano-5 alpha -androsta-3,17-dione (7), gave 6 beta- and 6 alpha -methylandrost-4-ene-3,17-dione in 60, and 45% yields, respectively. (C) 2000 Elsevier Science Inc. All rights reserved.