(7α)-3-ketobisnorchol-4-ene-7,22-diol | 77530-51-9

• 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: (7α)-3-ketobisnorchol-4-ene-7,22-diol
• 英文别名: (20S)-7α,21-dihydroxy-20-methyl-pregn-4-en-3-one；(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-17-[(2S)-1-hydroxypropan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 77530-51-9
• 化学式: C₂₂H₃₄O₃
• 分子量: 346.51
• InChiKey: KHAASJIVTYLGID-YHPPHIJISA-N

物化性质

• 沸点：
  504.2±33.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (7α)-3-ketobisnorchol-4-ene-7,22-diol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 platinum on activated charcoal sodium hypochlorite 、 三甲基氯硅烷 、 硼烷四氢呋喃络合物 、 氨 、 氢气 、 lithium 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 、 sodium bromide 、 sodium t-butanolate 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， -20.0~24.0 ℃ 、344.75 kPa 条件下， 反应 46.42h， 生成 (5S,7R,8R,9S,10S,13R,14S,17R)-7-羟基-17-((2R,5R)-5
  参考文献：
  名称：

  A Short Formal Synthesis of Squalamine from a Microbial Metabolite

  摘要：

  [GRAPHICS]A short formal synthesis of squalamine is described, utilizing the biotransformation product 2, which is available in one step from commercially available 3-keto-23,24-bisnorchol-4-en-22-ol (1), Regioselective C-22 oxidation and C-24 sulfation of the corresponding alcohols in the presence of a free C-7 alcohol make for an efficient preparation of squalamine intermediate 11.

  DOI：

  10.1021/ol0059495
• 作为产物：
  描述：

  (20S)-21-羟基-20-甲基孕甾-4-烯-3-酮 在 葡萄糖 、 Diplodia gossypina (ATCC 20576) 、 氧气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以155 mg的产率得到(7α)-3-ketobisnorchol-4-ene-7,22-diol
  参考文献：
  名称：

  A Short Formal Synthesis of Squalamine from a Microbial Metabolite

  摘要：

  [GRAPHICS]A short formal synthesis of squalamine is described, utilizing the biotransformation product 2, which is available in one step from commercially available 3-keto-23,24-bisnorchol-4-en-22-ol (1), Regioselective C-22 oxidation and C-24 sulfation of the corresponding alcohols in the presence of a free C-7 alcohol make for an efficient preparation of squalamine intermediate 11.

  DOI：

  10.1021/ol0059495

文献信息

• 7Alpha-hydroxypregn-4-en-3-one-20-carbaldehyde, process for producing the same, and process for producing 7alpha,21-dihydroxy-20-methylpregn-4-en-3-one from the same
  申请人：——

  公开号：US20040236126A1

  公开（公告）日：2004-11-25

  7&agr;-Hydroxy-pregn-4-en-3-one-20-carbaldehyde, a production method thereof and a method for producing 7&agr;,21-dihydroxy-20-methyl-pregn-4-en-3-one, which is useful as a synthetic intermediate for pharmaceuticals such as squalamine and the like, efficiently at high purity from the carbaldehyde.

  7α-羟基孕-4-烯-3-酮-20-醛及其制备方法以及用作合成类似于鲨烷等药物的中间体7α，21-二羟基-20-甲基孕-4-烯-3-酮的高效纯化方法，从醛中高效纯化。
• 7α-hydroxy-pregn-4-en-3-one-20-carbaldehyde, process for producing the same, and process for producing 7α, 21-dihydroxy-20-methyl-pregn-4-en-3-one from the same
  申请人：Kuraray Co., Ltd.

  公开号：US07153988B2

  公开（公告）日：2006-12-26

  7α-Hydroxy-pregn-4-en-3-one-20-carbaldehyde, a production method thereof and a method for producing 7α,21 -dihydroxy-20-methyl-pregn-4-en-3-one, which is useful as a synthetic intermediate for pharmaceuticals such as squalamine and the like, efficiently at high purity from the carbaldehyde.

  7α-羟基孕-4-烯-3-酮-20-羧醛及其生产方法以及用于制备药物如鲨烷等的合成中间体7α,21-双羟基-20-甲基孕-4-烯-3-酮的生产方法，能够从羧醛中高效纯度地制得。
• Method for producing 5alpha-pregnane derivative
  申请人：Sugioka Takashi

  公开号：US20070149494A1

  公开（公告）日：2007-06-28

  The present invention relates to a method of producing 5α-pregnane derivatives represented by the formula (II), which is characterized by reacting a pregnane derivative represented by the formula (I) with a metal selected from alkali metals and alkaline earth metals in the presence of a proton donor and an amine and/or ammonia. According to the present invention, a method capable of producing 5α-pregnane derivatives useful as synthetic intermediates for squalamine, in a high yield from easily available raw materials, can be provided: wherein R 1 is a hydroxyl-protecting group, and R 2 , R 11 and R 12 are each independently a hydrogen atom or a hydroxyl-protecting group and R 3 and R 4 are each hydrogen atoms in combination form a bond.

  本发明涉及一种制备式（II）所表示的5α-孕烷衍生物的方法，其特征在于在质子给体和胺和/或氨的存在下，用碱金属和碱土金属中选择的一种金属与式（I）所表示的孕烷衍生物反应。根据本发明，可以提供一种能够从易得的原料中高产得到用作鲨烯合成中间体的5α-孕烷衍生物的方法。其中R1是一个羟基保护基，R2、R11和R12各自独立地是氢原子或羟基保护基，R3和R4在组合时形成一个键，且各自是氢原子。
• Method for Producing 5Alpha-Pregnane Derivative
  申请人：Koyakumaru Kenichi

  公开号：US20070203106A1

  公开（公告）日：2007-08-30

  The present invention relates to a method of producing 5α-pregnane derivatives represented by the formula (III), which is characterized by selectively reducing a carbon-carbon double bond of a 5α-pregnane derivative represented by the formula (II) in a mixture of 5α-pregnane derivatives represented by the formula (I) and the formula (II). According to the present invention, a method capable of producing 5α-pregnane derivatives useful as synthetic intermediates for squalamine, in a high yield from easily available raw materials, can be provided: wherein R 1 , R 2 , R 11 and R 12 are each independently a hydrogen atom or a hydroxyl-protecting group.

  本发明涉及一种生产5α-孕烷衍生物的方法，其表示为公式(III)，其特征在于在公式(I)和公式(II)的5α-孕烷衍生物混合物中，选择性地还原公式(II)中的碳-碳双键。根据本发明，可以提供一种能够从易得到的原料中高产得到用作鲨烷合成中间体的5α-孕烷衍生物的方法。其中，R1、R2、R11和R12各自独立地表示氢原子或羟基保护基。
• 7A-HYDROXYPREGN-4-EN-3-ONE-20-CARBALDEHYDE, PROCESS FOR PRODUCING THE SAME AND PROCESS FOR PRODUCING 7A,21-DIHYDROXY-20-METHYLPREGN-4-EN-3-ONE FROM THE SAME
  申请人：Kuraray Co., Ltd.

  公开号：EP1431395A1

  公开（公告）日：2004-06-23

  7α-Hydroxy-pregn-4-en-3-one-20-carbaldehyde, a production method thereof and a method for producing 7α,21-dihydroxy-20-methyl-pregn-4-en-3-one, which is useful as a synthetic intermediate for pharmaceuticals such as squalamine and the like, efficiently at high purity from the carbaldehyde.

  7α-羟基-孕甾-4-烯-3-酮-20-甲醛、其生产方法以及从甲醛中高效、高纯度地生产 7α,21-二羟基-20-甲基-孕甾-4-烯-3-酮的方法，7α,21-二羟基-20-甲基-孕甾-4-烯-3-酮可用作药物（如角鲨胺等）的合成中间体。