(20S)-7α-hydroxy-3-oxo-pregna-1,4-dien-20-carbaldehyde | 122197-36-8

• 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: (20S)-7α-hydroxy-3-oxo-pregna-1,4-dien-20-carbaldehyde
• 英文别名: (20S)-7alpha-hydroxy-3-oxo-pregna-1,4-dien-20-carbaldehyde；(2S)-2-[(7R,8S,9S,10R,13S,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]propanal
• CAS: 122197-36-8
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: XKNAFGDXOSIMKT-YHPPHIJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (20S)-7α-hydroxy-3-oxo-pregna-1,4-dien-20-carbaldehyde 在 盐酸 、 sodium borohydrid 作用下， 以 乙醇 、 甲苯 为溶剂， 以93%的产率得到(20S)-7α,21-dihydroxy-20-methyl-pregna-1,4-dien-3-one
  参考文献：
  名称：

  Process for the preparation of pregnane derivatives

  摘要：

  制备代表公式（V）的孕烷衍生物的方法，包括以下步骤：在氨或胺的存在下，将化合物（I）与碱（土）金属反应，得到代表公式（II）的化合物；保护所得化合物的羟基，得到代表公式（III）的化合物；保护所得化合物的3位羰基基团，得到代表公式（IV）的化合物；将所得化合物进行溶剂解，得到化合物（II）。

  公开号：

  US20030181742A1

文献信息

• 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。
• Processes for the preparation of steroid derivatives, intermediates therefor and processes for the preparation of the intermediates
  申请人：Kuraray Co., Ltd.

  公开号：US06310225B1

  公开（公告）日：2001-10-30

  Steroid derivatives useful as intermediates for producing vitamin D derivates as well as processes for producing the steroid derivatives are provided. The steroid derivatives include halide compounds represented by the following formulae: wherein X, R1 and R2 are as defined by the specification.

  提供用作生产维生素D衍生物中间体的类固醇衍生物以及生产类固醇衍生物的过程。该类固醇衍生物包括以下式子所表示的卤化物化合物：其中X，R1和R2由规范定义。
• 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。
• PROCESSES FOR THE PREPARATION OF STEROID DERIVATIVES, INTERMEDIATES THEREFOR AND PROCESSES FOR THE PREPARATION OF THE INTERMEDIATES
  申请人：Kuraray Co., Ltd.

  公开号：EP1081157A1

  公开（公告）日：2001-03-07

  Steroid derivatives useful as the intermediate for preparing vitamin D derivatives such as 1α, 25-dihydroxyvitamin D3 and 2β-(3-hydroxypropoxy)-1α, 25-dihydroxyvitamin D3, i.e., halides of general formula (II) (wherein X is bromo or iodo); 1,4,6-trien-3-one compounds of general formula (III) (wherein X is as defined above); 1,3,5,7-tetraene compounds of general formula (IV) (wherein X is as defined above; and R1 is acyl); and 1,5,7-triene compounds of general formula (V) (wherein X is as defined above; and R2 is hydrogen or a hydroxyl-protecting group); and processes for the preparation of the same.

  可用作制备维生素 D 衍生物如 1α，25-二羟基维生素 D3 和 2β-（3-羟基丙氧基）-1α，25-二羟基维生素 D3 的中间体的类固醇衍生物，即通式（II）的卤化物（其中 X 为溴或碘）；通式（III）的 1,4,6-三烯-3-酮化合物（其中 X 如上所定义）；通式（IV）的 1,3,5,7-四烯化合物（其中 X 如上所定义；R1 为酰基）；以及通式（V）的 1,5,7-三烯化合物（其中 X 如上所定义；R2 为氢或羟基保护基）；以及制备上述物质的工艺。
• METHOD FOR PRODUCING 5ALPHA-PREGNANE DERIVATIVE
  申请人：Kuraray Co., Ltd.

  公开号：EP1743902A1

  公开（公告）日：2007-01-17

  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 R1 is a hydroxyl-protecting group, and R2, R11 and R12 are each independently a hydrogen atom or a hydroxyl-protecting group and R3 and R4 are each hydrogen atoms in combination form a bond.

  本发明涉及一种生产由式(II)表示的5α-孕烷衍生物的方法，其特征在于由式(I)表示的孕烷衍生物与选自碱金属和碱土金属的金属在质子供体和胺和/或氨的存在下反应。根据本发明，可以提供一种利用容易获得的原料高产率地生产可用作角鲨胺合成中间体的 5α 孕烷衍生物的方法： 其中 R1 是羟基保护基团，R2、R11 和 R12 各自独立地为氢原子或羟基保护基团，R3 和 R4 各自为氢原子，三者结合成键。