7α-hydroxypregna-1,4-dien-3-one-20-carbaldehyde | 177698-17-8

• 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: 7α-hydroxypregna-1,4-dien-3-one-20-carbaldehyde
• 英文别名: 7-Hydroxy-pregna-1,4-dien-3-one-20-carbaldehyde；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: 177698-17-8
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: XKNAFGDXOSIMKT-FNTUIYCDSA-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：

  7α-hydroxypregna-1,4-dien-3-one-20-carbaldehyde 、 2,2-二甲基-1,3-丙二醇 在 molecular sieve 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到20-(5,5-dimethyl-1,3-dioxan-2-yl)-7α-hydroxypregna-1,4-dien-3-one
  参考文献：
  名称：

  Pregnane derivatives and processes for production thereof

  摘要：

  提供的孕烷衍生物由以下式表示##STR1##其中A.sup.1代表氢原子或羟基，A.sup.2代表取代基，例如当A.sup.1代表氢原子时，A.sup.2代表羟基，或者当A.sup.1代表羟基时，A.sup.2代表氢原子，或者A.sup.1和A.sup.2结合在一起形成酮基；D.sup.1代表取代基，例如羟基，D.sup.2代表氢原子，或者D.sup.1和D.sup.2结合在一起形成环氧基或单键；D.sup.3，D.sup.5和D.sup.7分别代表氢原子，D.sup.4代表羟基，D.sup.6代表取代基，例如羟基，或者D.sup.3和D.sup.4可以结合在一起形成环氧基或单键，或者D.sup.4和D.sup.5可以结合在一起形成单键，或者D.sup.5和D.sup.6可以结合在一起形成环氧基或单键，或者D.sup.6和D.sup.7可以结合在一起形成单键；X.sup.1和X.sup.2分别代表较低的烷氧基，或者当它们结合在一起时，它们代表较低的烷二氧基或酮基，以及它们的制备方法。这些孕烷衍生物可用作合成具有1α-位羟基的维生素D.sub.3衍生物的中间体。

  公开号：

  US05112998A1
• 作为产物：
  描述：

  鹅去氧胆酸 、 sodium hydroxide 、 水 在 甲醇 、 水 作用下， 反应 72.0h， 以to give 0.77 g of 7α-hydroxypregna-1,4-dien-3-one-20 -carbaldehyde的产率得到7α-hydroxypregna-1,4-dien-3-one-20-carbaldehyde
  参考文献：
  名称：

  Pregnane derivatives and processes for production thereof

  摘要：

  提供了由公式##STR1##表示的孕酮衍生物，其中A.sup.1表示氢原子或羟基，A.sup.2表示取代基，例如当A.sup.1表示氢原子时，A.sup.2表示羟基，或当A.sup.1表示羟基时，A.sup.2表示氢原子，或A.sup.1和A.sup.2结合形成酮基；D.sup.1表示取代基，例如羟基，D.sup.2表示氢原子，或D.sup.1和D.sup.2结合形成环氧基或单键；D.sup.3，D.sup.5和D.sup.7各表示氢原子，D.sup.4表示羟基，D.sup.6表示取代基，例如羟基，或D.sup.3和D.sup.4可以结合形成环氧基或单键，或D.sup.4和D.sup.5可以结合形成单键，或D.sup.5和D.sup.6可以结合形成环氧基或单键，或D.sup.6和D.sup.7可以结合形成单键；X.sup.1和X.sup.2各表示较低的烷氧基，或当它们结合在一起时，它们表示较低的烷二氧基或酮基。还提供了一种制备这些化合物的方法。这些孕酮衍生物可用作合成1α-位羟基维生素D.sub.3衍生物的中间体。

  公开号：

  US05112998A1

文献信息

• Process for the preparation of pregnane derivatives
  申请人：——

  公开号：US20030181742A1

  公开（公告）日：2003-09-25

  A process for preparing pregnane derivatives represented by the formula (V), 1 which comprises the steps of: reacting an alkali (earth) metal with a compound represented by the formula (I) 2 in the presence of ammonia or an amine, to obtain a compound represented by the formula (II); 3 protecting the hydroxy groups of the obtained compound, to obtain a compound represented by the formula (III); 4 protecting the 3-position carbonyl group of the obtained compound, to obtain a compound represented by the formula (IV); 5 and subjecting the obtained compound to solvolysis; and the compound (II).

  一种制备以公式（V）表示的孕烷衍生物的方法，包括以下步骤：在氨或胺的存在下，将以公式（I）表示的化合物与碱金属（碱土金属）反应，得到以公式（II）表示的化合物；保护所得化合物的羟基，得到以公式（III）表示的化合物；保护所得化合物的3位置羰基基团，得到以公式（IV）表示的化合物；将所得化合物进行溶剂解离反应；以及化合物（II）。
• 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。
• PREGNANE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
  申请人：KURARAY CO., LTD.

  公开号：EP0321572A1

  公开（公告）日：1989-06-28

  Pregnane derivatives represented by general formula (I) (wherein A1 represents a hydrogen atom or a hydroxy group, A2 represents a substituent such as a hydroxy group when A1 represents a hydrogen atom, or A2 represents a hydrogen atom when A1 represents a hydroxy group, or A1 and A2 are combined together to form an oxo group; 01 represents a substituent such as a hydroxy group, and D2 represents a hydrogen atom, or D1 and D2 are combined together to form an epoxy group or a single bond; D3, D5 and D7 each represents a hydrogen atom, D4 represents a hydroxy group, and D6 represents a substituent such as a hydroxy group, or D3 and D4 may be combined together to form an epoxy group or a single bond, or D4 and D5 may be combined together to form a single bond, D5 and D6 may be combined together to form an epoxy group or a single bond, or D6 and D7 may be combined together to form a single bond; and X1 and X2 each represents a lower alkoxy group or, when combined together, they represent a lower alkylenedioxy or oxo group) and a process for their preparation. The pregnane derivatives are useful as intermediates for synthesizing vitamin D3 having a hydroxy group in the 1α-position.

  由通式(I)代表的孕烷衍生物（其中A1代表氢原子或羟基，当A1代表氢原子时A2代表羟基等取代基，或当A1代表羟基时A2代表氢原子，或A1和A2结合在一起形成氧代基；01代表羟基等取代基，D2代表氢原子，或D1和D2结合在一起形成环氧基或单键；D3、D5 和 D7 各自代表氢原子，D4 代表羟基，D6 代表取代基，如羟基，或 D3 和 D4 可结合在一起形成环氧基或单键，或 D4 和 D5 可结合在一起形成单键，D5 和 D6 可结合在一起形成环氧基或单键，或 D6 和 D7 可结合在一起形成单键；X1和X2各自代表一个低级烷氧基，或者当它们结合在一起时，代表一个低级烷二氧基或氧化基团）及其制备方法。孕烷衍生物可作为合成 1α 位具有羟基的维生素 D3 的中间体。
• 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。