1,5,7-cholestatrien-3β-ol | 54604-59-0

• 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: 1,5,7-cholestatrien-3β-ol
• 英文别名: cholesta-1,5,7-trien-3β-ol；Cholesta-1,5,7-trien-3beta-ol；(3R,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-4,9,11,12,14,15,16,17-octahydro-3H-cyclopenta[a]phenanthren-3-ol
• CAS: 54604-59-0
• 化学式: C₂₇H₄₂O
• 分子量: 382.63
• InChiKey: RSUDQJUKBUVQHK-DDPQNLDTSA-N

物化性质

• 沸点：
  504.1±39.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5,7-cholestatrien-3β-ol 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  A new synthetic method of 1β- and 2β-hydroxyprovitamin D3, the precursor of the 1β- and 2β-hydroxyvitamin D3

  摘要：

  A new method was described for the synthesis of 1 beta- and 2 beta-hydroxyprovitamins D-3, the photoprecusors of 1 beta- and 2 beta-hydroxyvitamin D-3. The key step of stereoselective introduction of C-1 and C-2 hydroxy groups was performed with a very mild method for the hydroxybromination of the D-A cyclo adduct with tribromoisocyanuric acid(TBCA)/water. The newly developed method requires no toxic or expensive reagents and 1 beta(2 beta)-hydroxyprovitamin D-3 was obtained with excellent yield and stereoselectivity.

  DOI：

  10.3998/ark.5550190.p009.598
• 作为产物：
  描述：

  (8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-8,9,11,12,14,15,16,17-八氢环戊烯并[a]菲-3-酮 在 sodium tetrahydroborate 、 乙酸异丙烯酯 、 calcium borohydride 、 对甲苯磺酸 、 calcium chloride 作用下， 以 甲醇 、 乙醚 、 乙醇 、 乙酸丁酯 为溶剂， 反应 10.0h， 生成 1,5,7-cholestatrien-3β-ol
  参考文献：
  名称：

  A Convenient Synthesis of Cholesta-1,5,7-trien-3β-ol

  摘要：

  胆固醇-4,6-二烯-3β-醇（4）是通过在催化剂四丁基溴化铵的存在下，用碱对7-溴胆固醇进行脱氢溴化反应而选择性获得的。将4与2,3-二氯-5,6-二氰基-对苯醌氧化，得到胆固醇-1,4,6-三烯-3-酮（7）。在酸性条件下，将7与乙酸异丙烯酯反应，得到3-乙酰氧基-1,3,5,7-胆固醇四烯，用硼氢化钙还原，得到胆固醇-1,5,7-三烯-3β-醇（2）。

  DOI：

  10.1246/bcsj.59.3702

文献信息

• Synthesis of 1.alpha.-hydroxy-7-dehydrosteroids
  申请人：Diamond Shamrock Corp.

  公开号：US04287129A1

  公开（公告）日：1981-09-01

  Enol acetylation is carried out on a variety of 1,4,6-trien-3-ones to form 1,3,5,7 tetraene structures from which 1.alpha.-hydroxy-7-dehydro steroids are obtained. The compounds are intermediates used in the preparation of vitamin D.sub.3 metabolites such as 1.alpha.,25-dihydroxyvitamin D.sub.3 and 1.alpha.-hydroxyvitamin D.sub.3.

  Enol乙酰化是在各种1,4,6-三烯-3-酮上进行的，形成1,3,5,7-四烯结构，从中获得1.alpha.-羟基-7-脱氢类固醇。这些化合物是用于制备维生素D.sub.3代谢物的中间体，如1.alpha.,25-二羟基维生素D.sub.3和1.alpha.-羟基维生素D.sub.3。
• A Convenient Synthesis of Cholesta-1,5,7-trien-3β-ol
  作者：Yoji Tachibana

  DOI：10.1246/bcsj.59.3702

  日期：1986.11

  Cholesta-4,6-dien-3β-ol (4) was obtained selectively by the dehydrobromination of 7-bromocholesterol with a base in the presence of a catalytic amount of tetrabutylammonium bromide. The oxidation of 4 with 2,3-dichloro-5,6-dicyano-p-benzoquinone gave cholesta-1,4,6-trien-3-one (7). Treatment of 7 with isopropenyl acetate under acidic conditions afforded 3-acetoxy-1,3,5,7-cholestatetraene, which was reduced with calcium borohydride to yield cholesta-1,5,7-trien-3β-ol (2).

  胆固醇-4,6-二烯-3β-醇（4）是通过在催化剂四丁基溴化铵的存在下，用碱对7-溴胆固醇进行脱氢溴化反应而选择性获得的。将4与2,3-二氯-5,6-二氰基-对苯醌氧化，得到胆固醇-1,4,6-三烯-3-酮（7）。在酸性条件下，将7与乙酸异丙烯酯反应，得到3-乙酰氧基-1,3,5,7-胆固醇四烯，用硼氢化钙还原，得到胆固醇-1,5,7-三烯-3β-醇（2）。
• Vitamin D3 derivatives having a substituent at 2-position
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0184206A2

  公开（公告）日：1986-06-11

  Ala-hydroxy vitamin D, derivative of the formula: where R, is a hydroxyl group, an amino group or the group: OR' (where R' is a lower alkyl group having 1 to 7 carbon atoms that may or may not be substituted by a hydroxyl group, a halogen atom, a cyano group, a lower alkoxy group having 1 to 3 carbon atoms, an amino group, or an acylamino group); R2 is a hydrogen atom or a hydroxyl group), and a process for preparing the same are disclosed. The compounds represented by the formula above are effective for calcium control and for induction of differentiation in tumor cells and, therefore, are useful as antitumor agents and a medicine for treating calcium dysbolism-caused diseases.

  本发明公开了阿拉羟基维生素D的衍生物的化学式，其中R是一个羟基，一个氨基或者一个基团：OR'（其中R'是一个有1到7个碳原子的低级烷基基团，可以或不可以被一个羟基，卤素原子，氰基，一个有1到3个碳原子的低级烷氧基基团，一个氨基或者一个酰胺基取代）；R2是一个氢原子或者一个羟基。本发明还公开了制备该化合物的方法。上述化学式所代表的化合物在钙控制和肿瘤细胞分化诱导方面具有有效性，因此，它们可以作为抗肿瘤剂和治疗钙代谢失调疾病的药物。
• 1,3,5,7-Tetradehydro steroids, their preparation and their use in the synthesis of 1-alpha-hydroxy-7 dehydro steroids
  申请人：DIAMOND SHAMROCK CORPORATION

  公开号：EP0045884A1

  公开（公告）日：1982-02-17

  The carrying out of enol acetylation on a variety of 1,4,6-trien-3-ones to form 1,3,5,7 tetraene of the formula in which R is selected from the group consisting of C8H16OH; C8H16O2CCH3, C8H16O2C and C5H8O2CH3 and in which R'CO- is the residue of an acylating agent. From these compounds 1-alpha-hydroxy-7-dehydro-steroids are obtained. The compounds are intermediates used in the preparation of vitamin D3 metabolites such as 1-delta-25-dihydroxyvitamin D3 and 1-delta-hydroxyvitamin D3.

  对各种 1,4,6-三烯-3-酮进行烯醇乙酰化反应，生成式中的 1,3,5,7-四烯。 其中 R 选自 C8H16OH、C8H16O2CCH3、C8H16O2C 和 C5H8O2CH3 所组成的组，其中 R'CO- 是酰化剂的残留物。从这些化合物中可以得到 1-α-羟基-7-脱氢类固醇。 这些化合物是用于制备维生素 D3 代谢物（如 1-δ-25-二羟基维生素 D3 和 1-δ-羟基维生素 D3）的中间体。
• BIOLOGICAL PROCESS FOR PREPARING 25-HYDROXYLATED STEROIDS
  申请人：MERCIAN CORPORATION

  公开号：EP0916736A1

  公开（公告）日：1999-05-19

  A biological process for producing steroids hydroxylated at the 25-position thereof comprises adding steroids (excluding cholesterol) to the cells or culture liquid of a microorganism of the genus Amycolata or Sphingomonas capable of hydroxylating the steroids at the 25-position thereof to convert a hydrogen atom bonded to a carbon atom at the 25-position of each steroid into hydroxyl group. By this process, steroids(other than cholesterol) can be biologically hydroxylated at the 25-position by using microorganisms other than those of the genus Streptomyces.

  一种生产在 25 位羟基化的类固醇的生物工艺包括将类固醇（不包括胆固醇）加入到能够在 25 位羟基化类固醇的 Amycolata 或 Sphingomonas 属微生物的细胞或培养液中，将每个类固醇 25 位上与碳原子结合的氢原子转化为羟基。通过这一过程，可以利用链霉菌属以外的微生物在 25 位对类固醇（胆固醇除外）进行生物羟基化。