1α, 3β, 24-trihydroxycholest-5-ene | 59780-19-7

• 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: 1α, 3β, 24-trihydroxycholest-5-ene
• 英文别名: 1α,3β,24-trihydroxycholest-5-ene；1α,24-dihydroxycholesterol；1α,3β,24χ-Trihydroxycholest-5-en；1alpha,24-Dihydroxycholesterol；(1S,3R,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol
• CAS: 59780-19-7
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: CXRFZFYBGWQFGK-IEFHHKAWSA-N

物化性质

• 沸点：
  547.1±35.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1α, 3β, 24-trihydroxycholest-5-ene 在 吡啶 作用下， 生成 1α,3β,24(R)-trihydroxycholesta-5,7-diene
  参考文献：
  名称：

  Morisaki,M. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1421 - 1424

  摘要：

  DOI：
• 作为产物：
  描述：

  1α, 2α-epoxy-24-keto-cholesta-4,6-dien-3-one 在 ammonium chloride 作用下， 以 四氢呋喃 、 二氧化碳 、 丙酮 为溶剂， 以68%的产率得到1α, 3β, 24-trihydroxycholest-5-ene
  参考文献：
  名称：

  Novel 1.alpha.,24-dihydroxycholecalciferol compositions, novel

  摘要：

  1.alpha., 24-二羟基胆钙化醇及其衍生物，对于由肝功能衰竭、肾功能衰竭、胃肠道功能衰竭和甲状旁腺功能衰竭引起的钙磷代谢异常以及相关骨病的治疗具有减少副作用的作用。制备这种新型1.alpha., 24-二羟基胆钙化醇及其衍生物的方法是从通过在液氨或液胺存在下，将1.alpha., 2.alpha.-环氧-24-酮基-胆甾-4,6-二烯-3-酮与碱金属和质子给体反应制备的1.alpha., 24-二羟基胆固醇开始。将1.alpha., 24-二羟基胆固醇与烯丙基溴化剂反应，然后与脱溴化剂接触，得到1.alpha.,3.beta., 24-三羟基胆甾-5,7-二烯衍生物，然后可以通过在有机溶剂中紫外辐射，随后异构化，将其转化为1.alpha., 24-二羟基胆钙化醇。还提供了将1.alpha., 24-二羟基胆固醇分离成(S)-对映体和(R)-对映体的方法，以及将1.alpha., 3.beta., 24(S)-和1.alpha., 3.beta., 24(R)-三羟基胆甾-5,7-二烯中的至少一种与三羟基胆甾-4,6-二烯分离的方法。

  公开号：

  US04022891A1

文献信息

• Process for production of 1-.alpha., 3-.beta., 24-trihydroxy .DELTA.-.sup.5
  申请人：Teijin Limited

  公开号：US05117015A1

  公开（公告）日：1992-05-26

  A process for producing a 1.alpha.,3.beta.,24-trihydroxy-.DELTA..sup.5 -steroid represented by the formula (II): ##STR1## wherein R.sub.1 and R.sub.2, independently, represent a hyrogen atom, or R.sub.1 and R.sub.2 together form a single bond, R.sub.3 represents an unsubstituted or halogen-substituted lower alkyl, and R.sub.4 represents a hydrogen atom, hydroxy or a protected hydroxy, comprising reducing a 1.alpha.,2.alpha.-epoxy-.DELTA..sup.4,6 -3,24-dioxosteroid represented by the formula (I) ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the same meanings as defined in formula (II), using an alkaline metal or alkaline earth metal and a proton donor in a solvent comprising ammonia or amine characterized in that at an early stage of the reaction, the 1.alpha.,2.alpha.-epoxy-.DELTA..sup.4,6 -3,24-dioxosteroid is reacted with the alkaline metal or alkaline earth metal in the presence of a proton acceptor, and then at a later stage of the reaction, a resulting intermediate product is reacted with the proton donor.

  生产1α,3β,24-三羟基-Δ5-类固醇的方法，该类固醇由以下结构式（II）表示：其中R.sub.1和R.sub.2分别代表氢原子，或者R.sub.1和R.sub.2一起形成一个单键，R.sub.3代表未取代或卤素取代的低碳链基，R.sub.4代表氢原子、羟基或保护羟基，包括将由以下结构式（I）表示的1α,2α-环氧-Δ4,6-3,24-二氧类固醇还原为1α,3β,24-三羟基-Δ5-类固醇，其中R.sub.1、R.sub.2、R.sub.3和R.sub.4的含义与结构式（II）中定义的含义相同，使用含有氨或胺的溶剂中的碱金属或碱土金属和质子给体，其特征在于在反应的早期阶段，1α,2α-环氧-Δ4,6-3,24-二氧类固醇在质子受体的存在下与碱金属或碱土金属发生反应，然后在反应的后期阶段，将得到的中间产物与质子给体发生反应。
• Meiosis regulating compounds
  申请人：——

  公开号：US20010005757A1

  公开（公告）日：2001-06-28

  Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula 1 wherein the substituents are as defined in the specification.

  某些化合物在结构上与可以从公牛睾丸和人类卵泡液中提取的天然化合物相关，可用于调节卵母细胞和男性生殖细胞中的减数分裂。其中一些化合物对治疗不孕症有用，而其他化合物则可用作避孕药。这些化合物具有结构式，其中取代基如规范中定义。
• Process for producing steroid compounds having an oxogroup in the side chain
  申请人：TEIJIN LIMITED

  公开号：EP0013082A1

  公开（公告）日：1980-07-09

  A process for producing a steroid compound having an oxo group in the side chain, which comprises condensing an acid halide having a steroid skeleton with an organozinc compound at a halocarbonyl group of the acid halide in an inert organic medium in the presence of a catalytic amound of an ether capable of forming a complex with the organozinc compound and, if desired, hydrolyzing the product. The process gives the steroid compound in a high yield, and often in an almost quantitative yield. The steroid compound can be an important intermediate for the production of vitamin D3 analogs, such as active forms of vitamin D3.

  一种生产侧链中含有氧代基团的甾体化合物的工艺，包括在惰性有机介质中，在能与有机锌化合物形成络合物的醚的催化下，在酸卤化物的卤代羰基上将具有甾体骨架的酸卤化物与有机锌化合物缩合，并在需要时水解产物。该工艺可以得到高产率的甾体化合物，通常几乎可以达到定量产率。类固醇化合物可以作为生产维生素 D3 类似物（如活性维生素 D3）的重要中间体。
• Asymmetric isopropylation of steroidal 24-aldehydes for the synthesis of 24(R)-hydroxycholesterol
  作者：Makoto Okamoto、Masayasu Tabe、Takao Fujii、Toshio Tanaka

  DOI：10.1016/0957-4166(95)00073-x

  日期：1995.3

  The chiral beta-amino alcohols-catalyzed addition of diisopropylzinc to steroidal 24-aldehydes successfully provided 24(R)-hydroxycholesterols in good yields with high diastereoselectivities, which are synthetic intermediates of 1 alpha,24(R)-dihydroxyvitamin D-3 (1). alpha,beta-Unsaturated steroidal aldehydes were found to give the corresponding isopropylated adducts in much higher yields (up to 91%) than those of saturated steroidal aldehydes.
• Process for production of 1alfa, 3beta, 24-trihydroxy-delta5-steroids
  申请人：TEIJIN LIMITED

  公开号：EP0349869B1

  公开（公告）日：1995-08-30