5-Cholesten-1α,3α-diol | 50392-20-6

• 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: 5-Cholesten-1α,3α-diol
• 英文别名: 1α,3α-Dihydroxycholest-5-en；Cholest-5-en-1α,3α-diol；(1S,3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol
• CAS: 50392-20-6
• 化学式: C₂₇H₄₆O₂
• 分子量: 402.661
• InChiKey: UXFVRWPSABSGRQ-SIKHBXEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  29
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1alpha,3beta)-胆甾-5-烯-1,3-二醇 生成 5-Cholesten-1α,3α-diol
  参考文献：
  名称：

  维生素D（钙化醇）及其类似物的研究。13.3-脱氧-3α-甲基-1α-羟基维生素D3、3-脱氧-3α-甲基-1α，25-二羟基维生素D3和1α-羟基-3-表维生素D3。具有构型偏向环的类似物。

  摘要：

  DOI：

  10.1021/jo00398a011

文献信息

• Eine ergiebige Herstellung von 1α,3β-Dihydroxy-Δ⁵-steroiden durch Reduktion von 1α,2α-Epoxy-4,6-dien-3-onen mit Lithium in Ammoniak
  作者：Andor Fürst、Ludvik Labler、Werner Meier

  DOI：10.1002/hlca.19810640621

  日期：1981.9.23

  An Efficient Procedure for Preparing 1α,3β-Dihydroxy-Δ5-steroids by Reduction of 1α,2α-Epoxy-4,6-dien-3-ones with Lithium in Ammonia

  用于制备1α，3β二羟基Δ的有效程序5个由1α还原，-steroids2α环氧-4,6-二烯-3-酮与锂在氨
• Synthesis of active forms of vitamin D. X. Synthesis of 1.ALPHA.-hydroxyvitamin D3.
  作者：MASUO MORISAKI、AKISUKE SAIKA、KIYOSHI BANNAI、MASAKO SAWAMURA、NOBUO IKEKAWA、RUBIOLIGHTBOURN JULIETA

  DOI：10.1248/cpb.23.3272

  日期：——

  1α-Hydroxyvitamin D3 (20) was prepared from cholesterol (1) in ca. 1% overall yield. Hydroboration of the tetrahydropyranyl ether 2 followed by chromic acid oxidation and NaBH4 reduction gave the 6β-ol 5. Brief treatment of its acetate 6 with acid followed by Jones oxidation gave the 6β-acetoxy-3-one (7) in 55% yield from 1. Introduction of C-1 double bond (64%) was effected by bromination of 7, followed by dehydrobromination with CaCO3, yielding the 3-oxo-1-ene 9. Oxidation of 9 with alkaline H2O2 afforded the 1α, 2α-epoxide 10 (80%) and this was converted by successive 6 steps sequences to 1α-hydroxycholesterol 15 in 43% yield. The 5, 7-diene 19 was obtained from the acetate 16 in 40% yield by allylic bromination with N-bromosuccinimide, dehydrobromination with trimethyl phosphite and saponification. Ultraviolet irradiation of 19 in benzene solution followed by thermal isomerization, produced 1α-hydroxyvitamin D3 (20) (20%).

  1α-Hydroxyvitamin D3（20）由胆固醇（1）制备而成，总收率约为 1%。将四氢吡喃基醚 2 加氢硼化，然后进行铬酸氧化和 NaBH4 还原，得到 6β-ol 5。通过对 7 进行溴化，然后用 CaCO3 进行脱氢溴化，得到 3-氧代-1-烯 9，从而引入 C-1 双键（64%）。用碱性 H2O2 氧化 9 得到 1α，2α-环氧化物 10（80%），然后通过连续的 6 个步骤将其转化为 1α-羟基胆固醇 15，收率为 43%。通过 N-溴代丁二酰亚胺的烯丙基溴化反应、亚磷酸三甲酯的脱氢溴化反应和皂化反应，从醋酸酯 16 中得到 5，7-二烯 19，收率为 40%。在苯溶液中对 19 进行紫外线照射，然后进行热异构化反应，可生成 1α- 羟基维生素 D3 (20)（20%）。
• Studies on 1.ALPHA.-hydroxyl derivatives of vitamin D3. I. Syntheses of 1.ALPHA.-hydroxyvitamin D3 and 1.ALPHA.,25-dihydroxyvitamin D3.
  作者：TADASHI SATO、HIROSHI YAMAUCHI、YOSHITAKE OGATA、MASAHIKO TSUJII、TOSHINOBU KUNII、KENGO KAGEI、SHOJI TOYOSHIMA、TADASHI KOBAYASHI

  DOI：10.1248/cpb.26.2933

  日期：——

  1α-Hydroxyvitamin D3 (XIVa) was synthesized from cholesterol (Ia) in ca. 1.5% overall yield. 1α, 2α-Epoxycholest-4-en-3-one (IVa) readily obtained from Ia was converted to 1α, 2α-epoxycholest-5-en-3-one (Va) by the modified deconjugation reaction with t-BuOK in DMSO. Reduction of Va with Ca (BH4)2 and then with LiAlH4 gave 1α-hydroxycholesterol (VIIIa) in 15.6% yield from Ia. Allylic bromination and subsequent dehydrobromination of the diacetate of VIIIa afforded 1α, 3β-diacetoxycholesta-5, 7-diene (XIa), whose saponification gave the corresponding diol (XIIa). 1α-Hydroxyprovitamin D3 (XIIa) in ethanol was irradiated with the ultraviolet lights in the range between 275 and 310 nm through a newly found filter solution. The formed 1α-hydroxyprevitamin D3 (XIIIa) was thermally isomerized into 1α-hydroxyvitamin D3. The yield of XIVa from XIIa was ca. 25%. These procedures were applied to 25-hydroxycholesterol (Ib) and 1α, 25-dihydroxyvitamin D3 (XIVb) was obtained ca. 0.4% overall yield from Ib.

  1α-羟基维生素 D3（XIVa）由胆固醇（Ia）合成，总收率约为 1.5%。1α，2α-环氧胆甾烷-4-烯-3-酮（IVa）很容易从 Ia 中获得，通过在 DMSO 中与 t-BuOK 的改进脱钩反应转化为 1α，2α-环氧胆甾烷-5-烯-3-酮（Va）。用 Ca (BH4)2 还原 Va，然后用 LiAlH4 还原，从 Ia 得到 1α-hydroxycholesterol (VIIIa)，收率为 15.6%。对 VIIIa 的二乙酸酯进行烯丙基溴化和随后的脱氢溴化，可得到 1α，3β-二乙酰氧基胆甾烷-5，7-二烯（XIa），对其进行皂化可得到相应的二醇（XIIa）。乙醇中的 1α-羟基维生素 D3（XIIa）通过新发现的滤液，在 275 至 310 纳米范围内接受紫外线照射。生成的 1α-羟基维生素 D3（XIIIa）经热异构化为 1α-羟基维生素 D3。从 XIIa 生成 XIVa 的产率约为 25%。将这些步骤应用于 25-羟基胆固醇（Ib），从 Ib 中得到 1α，25-二羟基维生素 D3（XIVb），总产率约为 0.4%。
• 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。
• US6486145B2
  申请人：——

  公开号：US6486145B2

  公开（公告）日：2002-11-26