5α（H）-Cholestan-3α醇 | 516-95-0

• 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
• 中文名称: 5α（H）-Cholestan-3α醇
• 英文名称: epicholestanol
• 英文别名: epidihydrocholesterol；3α,5α-dihydro-3-cholesterol；5α-cholestan-3-α-ol；5α-cholestan-3α-ol；3α-hydroxycholestane；Epidihydrocholesterin；(3R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 516-95-0
• 化学式: C₂₇H₄₈O
• 分子量: 388.678
• InChiKey: QYIXCDOBOSTCEI-FBVYSKEZSA-N

物化性质

• 熔点：
  185-186°
• 比旋光度：
  D20 +34° (c = 1.7 in chloroform)
• 沸点：
  454.32°C (rough estimate)
• 密度：
  0.9506 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  5α（H）-Cholestan-3α醇 在 碘甲烷 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以94%的产率得到3β-Iodocholestane
  参考文献：
  名称：

  有机官能团的设计和反应性：高度结晶的2-烷氧基N，N'-二苯基-1,3,2-二氮杂膦酸酯及其易于转化为卤代烷的方法

  摘要：

  醇作为2-烷氧基N，N'-二苯基-1,3,2-二氮杂磷杂环戊烷的官能化提供了用于表征目的的高度结晶的衍生物。这些三价磷衍生物容易进行且温和地转化为相应的卤代烷，且具有构型反转。

  DOI：

  10.1016/s0040-4039(00)85615-4
• 作为产物：
  描述：

  4-胆甾烯-3-酮 在 正戊醚 、 aluminum isopropoxide 、 异丙醇 、 铂 作用下， 生成 5α（H）-Cholestan-3α醇
  参考文献：
  名称：

  Elliptic Curves and Class Fields of Real Quadratic Fields: Algorithms and Evidence

  摘要：

  The article [Darmon 02] proposes a conjectural p-adic analytic construction of points on (modular) elliptic curves, points which are defined over ring class fields of real quadratic fields. These points are related to classical Heegner points in the same way as Stark units to circular or elliptic units.' For this reason they are called "Stark-Heegner points," following a terminology introduced in [Darmon 98].If K is a real quadratic field, the Stark-Heegner points attached to K are conjectured to satisfy an analogue of the Shimura reciprocity law, so that they can in principle be used to find explicit generators for the ring class fields of K. It is also expected that their heights can be expressed in terms of derivatives of the Rankin L-series attached to E and K, in analogy with the Gross-Zagier formula.The main goal of this paper is to describe algorithms for calculating Stark-Heegner points and supply numerical evidence for the Shimura reciprocity and Gross-Zagier conjectures, focussing primarily on elliptic curves of prime conductor.

  DOI：

  10.1080/10586458.2002.10504467

文献信息

• Cu-catalyzed coupling of indanone oxime acetates with thiols to 2,3-difunctionalized indenones
  作者：Yuanyuan Fu、Xueyan Zhao、Dengfeng Chen、Jinyue Luo、Shenlin Huang

  DOI：10.1039/d1cc04167c

  日期：——

  A Cu-catalyzed coupling reaction of indanone oxime acetates with thiols has been developed for the synthesis of 2,3-functionalized 1-indenones. This protocol has several features including easy mild reaction conditions, stabilized enamine products, good tolerance of functional groups, and no external oxidants. This reaction enables direct derivatization on the indanone ring to provide valuable functionalized

  茚满酮肟乙酸酯与硫醇的 Cu 催化偶联反应已被开发用于合成 2,3-功能化 1-茚酮。该协议有几个特点，包括容易温和的反应条件、稳定的烯胺产品、良好的官能团耐受性和无外部氧化剂。该反应能够在茚满酮环上直接衍生化，从而在室温下提供有价值的官能化茚酮。
• Mitsunobu reactions with methanesulfonic acid; The replacement of equatorial hydroxyl groups by azide with net retention of configuration
  作者：Anthony P. Davis、Stephan Dresen、Laurence J. Lawless

  DOI：10.1016/s0040-4039(97)00886-1

  日期：1997.6

  of equatorial cyclohexanols with Ph3P/DEAD/MsOH gives clean conversion to the axial mesylates. Subsequent reaction with NaN3 gives the equatorial azides in overall yields of 74–87%. Axial hydroxyl groups are not affected, allowing the regioselective conversion of methyl cholate into a 3α-azidodiol intermediate for steroid-based synthetic receptors.

  用Ph 3 P / DEAD / MsOH处理赤道环己醇可将其干净地转化为轴向甲磺酸酯。随后与NaN 3的反应使赤道叠氮化物的总产率为74-87％。轴向羟基不受影响，允许胆甾醇将区域选择性地转化为基于类固醇的合成受体的3α-叠氮二醇中间体。
• Sulfuric Acid Adsorbed on Silica Gel. A Multipurpose Acid Catalyst
  作者：Flavio Chávez、Silvia Suárez、Miguel A. Díaz

  DOI：10.1080/00397919408019058

  日期：1994.8

  ketones to 1,3-dioxolanes and their hydrolysis, α,β-unsaturated ketones to enol ethers, and alcohols to methyl-methoxyethyl ethers are performed efficiently in high yield with sulfuric acid adsorbed on silica gel as catalyst.

  摘要 醇类脱水、酮类转化为 1,3-二氧戊环及其水解、α,β-不饱和酮类转化为烯醇醚、醇类转化为甲氧基乙基醚等一系列酸催化反应均能以高收率高效进行。硫酸吸附在硅胶上作为催化剂。
• A Simple and Efficient Catalytic Method for the Reduction of Ketones
  作者：Jesper Ekström、Jenny Wettergren、Hans Adolfsson

  DOI：10.1002/adsc.200700091

  日期：2007.7.2

  A range of ketones was efficiently reduced in the presence of catalytic amounts of lithium isopropoxide in 2-propanol under microwave heating, with alcohol products being formed in yields up to 99 %.

  在微波加热下，在2-丙醇中催化量的异丙醇锂存在下，有效地还原了一系列酮，形成的醇产物的收率最高为99％。
• Nicotinoyl Azide (NCA)-Mediated Mitsunobu Reaction: An Expedient One-Pot Transformation of Alcohols into Azides
  作者：Gianluca Papeo、Helena Posteri、Paola Vianello、Mario Varasi

  DOI：10.1055/s-2004-831254

  日期：——

  A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.

  描述了一种实用而简便的方法，允许从醇类制备叠氮化合物。该过程涉及氧膦型活化，并基于使用烟酰叠氮（NCA），这是一种廉价且易于获得的叠氮离子源。

表征谱图