lanost-8-en-3-one | 1255-26-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: lanost-8-en-3-one
• 英文别名: 5α-lanost-8-en-3-one；lanosta-8,24-dien-3-one；Lanost-8-en-3-on；Lanosten-(8)-on-(3)；5α-Lanost-8-en-3-on；Lanost-8(9)-en-3-on；(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 1255-26-1
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: JVYYINJWLIGZGB-WUELKCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  lanost-8-en-3-one 在 盐酸 、 selenium(IV) oxide 、 amalgamated zinc 、 溶剂黄146 作用下， 生成 lanosta-7,9(11)-diene
  参考文献：
  名称：

  279.羊毛甾醇。第四部分 由脱水剂作用形成的烃

  摘要：

  DOI：

  10.1039/jr9470001467
• 作为产物：
  描述：

  羊毛甾醇 在 palladium on activated charcoal 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯酚 为溶剂， 反应 3.0h， 生成 lanost-8-en-3-one
  参考文献：
  名称：

  Iridium-Catalyzed Intermolecular Amidation of sp³ C–H Bonds: Late-Stage Functionalization of an Unactivated Methyl Group

  摘要：

  Reported herein is the iridium-catalyzed direct amidation of unactivated sp(3) C-H bonds. With sulfonyl and acyl azides as the amino source, the amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C-H functionalization.

  DOI：

  10.1021/ja501014b

文献信息

• Reaction of 5α, and 5β,3-keto-steroids with potassium superoxide
  作者：E. Alvarez、C. Betancor、R. Freire、A. Martin、E. Suárez

  DOI：10.1016/s0040-4039(01)82949-x

  日期：1981.1

  A regiospecific behaviour is observed in the reaction of 5α and 5β-keto-steroids with potassium superoxide; so the 5α- cholestan-3-one (I) gave the lactol II and the 3-keto-smilagenin (VII) gave the keto-acid VIIIa and a small amount of the diacid IXa. The 3-keto-dihydrolanosterol (V) afforded the lactol VI.

  在5α和5β-酮类固醇与过氧化钾的反应中观察到了区域特异性行为。因此5α-胆甾醇-3-酮（I）生成了乳糖醇II，3-酮基-丝氨酸生成素（VII）生成了酮酸VIIIa和少量的二酸IXa。3-酮-二氢羊毛甾醇（V）提供了乳糖醇VI。
• Some applications of nickel boride as a desulphurising agent. An improved route to triterpene 2-enes
  作者：Robin B. Boar、David W. Hawkins、James F. McGhie、Derek H. R. Barton

  DOI：10.1039/p19730000654

  日期：——

  defined for the desulphurisation of ethylene dithioacetals with nickel boride. Normally a mixture of saturated and unsaturated products is formed. Nickel boride is inferior to Raney nickel for the desulphurisation of thiophens. Hemithioacetals are rapidly cleaved by nickel boride, allowing regeneration of the ketone. Triterpene 2-enes are obtained in excellent yield from 3-ketones by desulphurisation

  定义了将乙二硫缩醛与硼化镍进行脱硫的最佳条件。通常形成饱和和不饱和产物的混合物。硼化镍比阮内镍劣于噻吩脱硫。半硫缩醛可被硼化镍快速裂解，从而使酮再生。通过用硼化镍或阮内镍对中间苄基硫代（烯醇醚）进行脱硫，可以从3-酮以优异的收率得到三萜2烯。
• Revision and Confirmation of the Regiochemistry of Isoxazoles Derived from Methyl Oleanonate and Lanost-8-en-3-one. Synthesis of a New Lanostane Triterpenoid with a Cyano-enone Functionality in Ring A
  作者：Yukiko Honda、Tadashi Honda、Sujata Roy、Gordon W. Gribble

  DOI：10.1021/jo034056y

  日期：2003.6.1

  lanost-8-en-3-one (10) give predominantly [3,2-c]isoxazoles. On the contrary, we have confirmed that both compounds 5 and 10 do not give [3,2-c]isoxazoles but rather afford regioselectively [2,3-d]isoxazoles in good yields. Consequently, a new lanostane triterpenoid with a cyano-enone functionality in ring A was synthesized in two steps from the corresponding [2,3-d]isoxazole, which is interesting from the perspective

  以前有报道说，油酸甲酯（5）和羊毛脂8-烯-3-酮（10）主要产生[3,2-c]异恶唑。相反，我们已经证实化合物5和10都不产生[3,2-c]异恶唑，而是以高收率选择性地提供区域选择性的[2,3-d]异恶唑。因此，从相应的[2,3-d]异恶唑分两步合成了新的环A中具有氰基-烯酮官能团的羊毛甾烷三萜，这从生物学活性的角度来看是有趣的，因为羊毛甾醇是类固醇的生物遗传前体。
• Effects of oxygenated lanosterol analogs on cholesterol biosynthesis from lanosterol.
  作者：YOSHIKO SONODA、YOSHIHIRO SATO

  DOI：10.1248/cpb.31.1698

  日期：——

  The effects of oxygenated lanosterol derivatives (1-14) on cholesterol biosynthesis from [24-3H]-lanosterol were tested in 10000×g supernatant (S10) fraction of rat liver homogenate (RLH). Among the derivatives studied, 7-oxo-24, 25-dihydrolanosterol (11) was most active in depressing cholesterol biosynthesis from lanosterol. The inhibitory activities of these derivatives on cholesterol synthesis are discussed in relation to the position and stereochemistry of the oxygen group on the side chain and the sterol nucleus.

  研究人员在大鼠肝匀浆（RLH）10000×g 上清液（S10）中测试了含氧羊毛甾醇衍生物（1-14）对[24-3H]-羊毛甾醇胆固醇生物合成的影响。在所研究的衍生物中，7-氧代-24，25-二氢羊毛甾醇（11）在抑制由羊毛甾醇产生的胆固醇生物合成方面活性最强。本文讨论了这些衍生物对胆固醇合成的抑制作用与侧链上氧基团的位置和立体化学以及甾醇核的关系。
• STEREOCHEMISTRY OF REDUCTION OF KETONES BY COMPLEX METAL HYDRIDES
  作者：Owen H. Wheeler、José L. Mateos

  DOI：10.1139/v58-210

  日期：1958.10.1

  The stereochemistry of the reduction of a number of cyclic ketones with complex metal hydrides has been determined. In the absence of any large steric effect in the ketones, the reduction is essentially stereospecific, giving the more stable alcohol.

  已经确定了用络合金属氢化物还原许多环酮的立体化学。在酮中不存在任何大的空间效应的情况下，还原基本上是立体定向的，从而得到更稳定的醇。