20-methyl-pregna-5,20-dien-3β-ol | 17879-91-3

• 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: 20-methyl-pregna-5,20-dien-3β-ol
• 英文别名: (3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-(prop-1-en-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol；20-Methylpregna-5,20-dien-3beta-ol；(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-prop-1-en-2-yl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 17879-91-3
• 化学式: C₂₂H₃₄O
• 分子量: 314.511
• InChiKey: JRWLCFVPJFFOTJ-BIBIXIOVSA-N

物化性质

• 熔点：
  133-134 °C(Solv: methanol (67-56-1))
• 沸点：
  421.5±44.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  20-methyl-pregna-5,20-dien-3β-ol 在 吡啶 、 hydroxylamine-O-sulfonic acid 作用下， 反应 3.0h， 生成 22-amino-5-pregnen-3β-yl laurate
  参考文献：
  名称：

  Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia

  摘要：

  For monitoring low-density lipoprotein receptors (LDLr) in tumors and in livers of patients with familial hypercholesterolemia (FH) treated with gene therapy, a series of tricarbocyanine cholesteryl laurates were synthesized with the cholesteryl laurate moiety serving as the lipid-chelating anchor for low-density lipoprotein (LDL). One of these conjugates, TCL17, was successfully used to label LDL to give a new NIRF, TCL17-LDL. Ex vivo biological studies on an LDLr overexpressing tumor model, human hepatoblastoma G(2) (HepG(2)), confirmed that this NIRF were internalized selectively by the tumor and detected with high sensitivity by a low-temperature 3-D redox scanner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00193-2
• 作为产物：
  描述：

  孕烯醇酮 在 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 甲醇 、 叔丁醇 为溶剂， 生成 20-methyl-pregna-5,20-dien-3β-ol
  参考文献：
  名称：

  Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia

  摘要：

  For monitoring low-density lipoprotein receptors (LDLr) in tumors and in livers of patients with familial hypercholesterolemia (FH) treated with gene therapy, a series of tricarbocyanine cholesteryl laurates were synthesized with the cholesteryl laurate moiety serving as the lipid-chelating anchor for low-density lipoprotein (LDL). One of these conjugates, TCL17, was successfully used to label LDL to give a new NIRF, TCL17-LDL. Ex vivo biological studies on an LDLr overexpressing tumor model, human hepatoblastoma G(2) (HepG(2)), confirmed that this NIRF were internalized selectively by the tumor and detected with high sensitivity by a low-temperature 3-D redox scanner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00193-2

文献信息

• [EN] C7 SUBSTITUTED OXYSTEROLS AND METHODS AS NMDA MODULATORS<br/>[FR] OXYSTÉROLS SUBSTITUÉS EN C7 ET PROCÉDÉS EN TANT QUE MODULATEURS NMDA
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2018064649A1

  公开（公告）日：2018-04-05

  Compounds are provided according to Formula (A): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1A, R1B, n, R2A, R2B, R3, and R4 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

  根据公式(A)提供化合物：以及药用可接受的盐和药物组合物；其中R1A，R1B，n，R2A，R2B，R3和R4如本文所述定义。本发明的化合物被认为可用于预防治疗各种疾病。
• [EN] OXYSTEROLS AND METHODS OF USE THEREOF<br/>[FR] OXYSTÉROLS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2018075698A1

  公开（公告）日：2018-04-26

  Compounds are provided according to Formula (A): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, R4, R5, R6, and RG are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

  根据公式(A)提供化合物：以及药用可接受的盐和药物组合物；其中R1、R2、R3、R4、R5、R6和RG如本文所述定义。本发明的化合物被认为对预防和治疗多种疾病有用。
• Synthesis of Trisubstituted Alkenyl Boronic Esters from Alkenes Using the Boryl-Heck Reaction
  作者：William B. Reid、Donald A. Watson

  DOI：10.1021/acs.orglett.8b02949

  日期：2018.11.2

  The direct borylation of disubstituted alkenes is reported. These conditions allow for the conversion of a variety 1,1- and 1,2-disubstituted alkenes to trisubstituted alkenyl boronic esters with outstanding yields and excellent E/Z selectivities. The utility of this reaction has been demonstrated with several downstream functionalization reactions, which allow access to diverse, stereodefined, functionalized

  报道了二取代烯烃的直接硼基化。这些条件允许将各种 1,1-和 1,2-二取代烯烃转化为三取代烯基硼酸酯，具有出色的产率和优异的E / Z选择性。该反应的实用性已通过几个下游官能化反应得到证明，这些反应允许获得多种立体定义的官能化烯烃。机理研究与硼基-赫克途径一致。
• [EN] OXYSTEROLS AND METHODS OF USE THEREOF<br/>[FR] OXYSTÉROLS ET LEURS MÉTHODES D'UTILISATION
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2017173358A1

  公开（公告）日：2017-10-05

  Compounds are provided according to Formula (I), and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein A, R1, and R5 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

  根据公式（I）提供化合物及其药用可接受的盐和药物组成；其中A、R1和R5如本文所定义。本发明的化合物被认为对预防和治疗各种疾病条件有用。
• Geminal dimetallic compounds
  作者：F. Bertini、P. Grasselli、G. Zubiani、G. Cainelli

  DOI：10.1016/s0040-4020(01)92998-9

  日期：1970.1

  The reaction of 1,1-dihalo-alkanes with magnesium and magnesium amalgam has been studied. Methylene bromide and iodide yield, under suitable conditions, a stable solution of methylene magnesium halide which easily olefinates aldehydes and ketones affording the corresponding methylenic olefins in good yields. Other alkylidene halides, under the conditions studied, do not give any stable geminal dimagnesium

  已经研究了1，1-二卤代烷烃与镁和镁汞齐的反应。在合适的条件下，溴甲烷和碘化物的亚甲基卤化物的稳定溶液可以很容易地使醛和酮烯化，从而以高收率得到相应的亚甲基烯烃。尽管在亚烷基卤化物，羰基化合物和镁汞齐之间的原位反应过程中可能存在双晶种，但在研究的条件下，其他亚烷基卤化物不会产生任何稳定的双结晶二铵化合物。提出了考虑到大多数这种已知反应的一般羰基烯烃化方案。