(3aR,4S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-dione | 113726-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-dione
• 英文别名: (3aR,4S,7aS)-4-bromooctahydro-7a-methyl-1H-indene-1,5-dione；(3aR,4S,7aS)-4-Bromo-7a-methylhexahydroindan-1,5-dione；(3aR,4S,7aS)-4-bromo-7a-methylperhydroindene-1,5-dione；(3aR,4S,7aS)-4-bromo-7a-methylhexahydro-1H-indene-1,5(4H)-dione；(3aR,4S,7aS)-4-bromo-7a-methyl-2,3,3a,4,6,7-hexahydroindene-1,5-dione
• CAS: 113726-26-4
• 化学式: C₁₀H₁₃BrO₂
• 分子量: 245.116
• InChiKey: LYXZMWUBUGPEMB-JUWDTYFHSA-N

物化性质

• 熔点：
  133-154 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  324.5±42.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aR,4S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-dione 在 2,6-二甲基吡啶 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (Z)-des-A,B-8β-[(tert-butyldimethylsilyl)oxy]pregn-17(20)-ene
  参考文献：
  名称：

  Synthesis of Denosomin–Vitamin D₃ Hybrids and Evaluation of Their Anti-Alzheimer’s Disease Activities

  摘要：

  As an extension of previously conducted studies on developing an anti-Alzheimer's disease agent, denosomin (1-deoxy-24-norsominone, an artificial inducer of neurite elongation), derivatives were designed and synthesized based on the hypothesis that our denosomin would exhibit axonal extension activity via a 1,25D(3)-membrane-associated, rapid response steroid-binding protein (1,25D(3)-MARRS) pathway. The biological assay revealed that the hybridization of characteristic delta-lactone in denosomin and the triene moiety in VD3 was effective to enhance the nerve re-extension activity in amyloid beta (A beta)-damaged neurons.

  DOI：

  10.1021/acs.orglett.5b03138
• 作为产物：
  描述：

  (S)-(+)-2,3,7,7A-四氢-7A-甲基-1H-茚-1,5(6H)-二酮 以70.9的产率得到(3aR,4S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-dione
  参考文献：
  名称：

  Process for producing vitamin D derivative using convergent method

  摘要：

  提供了一种新的生产[{(5Z,7E)-(1S,3R,20S)-1,3-二羟基-9,10-去氢孕酮-5,7,10(19),16-四烯-20-基}氧基]-N-(2,2,3,3,3-五氟丙基)乙酰胺的方法，该方法如下反应方案所示：一种用于实施该方法的中间体，以及生产该中间体的方法。

  公开号：

  US08173824B2

文献信息

• Short-step synthesis and structure-activity relationship of cortistatin A analogs
  作者：Naoyuki Kotoku、Aoi Ito、Shunichi Shibuya、Kanako Mizuno、Aki Takeshima、Masaki Nogata、Motomasa Kobayashi

  DOI：10.1016/j.tet.2017.01.042

  日期：2017.3

  An improved method for synthesizing structurally simplified analogs of cortistatin A (1), a novel anti-angiogenic steroidal alkaloid from a marine sponge, was developed. In contrast to previous methods, step- and redox-economical synthesis was achieved using a known α-bromoketone as the starting material. The structure-activity relationship study revealed that the isoquinoline portion was strictly recognized

  开发了一种改进的方法，用于从海洋海绵中合成皮质抑素A（1）（一种新型的抗血管生成类固醇生物碱）的结构简化类似物。与以前的方法相比，使用已知的α-溴代酮作为起始原料，可以实现分步和氧化还原经济的合成。结构-活性关系研究表明，异喹啉部分被目标分子严格识别。出人意料的是，在A环结构上引入乙酰胺部分极大地增强了对内皮细胞的选择性抗增殖活性。这种新方法可以轻松地用于克级合成，并使我们能够制备各种类似物，这些类似物侧重于侧链和A环结构的参与。
• OXA-STEROIDS DERIVATIVES AS SELECTIVE PROGESTERONE RECEPTOR MODULATORS
  申请人：Kang Fu-An

  公开号：US20070197635A1

  公开（公告）日：2007-08-23

  The present invention is directed to novel 7-oxa-estra-4,9-diene-3,17-dione derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by at least one progesterone or glucocorticoid receptor.

  本发明涉及新颖的7-氧杂雌甾-4,9-二烯-3,17-二酮衍生物，含有它们的药物组合物以及它们在治疗至少受孕激素或糖皮质激素受体调节的疾病和症状中的应用。
• Process for producing vitamin D derivative using convergent method
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US08173824B2

  公开（公告）日：2012-05-08

  There are provided a novel process for producing [(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl}oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide, which process is shown in the following reaction scheme: an intermediate useful for carrying out the process, and a process for producing the intermediate.

  提供了一种新的生产[(5Z,7E)-(1S,3R,20S)-1,3-二羟基-9,10-去氢孕酮-5,7,10(19),16-四烯-20-基}氧基]-N-(2,2,3,3,3-五氟丙基)乙酰胺的方法，该方法如下反应方案所示：一种用于实施该方法的中间体，以及生产该中间体的方法。
• Intermediates for the Synthesis of Vitamin D
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1031552A1

  公开（公告）日：2000-08-30

  The invention relates to an improved process for preparing [(3aR,4S,7aS)-4-bromooctahydro-7a-methyl-1H-indene-1,5-dione]. (S)-(+)-2,3,7,7a-tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminum hydride and hexamethylphosphoric triaminde in the presence of a catalyst of the formula R-Cu, wherein R is and R1, R2 and R3 are each, independently, selected from the group consisting of C1-7 alkyl, phenyl, phenyl substituted by at least one C1-4 alkyl group, benzyl, or benzyl substituted by at least one C1-4 alkyl groups to form a reductate. The reductate is then treated with a bromine-containing electrophile to yield (3aR,4S,7aS)-4-bromooctahydro-7a-methyl-1H-indene-1,5-dione.

  本发明涉及一种制备[(3aR,4S,7aS)-4-溴八氢-7a-甲基-1H-茚-1,5-二酮]的改进工艺。(S)-(+)-2,3,7,7a-四氢-7a-甲基-1H-茚-1,5(6H)-二酮在式 R-Cu 的催化剂存在下，通过与氢化二异丁基铝和六甲基三脒磷反应进行还原，其中 R 为 和 R1、R2 和 R3 各自独立地选自 C1-7 烷基、苯基、被至少一个 C1-4 烷基取代的苯基、苄基或被至少一个 C1-4 烷基取代的苄基组成的组，形成还原剂。然后用含溴亲电子体处理还原剂，得到 (3aR,4S,7aS)-4-溴八氢-7a-甲基-1H-茚-1,5-二酮。
• Daniewski, Andrzej Robert; Kiegiel, Jaroslaw; Piotrowska, Emilia, Liebigs Annalen der Chemie, 1988, p. 593 - 594
  作者：Daniewski, Andrzej Robert、Kiegiel, Jaroslaw、Piotrowska, Emilia、Warchol, Tadeusz、Wojciechowska, Wanda

  DOI：——

  日期：——