(1R,4aR,7R,8aR,10aS)-7-Hydroxymethyl-1,4a,7-trimethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester | 187722-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (1R,4aR,7R,8aR,10aS)-7-Hydroxymethyl-1,4a,7-trimethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester
• 英文别名: methyl (1R,4aR,7R,8aR,10aS)-7-(hydroxymethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate
• CAS: 187722-32-3
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: DVXBYMHCHSBOTJ-IMWRDGPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4aR,7R,8aR,10aS)-7-Hydroxymethyl-1,4a,7-trimethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 乙醚 为溶剂， 生成 Acetic acid (1R,4aR,7R,8aR,10aS)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-ylmethyl ester
  参考文献：
  名称：

  Stereoselective Construction of C-13 Quaternary Carbon Unit of Isopimarane Diterpene and Its Synthetic Application to Isopimarol Diterpene

  摘要：

  Highly stereoselective construction of the C-13 quaternary carbon unit of isopimarane diterpene has been achieved by two consecutive alkylations of the tricyclic enone intermediate which was straightforwardly derived from the known decalone system. In addition, this procedure has been expanded to the general synthetic route to isopimarane diterpenes.

  DOI：

  10.1080/00397919708003329
• 作为产物：
  描述：

  methyl (1R,4aR,8aS)-1,4a-dimethyl-5-[(E)-2-phenylsulfanylethenyl]-2,3,4,7,8,8a-hexahydronaphthalene-1-carboxylate 在 sodium tetrahydroborate 、 四氯化锡 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.67h， 生成 (1R,4aR,7R,8aR,10aS)-7-Hydroxymethyl-1,4a,7-trimethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  抗炎剂（-）-棘酸的对映选择性合成。

  摘要：

  描述了有效的抗炎药（-）-棘酸（1）的对映选择性合成。成功的策略与（-）-Wieland-Miescher酮（10）背离，后者易于以两种对映体形式使用，构成了向完全功能化的AB环系统1的起点。 A环的C4中心，生成化合物32为单个立体异构体。C环1的构建是通过含硫二烯43与甲基丙烯醛（36）之间的Diels-Alder反应完成的，脱硫和进一步官能化后生成合成的棘酸。

  DOI：

  10.1021/jo0159035

文献信息

• Interleukin-1 and tumor necrosis factor-alpha modulators; syntheses of such modulators and methods of using such modulators
  申请人：Palladino Michael A.

  公开号：US20080064753A1

  公开（公告）日：2008-03-13

  Described herein are chemical compounds and pharmaceutical compositions, including novel chemical compounds and pharmaceutical compositions thereof, useful in the treatment of various diseases and disease states. Also described are methods of synthesizing natural products and novel, structurally-related chemical compounds. More particularly, disclosed are new analogs of and processes for the preparation of compounds and pharmaceutical compositions thereof useful in the treatment of, for example, inflammation, cancer, multiple myeloma, cachexia, cardiovascular disease, anti-infectious, diabetes, otitis media, sinusitis and transplant rejection.

  本文描述了一些化合物和药物组合物，包括新颖的化合物和药物组合物，它们可用于治疗各种疾病和疾病状态。同时，还描述了合成天然产物和新的、结构相关的化合物的方法。更具体地，披露了新的模拟物和制备它们的化合物和药物组合物的过程，这些化合物和药物组合物可用于治疗炎症、癌症、多发性骨髓瘤、消瘦症、心血管疾病、抗感染、糖尿病、中耳炎、鼻窦炎和移植排斥等疾病。
• INTERLEUKIN-1 AND TUMOR NECROSIS FACTOR-ALPHA MODULATORS; SYNTHESES OF SUCH MODULATORS AND METHODS OF USING SUCH MODULATORS
  申请人：Palladino Michael A.

  公开号：US20110160309A1

  公开（公告）日：2011-06-30

  Described herein are chemical compounds and pharmaceutical compositions, including novel chemical compounds and pharmaceutical compositions thereof, useful in the treatment of various diseases and disease states. Also described are methods of synthesizing natural products and novel, structurally-related chemical compounds. More particularly, disclosed are new analogs of and processes for the preparation of compounds and pharmaceutical compositions thereof useful in the treatment of, for example, inflammation, cancer, multiple myeloma, cachexia, cardiovascular disease, anti-infectious, diabetes, otitis media, sinusitis and transplant rejection.

  本文描述了化学化合物和药物组合物，包括新型化学化合物和药物组合物，用于治疗各种疾病和疾病状态。还描述了合成天然产物和新的结构相关化学化合物的方法。更具体地，披露了用于治疗炎症、癌症、多发性骨髓瘤、消瘦、心血管疾病、抗感染、糖尿病、中耳炎、鼻窦炎和移植排斥等疾病的化合物和药物组合物的新类似物和制备方法。
• Stereoselective Synthesis of (−)-Acanthoic Acid
  作者：Taotao Ling、Bryan A. Kramer、Michael A. Palladino、Emmanuel A. Theodorakis

  DOI：10.1021/ol0060578

  日期：2000.7.1

  GRAPHICSThe first stereoselective synthesis of (-)-acanthoic acid (1) has been designed and accomplished. Our synthetic plan departs from (-) Wieland-Miesher ketone (7) and calls upon a Diels-Alder cycloaddition reaction for the construction of the C ring of 1. The described synthesis confirms the proposed stereochemistry of 1 and represents an efficient entry into an unexplored class of biologically active diterpenes.
• INTERLEUKIN-1 AND TUMOR NECROSIS FACTOR-A MODULATORS; SYNTHESES OF SUCH MODULATORS AND METHODS OF USING SUCH MODULATORS
  申请人：Nereus Pharmaceuticals, Inc.

  公开号：EP1912932B1

  公开（公告）日：2012-05-02
• US8133915B2
  申请人：——

  公开号：US8133915B2

  公开（公告）日：2012-03-13