(4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone | 188120-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone
• 英文别名: (6R,7R,8S)-8-t-Butyldimethylsilyloxy-6,7-dimethylbicyclo[4,4,0]deca-1-en-3-one；(4aR,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-4a,5-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 188120-44-7
• 化学式: C₁₈H₃₂O₂Si
• 分子量: 308.536
• InChiKey: XHGBCEVSDNWJBC-QANKJYHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone 在 selenium(IV) oxide 、 camphor-10-sulfonic acid 、 zinc(II) chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 14.5h， 生成 PF1092C
  参考文献：
  名称：

  Total synthesis of progesterone receptor ligands, (−)-PF1092A, B and C

  摘要：

  Microbial metabolites (-)-PF1092A, B and C belonging to an eremophilane sesquiterpene group are synthesized from (R)-5-hydroxymethyl-2(5H)-furanone through the SnCl4 promoted cyclization of an alpha-keto methyl sulfone and dimethyl acetal followed by a Stork annulation which gives the octalone core. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00042-7
• 作为产物：
  描述：

  5-(甲氧基)2-(5H)-二氧三环酮 在 吡啶 、 2,6-二甲基吡啶 、 disodium hydrogenphosphate 、 aluminum amalgam 、 正丁基锂 、 三甲基氯硅烷 、 Amberlyst 15 、 草酰氯 、 TEA 、 camphor-10-sulfonic acid 、 甲基锂 、 sodium methylate 、 四氯化锡 、 二甲基亚砜 、 六甲基二硅氮烷 、 lithium hexamethyldisilazane 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 (4aR,5R,6S)-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone
  参考文献：
  名称：

  Total synthesis of progesterone receptor ligands, (−)-PF1092A, B and C

  摘要：

  Microbial metabolites (-)-PF1092A, B and C belonging to an eremophilane sesquiterpene group are synthesized from (R)-5-hydroxymethyl-2(5H)-furanone through the SnCl4 promoted cyclization of an alpha-keto methyl sulfone and dimethyl acetal followed by a Stork annulation which gives the octalone core. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00042-7

文献信息

• Tetrahydronaphthofuranone derivatives and process for producing the same
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：US06255339B1

  公开（公告）日：2001-07-03

  Compounds represented by the following formula (I) and pharmaceutically acceptable salts thereof are disclosed. The compounds have progesterone receptor binding inhibitory activity and, hence, can be used as therapeutic and prophylactic agents for progesterone-related diseases. Specifically, they are useful as abortifacients, oral contraceptive pills, carcinostatic agents for breast cancer and ovarian cancer, therapeutic agents for endometriosis, meningioma, and myeloma, and therapeutic and prophylactic agents for osteoporosis and climacteric disturbance. wherein R1 and R2 represent a hydroxyl group, alkyloxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkoxyalkyloxy, cycloalkyloxy containig one oxygen atom, aralkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, aryloxy carbonyloxy, aralkylcarbonyloxy, aromatic acyloxy, heteroaromatic acyloxy, saturated heterocyclic carbonyloxy, alkylsulfonyloxy, aromatic sulfonyloxy, alkylcarbamoyloxy, aromatic carbamoyloxy, alkylcarbonylamino, or aromatic acylamino, provided that R1 may further represent a hydrogen atom, alkyl, alkenyl, or alkynyl; and R3, R4, and R5 each independently represent a hydrogen atom, alkyl or alkenyl.

  以下式(I)表示的化合物及其可药用的盐被披露。这些化合物具有抑制孕酮受体结合的活性，因此可以用作治疗和预防与孕酮相关疾病的药物。特别是，它们可用作堕胎药、口服避孕药、用于乳腺癌和卵巢癌的抗癌剂、用于治疗子宫内膜异位症、脑膜瘤和多发性骨髓瘤的治疗剂，以及用于治疗骨质疏松症和更年期障碍的治疗和预防药物。 其中 R1和R2代表羟基、烷氧基、烯氧基、炔氧基、环烷氧基、烷氧基烷氧基、含有一个氧原子的环烷氧基、芳烷氧基、烷基碳酰氧基、烯基碳酰氧基、炔基碳酰氧基、环烷基碳酰氧基、烷氧基碳酰氧基、芳氧基碳酰氧基、芳烷基碳酰氧基、芳香酰氧基、杂芳酰氧基、饱和杂环碳酰氧基、烷基亚磺酰氧基、芳香亚磺酰氧基、烷基氨基甲酰氧基、芳香氨基甲酰氧基、烷基碳酰胺基或芳香酰氨基，条件是R1还可以进一步代表氢原子、烷基、烯基或炔基；R3、R4和R5各自独立地代表氢原子、烷基或烯基。
• Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source
  作者：Hiroko Akao、Hiromasa Kiyota、Takao Nakajima、Takeshi Kitahara

  DOI：10.1016/s0040-4020(99)00407-x

  日期：1999.6

  Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Total synthesis of progesterone receptor ligands, (−)-PF1092A, B and C
  作者：Kuniaki Tatsuta、Shohei Yasuda、Ken-ichi Kurihara、Kiyoshi Tanabe、Rie Shinei、Tsuneo Okonogi

  DOI：10.1016/s0040-4039(97)00042-7

  日期：1997.2

  Microbial metabolites (-)-PF1092A, B and C belonging to an eremophilane sesquiterpene group are synthesized from (R)-5-hydroxymethyl-2(5H)-furanone through the SnCl4 promoted cyclization of an alpha-keto methyl sulfone and dimethyl acetal followed by a Stork annulation which gives the octalone core. (C) 1997 Elsevier Science Ltd.