[(1S,2R,4aS,8aS)-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]methanol | 247905-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: [(1S,2R,4aS,8aS)-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]methanol
• CAS: 247905-61-9
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: JWJKKVIKMZOKJH-NEBZKDRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(1S,2R,4aS,8aS)-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]methanol 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde
  参考文献：
  名称：

  New total synthesis of (+)-ambrein

  摘要：

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.015
• 作为产物：
  描述：

  (4Aalpha)-2-亚甲基-5,5,8Abeta-三甲基十氢萘-1beta-甲醇 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以10 mg的产率得到[(1S,2R,4aS,8aS)-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]methanol
  参考文献：
  名称：

  Ichthyotoxic Phloroglucinol Derivatives from Dryopteris fragrans and Their Anti-tumor Promoting Activity.

  摘要：

  利用日本鳉鱼（Oryzias latipes，日文名；medaka）进行毒性定向分馏，从香干（Dryopteris fragrans）的全草中分离出了两种新的鱼毒性化合物：aspidin PB (8) 和 dryofragin (9)，以及三种已知的氯葡萄糖醇衍生物 (1-3) 和五种萜类化合物。新化合物的结构是通过光谱方法（包括二维核磁共振技术）确定的。在分离出的化合物中，aspidin PB (8)、dry-ofragin (9) 和 1-5 对青鱼具有很强的鱼毒活性，24 小时后的中位耐受极限（TLm）为 1.2-4.3 μg/ml。这些对鱼类具有毒性的化合物还对十四碳酰基光稳定剂 13-乙酸酯诱导的 Epstein-Barr 病毒早期抗原（EBV-EA）的活化具有有效的抑制作用。Aspidin BB (2) 和 albicanol (4) 对 EBV-EA 的活化有很强的抑制作用，能显著抑制小鼠皮肤的体内两阶段癌变。

  DOI：

  10.1248/cpb.48.1190

文献信息

• New total synthesis of (+)-ambrein
  作者：Naoko Fujiwara、Masako Kinoshita、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2006.11.015

  日期：2006.11

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.
• Ichthyotoxic Phloroglucinol Derivatives from Dryopteris fragrans and Their Anti-tumor Promoting Activity.
  作者：Hideyuki ITO、Takashi MURANAKA、Kazuko MORI、Zhe-Xiong JIN、Harukuni TOKUDA、Hoyoku NISHINO、Takashi YOSHIDA

  DOI：10.1248/cpb.48.1190

  日期：——

  Two new ichthyotoxic compounds, aspidin PB (8) and dryofragin (9), along with three known phloroglucinol derivatives (1-3) and five terpenoids, were isolated from the whole herbs of Dryopteris fragrans by toxicity-directed fractionation using Oryzias latipes (Japanese name; medaka). The structures of the new compounds were determined by spectroscopic methods including 2D NMR techniques. Amongst the isolates, aspidin PB (8), dry-ofragin (9), and 1-5 exhibited potent ichthyotoxic activity against medaka with a median tolerance limit (TLm after 24 h) of 1.2-4.3 μg/ml. These compounds which are toxic to fish also had a potent inhibitory effect on the activation of Epstein-Barr virus early-antigen (EBV-EA) induced by tetradecanoyl phorbol 13-acetate, which is an in vitro short-term assay for anti-tumor promoting agents. Aspidin BB (2) and albicanol (4), which exhibited strong inhibitory effects on the EBV-EA activation, significantly suppressed an in vivo two-stage carcinogenesis on mouse skin.

  利用日本鳉鱼（Oryzias latipes，日文名；medaka）进行毒性定向分馏，从香干（Dryopteris fragrans）的全草中分离出了两种新的鱼毒性化合物：aspidin PB (8) 和 dryofragin (9)，以及三种已知的氯葡萄糖醇衍生物 (1-3) 和五种萜类化合物。新化合物的结构是通过光谱方法（包括二维核磁共振技术）确定的。在分离出的化合物中，aspidin PB (8)、dry-ofragin (9) 和 1-5 对青鱼具有很强的鱼毒活性，24 小时后的中位耐受极限（TLm）为 1.2-4.3 μg/ml。这些对鱼类具有毒性的化合物还对十四碳酰基光稳定剂 13-乙酸酯诱导的 Epstein-Barr 病毒早期抗原（EBV-EA）的活化具有有效的抑制作用。Aspidin BB (2) 和 albicanol (4) 对 EBV-EA 的活化有很强的抑制作用，能显著抑制小鼠皮肤的体内两阶段癌变。