exo-4-protoadamantanol | 55870-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: exo-4-protoadamantanol
• 英文别名: 4-protoadamantanol；4-Hydroxyprotoadamantan；tricyclo[4.3.1.03,8]decan-4-ol
• CAS: 55870-65-0
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: JZNAWKREMOWXER-UHFFFAOYSA-N

物化性质

• 沸点：
  255.2±8.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  exo-4-protoadamantanol 在 三氟乙酸 作用下， 反应 6.0h， 生成 2-adamantyl trifluoroacetate
  参考文献：
  名称：

  Mechanism of addition of neat trifluoroacetic acid to protoadamantene

  摘要：

  DOI：

  10.1021/ja00545a015
• 作为产物：
  描述：

  4-protoadamantanone 在 lithium aluminium tetrahydride 作用下， 以90%的产率得到exo-4-protoadamantanol
  参考文献：
  名称：

  Mechanism of addition of neat trifluoroacetic acid to protoadamantene

  摘要：

  DOI：

  10.1021/ja00545a015

文献信息

• Evaluation of Antiproliferative Effect of N-(alkyladamantyl)phthalimides In vitro
  作者：Margareta Horvat、Lidija Uzelac、Marko Marjanović、Nikola Cindro、Oliver Franković、Kata Mlinarić-Majerski、Marijeta Kralj、Nikola Basarić

  DOI：10.1111/j.1747-0285.2011.01305.x

  日期：2012.4

  A series of (1‐adamantyl)phthalimides, 1–4, and (2‐adamantyl)phthalimides, 5–8, characterized by different chain length between the adamantyl and the phthalimide moiety were synthesized, as well as 1‐ and 2‐adamantylphthalimides substituted by nitro 9, 10, and amino group 11, 12, and phthalimides bearing homoadamantyl 13 and protoadamantyl substituent 14 and 15. The compounds were tested for antiproliferative activity in vitro on a series of five human cancer lines: MCF‐7 (breast carcinoma), SW 620 (colon carcinoma), HCT 116 (colon carcinoma), MOLT‐4 (acute lymphoblastic leukemia), H 460 (lung carcinoma), and a non‐tumor cell line HaCaT (human keratinocytes). All compounds except nitro derivatives 9 and 10 exhibited antiproliferative activity. The activity was generally better in the 2‐adamantyl series 5–8 and in the compounds having the longest alkyl spacers as in 4 and 8, or with an amino group as in 9 and 10. The most active compounds with the propylene spacer 4 and 8 showed the highest selectivity toward tumor cells. The activity was found to be due to a delay in the progress through the cell cycle at G1/S phase.
• NORDLANDER J. E.; HAKY J. E.; LANDINO J. P., J. AM. CHEM. SOC., 1980, 102, NO 25, 7487-7493
  作者：NORDLANDER J. E.、 HAKY J. E.、 LANDINO J. P.

  DOI：——

  日期：——
• Mechanism of addition of neat trifluoroacetic acid to protoadamantene
  作者：J. Eric Nordlander、Jerome E. Haky、John P. Landino

  DOI：10.1021/ja00545a015

  日期：1980.12